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The Study of the Optical Properties of C60 Fullerene in Different Organic Solvents

  • Teguh Endah Saraswati EMAIL logo , Umam Hasan Setiawan , Mohammad Rifki Ihsan , Isnaeni Isnaeni and Yuliati Herbani
Published/Copyright: December 31, 2019
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Open Chemistry
From the journal Open Chemistry Volume 17 Issue 1

Abstract

C60 fullerene exhibits unique optical properties that have high potential for wide photo-optical applications. To analyze the optical properties of C60, its excitation and emission properties were studied using UV-Vis absorption and photoluminescence (PL) spectroscopy, which were performed in various, non-polar organic solvents such as toluene, xylene, and trichloroethylene (TCE). The C60 solutions in toluene, xylene, and TCE displayed similar excitation bands at 625, 591, 570, 535, and 404 nm corresponding to Ag → T1u and Ag → T1g transitions. However, these bands differed from the solid C60 observed by UV-Vis diffuse reflectance spectroscopy. The two emission band energies of C 60 solution in toluene and xylene were nearly the same (1.78 and 1.69 eV), whereas the C60 solution in TCE was shifted to 1.72 and 1.65 eV. Because the polarity of TCE is higher than that of toluene and xylene, the PL spectrum of the C 60 solution in TCE was red-shifted. The PL spectroscopy had a better capability than UV-Vis absorbance spectroscopy to distinguish the different interactions between C60 and the organic solvents due to their different solvent polarities.

Keywords: C60; UV-Vis absorption; photoluminescence; solvatochromism; solvent polarity

1 Introduction

The allotropes of carbon nanostructure material—such as graphite, graphene, diamond, fullerenes, carbon nanotubes, amorphous carbon, and carbyne—have received great interest due to their chemical and physical properties. Each allotrope exhibits different properties depending on its carbon structure and size. According to carbon hybridization, graphite and graphene have sp2-hybridized carbon atoms, while a diamond has sp3- hybridized carbon atoms. Amorphous carbon mostly consists of sp2-hybridized carbon atoms, and carbyne has sp-hybridized carbon atoms. The other carbon allotrope materials—fullerenes and carbon nanotubes—have quasi-sp2 hybridization [1].

Fullerene takes the spherical shape of graphene and was discovered through the laser evaporation of graphite by Kroto in 1985 [2], who won a Nobel Prize in 1996 for this discovery. Unlike graphite or graphene, which are predicted to be in planar geometry in their stable form, spherical fullerene has a pyramidalization angle (θσπ – 90) depending on the number of carbon atoms. This pyramidalization angle can force carbon atoms to have a spherical geometry. One example of the pyramidalization angle belonging to C60 fullerene is 11.6o [3, 4], which means that a 101.6o angle was formed between the σ and π orbitals in a carbon atom. Among various types of fullerene, the most commonly known and most stable species is Buckminsterfullerene, or C60 [5, 6, 7]. C60 fullerene is soluble in non-polar or slightly polar organic solvents. The non-polar solvents, such as toluene, o-xylene, carbon disulfide (CS2), dichlorobenzene (DCB), etc., are commonly used to extract the fullerenes from freshly prepared carbon soot after the synthesis process.

The growing interest in C60 has encouraged more studies in various fields, the number of which has continued to grow since the discovery of C60 fullerene, and C60 has been applied in various applications due to its unique chemical and physical properties. These applications include supercapacitors [8, 9], hydrogen

storage [10, 11], nanoelectronics [12, 13], and biomedical applications such as gene and drug delivery [14, 15]. Additionally, the quasi-sp2- hybridized carbon belonging to C60 supports the high electronic conductivity in charge transportation and separation [16]. Therefore, C60 and its derivatives have many potential uses in optics due to their electron-accepting characteristics and photophysical properties.

C 60 exhibits several unique electronic properties related to its optical characteristics and photoluminescence (PL). PL is a process in which a molecule spontaneously emits light after absorbing a photon, which enables the electrons to be excited to a higher electronic state. The emitted light is a result of the electron returning to its lower energy state, which is known as fluorescence and phosphorescence [17]. In general, the illustration of the excitation-emission mechanism is commonly understood using the Perrin-Jablonski diagram [18]. Carbon nanomaterial exhibits different PL characteristics depending on its architecture, size, morphology, and structure. For example, diamond and bulk graphite do not exhibit PL due to their infinite carbon networks. However, a spherical fullerene is able to produce strongly environment-dependent PL, which is emitted from the lowest energy singlet-electronic excited state to the ground state in the Vis-NIR region [19].

Theoretically, the PL process is influenced by the environment, the solvent, and the temperature. In general, at low temperature, the PL of fullerene is weak. Similarly, if the fullerene solubility is low in solvent, then the PL will also be weak. Furthermore, because fullerenes are good electrophiles, they can form both ground and excited-state complexes with many aromatic solvents, resulting in strong solvatochromism [19]. In the solvatochromism phenomenon, the intermolecular interactions affect the excitation and emission properties induced by the solute-solvent interaction [20].

The optical properties of fullerene have been widely investigated in different solvents by spectroscopy, and the published studies on the comparisons of C60 optical properties have agreed on solvents with significant different polarity, including toluene [21, 22, 23, 24], o-xylene, dichlorobenzene (DCB) [25], hexane [22, 26], cyclohexane [27], methylcyclohexane, CS2 [28], acetonitrile [23], alkanes [29], and water [30, 31, 32]. However, the interpretation of the findings has revealed unpredictable results due to the unknown dynamic phenomenon caused by inter and intramolecular interactions. Since the chemical structures and polarity of the solvents influence the optical properties of the C60 solution [33, 34, 35], intermolecular interactions such as Coulomb and dispersion forces and electron-charge transfer forces might be produced by the solute-solvent interactions. These interactions are defined by the solvent polarity and are expected to have a significant role in the photochemistry of fullerenes. Besides the intermolecular interaction, the other factor that should also be considered is the intra-molecular interaction involving the Jahn-Teller (JT) distortions and Herzberg-Teller (HT) vibronic coupling [18, 20, 28, 29, 36, 37].

Due to its unique optical properties, C60 is used in various applications, including solar cells [38, 39], light to electrical energy converters in photovoltaic devices [40, 41, 42, 43, 44], photocatalysts [45, 46, 47, 48, 49], phototherapy [50, 51], bioimaging [52, 53], and biosensing [54, 55, 56]. C60 possibly exhibits the optical response depending on the changing of the environment; however, the relevant studies on this sensitive response are still limited. Therefore, this study examined the optical properties of C60 fullerene, including the excitation and emission characteristics found in organic non-polar solvents with slightly different polarity.

To study the sensitive optical response of C 60, different solvents were selected that had similar chemical structure and polarity; these were toluene and xylene. Moreover, to study the polarity effect, another solvent with a slightly higher polarity compared to toluene and xylene was chosen; this solvent was trichloroethylene (TCE). These three solvents were considered suitable for studying the solvatochromism phenomenon based on the PL spectra revealed by different C60 solutions. Therefore, this study aimed to confirm that the solvents with slightly different chemical structure and polarity would responsively provide different molecular interactions with C 60 fullerene by producing spectra with apparent characteristics.

Additionally, this study compared the absorption spectra of solid C 60 and its solutions in different solvents to demonstrate the environment-sensitive optical response characteristics. A comparison to pioneering works, both theoretical and experimental, was also performed. The results reported in the present study indicated the potential use of C60 as a controllable fluorescent material in imaging and optoelectronics applications.

2 Methods

The concentration of the C60 fullerene solution was made 0.1 (w/v)% by dissolving 0.003 g C60 (95%; Hengqiu Graphene Technology [Suzhou] Co., Ltd) in 3 mL of each of the following solvents: toluene (Merck, ≥99.9%), xylene (Pudak, isomeric mixture), and TCE (Merck, ≥99.5%). An absorption spectra scan was performed on the C60 solution in these three solvents. The absorbance measurement was carried out using a spectrophotometer (MayaPro2000 Ocean Optics) with a halogen lamp source (300 nm to 1100 nm). The solution was put in a quartz cuvette, and its absorbance was measured at wavelengths from 300 nm to 1100 nm. The chemical information of functional groups and the purity and morphological properties of the solid C 60 were examined by Fourier transformed infrared (FTIR; IRPrestie-21, Shimadzu), Raman spectrometer (Modular Raman Spectroscopy – iHR550, Horiba), and scanning electron microscopy (SEM; FEI Inspect-S50), respectively. The solid C60 was also characterized by using UV-Vis diffuse reflectance spectroscopy (Pharmaspec UV1700, Shimadzu), in which the data was further compared to the optical data of C60 in solvents.

The PL properties of the C60 solutions in different solvents were investigated using a home-made PL spectrophotometer consisted of a spectrograph (MayaPro2000 Ocean Optics), a laser diode (420 nm, 5 mW), and the plano-convex lenses. The radiated laser was caught by the first lens and focused on the cuvette of the sample. The laser hit the clear front side of the cuvette at a 45o angle. This light beam of the emission was then reflected onto the second lens. The second lens gathered the light scattered from the cuvette, and this light was then refocused by the third lens, allowing the light to be caught by the spectrometer via a fiber optic and then analyzed by a computer. To learn the band energies observed in the absorption and PL spectra, equation (1) was applied.

(1)E=hcλ

where E is energy, h is Planck’s constant (6.63 × 10−34 J s), c is the speed of light, and λ is wavelength.

Ethical approval: The conducted research is not related to either human or animal use.

3 Results and Discussion

The C60 geometric structure has Ih symmetry in the solid phase, as seen in Figure 1(a). If a possible reaction causes C60 symmetry to change, the C60 optical properties can also change. The solid C60 was firstly characterized by FTIR, Raman spectrometer, and SEM to test the original characteristics compared to relevant references. The FTIR and Raman spectra of the solid C60 are presented in Figure 1(b) and (c), respectively. The C60 was expected to have only four infrared active vibrational modes (of species T1u) occurring at about 1600±200, 1300±200, 630±100, and 500±50 cm-1 [57].

Figure 1 (a) The Ih symmetry structure of C60, (b) FTIR, (c) Raman spectrum of solid C60, and (d-e) the SEM imaging of solid C60 at a different magnification.
Figure 1

(a) The Ih symmetry structure of C60, (b) FTIR, (c) Raman spectrum of solid C60, and (d-e) the SEM imaging of solid C60 at a different magnification.

As shown in Figure 1(b), the spectrum of the solid C60 revealed several relevant absorption peaks at 526.6, 575.8, 1181.4, and 1428.3 cm-1 (attributed to C–C vibrational modes) and 3460 cm-1 (attributed to O–H stretching). All these peaks were found in agreement with previous studies [30, 57, 58, 59]. The O–H stretching peak had broad shape with less intensity, which strongly suggested that it came from air adsorbed in the material’s pores rather than as a hydroxyl functional group attached to carbon. This suggestion was supported by the fact that no broad peak C–OH observed at 1107 cm-1 was found [30]. The observation of these peaks showed that the C60 sample used in this study was original C60 with high purity.

Raman spectrometry was also a useful technique for the characterization of disorder in carbon-based materials. The analysis of specific features in the Raman spectra provided a way to estimate the crystallite sizes in disordered carbons [60]. Therefore, to confirm that the C60 sample in a solid state had good and stable properties, the Raman spectrum of sample was characterized, as shown in Figure 1(c). The vibrational modes of the solid C60 were divided into intermolecular vibrations (or lattice modes) and intra-molecular vibrations (simply molecular modes), and the first mode lay at lower frequencies, while the latter one lay at a higher frequency (above 270 to 1700 cm-1). The higher frequency was observed to be more dominant. The characteristics of the Raman spectra were in accordance with the literature [61, 62], which previously reported several peaks at a Raman shift of 272, 432, 496, 709, 772, 1099, 1249, 1422, 1467, and 1573 cm-1. Additionally, the Raman active modes had 2Ag and 8Hg symmetry. The C60 spectrum had two relatively sharp lines at around 496 and 1467 cm-1, known as the breathing mode, Ag(1), and pentagonal pinch mode, Ag(2), respectively [61, 62]. 1Ag is the ground state of C60 issued from the closed shell electron configuration of ag2t1u6hg10t2u6gu8gu8hg10hu10[26]. The other peaks at 272, 432, 709, 772, 1099, 1249, 1422, and 1573 cm-1 corresponded to Hg(1) to Hg(8) modes [61, 62]. The sharpness of the bands indicated that the bonds were mostly uniform in nature.

According to the SEM analysis, as shown in Figure 1(d) to (e), the solid C 60 consisted of particulate aggregated C60 ~200 nm with a regular spherical form. Smaller-sized particle grains were also observed, as indicated by the red rectangle in Figure 1(d) and emphasized in Figure 1(e).

Many researchers have studied the optical properties involving the fluorescence of C60 as revealed in different solvents. This study, however, used three kinds of organic solvents—toluene, xylene, and TCE. In this experiment, the color of the C 60 solution in both the toluene and xylene solvents turned purple, and it was a darker purple in the TCE, as seen in Figure 2. The same purple color was seen in the toluene and xylene solvents possibly due to the similar structure of these two solvents consisting of a benzene ring and methyl group. In contrast, TCE has a different structure consisting of a halogenated hydrocarbon compound with no benzene ring.

Figure 2 The C60 solution in different organic solvents: (a) toluene, (b) xylene, and (c) TCE.
Figure 2

The C60 solution in different organic solvents: (a) toluene, (b) xylene, and (c) TCE.

As mentioned in the introduction, due to fullerene structure consists of an sp2-hybridized carbon atom, C60 is mostly dissolved in a non-polar organic solvent with different solubility [63]. The solubility of fullerene is determined by a geometric factor and the specific molecular interactions between fullerene and the solvent molecules. The interactions are influenced by several solvent properties, such as polarizability, polarity, molecular size, and cohesive energy density [63]. The polarizability is defined by the ease of electron cloud distortion that causes the originally non-polar molecule or atom to acquire a dipole moment. The polarity indicates the distribution of the electrical charge over the molecules and is closely related to the relative electronegativities of the elements. Applying the “like-dissolves-like” concept, the identical polarizability and polarity for solute and solvents achieves better interaction between them, thus increasing solubility. For instance, as Ruoff et al. [63] reported, the non-polar sp2 carbon atom characteristics of C60 have better solubility in xylene (5.2 mg/L) than in toluene (2.8 mg/L). The solubility of C60 in TCE was found to be less than the solubility in both toluene and xylene, at 1.4 mg/L. The solubility of C60 in alkanes such as n-pentane, n-hexane, etc. was very low (~0.005 to 0.04 mg/L), far from the solubility in toluene and xylene [63].

The illustrations of the interaction between C60 and the solvents are presented in Figure 3. The three solvents—toluene, xylene, and TCE—had distinguished dipole moments of 0.31 D, 0.45 D, 0.31 D, 0 D, and 0.81 D, for toluene, o-xylene, m-xylene, p-xylene, and TCE, respectively [64]. These moments might have corresponded to their dielectric constants [63, 65]. For comparison purposes, C60 had a dipole moment of 0.47 D [63]. In the interaction between C60 and toluene or xylene, due to the similar chemical structure consisting of a hexagonal ring of carbon, C60 acted as a π-acceptor, as illustrated in Figure 3(a) to (b). Therefore, the interaction between C60 and toluene/xylene occurred as a weaker intermolecular interaction—the Van der Waals interaction—which accounted for the London dispersion forces, particularly the π – π interactions between the hexagonal ring of carbon as shown in Figure 3(a) and (b).

Figure 3 Illustration of the presumptive interaction of C60 with three solvents: (a) toluene, (b) xylene, and (c) TCE.
Figure 3

Illustration of the presumptive interaction of C60 with three solvents: (a) toluene, (b) xylene, and (c) TCE.

In contrast, due to the slightly polar chemical structure of TCE (as compared to toluene/xylene, even though all the solvents were non-polar and organic), the interaction between C60 and TCE, as shown in Figure 3(c), occurred as dipole-induced dipole intermolecular interaction, which is defined as the interaction between the permanent dipole belonging to TCE and the induced dipole of the C 60. Moreover, C 60 acted as an effective electron acceptor, while TCE acted as the potent donor electron. The TCE molecules were adducted to C60 through charge transfer, similar to the interaction between fullerene and dimethyl sulfoxide (DMSO) reported by Zhang et al. [66]. However, regarding the “like-dissolve-like” concept, because TCE and C60 had dissimilar chemical structures, the C60 solubility in TCE was lower than in the other two solvents, which induced a weaker interaction.

Therefore, because the solute-solvent interactions might be different, the solvent induces different optical characteristics of the C60 solutions. The solvent interacts with the solute in its ground state or excited state through intermolecular bonding. In general, a polar solvent like water is capable of hydrogen bonding with the solute if the solute has a hydrogen-bonding component or if there are induced dipole-dipole interactions. In contrast, non-polar solvents can interact through polarizability via London interactions.

The UV-Vis absorption spectra of C60 in the different solvents (toluene, xylene, and TCE) are shown in Figure 4(a). The C60 solutions in the toluene, xylene, and TCE solvents revealed an absorbance around 404, 535, 570, 591, and 625 nm, as shown with arrows in Figure 4. These bands corresponded to the electronic transitions of π → π* and n → π*. This result was nearly the same as that produced by Zhang et al. [23] and Törpe and Belton [25], who found that the main absorption bands of C 60 in toluene and o-xylene occurred at a wavelength of ~407 nm in a sharp feature attributed to the lowest energy 1T1u state [67], followed by a broad absorption band in the range of 430 to 650 nm [23, 25]. This broad band was attributed to multiple vibronic excitations activated through an HT coupling orbital to the JT distorted orbital at a higher level, assigned as forbidden singlet-singlet transitions [26]. This experimental absorption feature was in agreement with the pioneering works that reported the absorption spectra of C60 in toluene [68, 69], o-xylene [25], n-hexane [26, 70, 71, 72], and N-methyl-pyrrolidine (NMP) [73].

Figure 4 The absorbance of C60 solution in different solvents: (a) full spectra and (b) emphasized spectra. The arrows show the absorption peaks, whereas the thin blue and red lines in (b) indicate the shifting of the represented peak.
Figure 4

The absorbance of C60 solution in different solvents: (a) full spectra and (b) emphasized spectra. The arrows show the absorption peaks, whereas the thin blue and red lines in (b) indicate the shifting of the represented peak.

However, the absorption spectra of C60 in toluene or xylene exhibited a comparatively positive solvatochromism (bathochromic [red] shift) of the weak n → π* absorption bands. As shown in Figure 4(b), compared to the absorption peaks observed in the spectra of C60 in toluene and xylene, those observed in the spectra of C60 in TCE slightly shifted to the lower wavelength. However, the intense π → π* transition band in the ultraviolet region was less sensitive to the solvent changes [74], which possibly indicated that there was no significant symmetry degradation of C60, even though the interaction between C 60 and the solvent was possibly different.

To study the interactions of C60 with a different solvent, the results shown in Figure 4 were compared with the absorption and reflectance spectra of the solid C60, as shown in Figure 5. The absorbance and reflectance spectra taken by a diffuse reflectance spectrometer are presented in Figure 5(a) to 5(d), which is a plot of log absorbance and reflectance (%) versus wavelength ranges from 200 to 800 nm. Figure 5(a) shows the absorption spectrum of the solid C60. The dashed rectangle in Figure 5(a) is emphasized in Figure 5(c). The emphasized absorption area of the solid C 60 shown in Figure 5(c) was presented together with the absorption spectra of the C60 solution in three different solvents for comparison. The absorption spectrum of the solid C60 was different than the C60 in solvents. All spectra presented had similar absorption bands at around 404, 590, and 625 nm. However, the absorption bands located at 535 and 570 nm were only found in the absorption spectra of the C60 solutions. The absorption peak at 404, 590, and 625 nm in the C60 solution was red-shifted to 414, 597, and 675 nm in the solid C60, as listed in Table 1, indicating the presence of stronger absorption across the gap between the highest occupied molecular orbital and lowest unoccupied molecular orbital (HOMO-LUMO) in the C 60 solution [75].

Figure 5 (a) The absorbance and (b) reflectance spectra of the solid C60; (c) and (d) are the emphasized region of the dashed rectangular regions in (a) and (b), respectively, compared to the absorption in C60 solutions in different solvents.
Figure 5

(a) The absorbance and (b) reflectance spectra of the solid C60; (c) and (d) are the emphasized region of the dashed rectangular regions in (a) and (b), respectively, compared to the absorption in C60 solutions in different solvents.

Table 1

The comparison of the observable absorption band (in nm) and energy gap (in eV) of the C60 solutions, the solid C60, and the Hückel calculation.

Absorption electronic transitionsExcitation bands of C60 in different phases
solutionasolidbsolidcC60 moleculesd
nmeVnmeVnmeVnmeV
* (1): Hu → T1u6251.996751.847351.696541.897
5912.106471.92
5702.18--
(2): Hu → T1g5352.325972.08--4952.506
(3): Hu → Hg----2614.752584.816
*(4): Hg → T1u4043.074143.004512.754352.857
(5): Hg → T1g----3373.683583.466

  1. Note: For a, b, and c, the data were taken from Figures 4 to 6, respectively; For d, the data were estimated using the Hückel calculation [80, 81]; (1) to (5) corresponds to the red upward arrows in Figure 7. *JT and HT effects possibly occurred.

Figure 5(b) shows the reflectance spectrum of C 60. The dashed rectangle in Figure 5(b) is emphasized in Figure 5(d). The arrows shown in Figure 5(a) and 5(b) represent the region where the absorption declined, which was later used to estimate the band gap energies using the Kubelka-Munk function [76, 77] as shown in equations (2) and (3), as follows:

(2)FR=1−R22R
(3)α⋅h⋅υ=Bh⋅υ−Egn

where R is reflectance. F(R) is proportional to the extinction coefficient (α). The Kubelka-Munk function modification can be applied by multiplying the function F(R) by h·υ, using the coefficient (n) associated with the electronic transition based on equation (3). B is the absorption constant, and n = ½, plotted as (α·h·υ)2 versus E for the direct allowed transition because, according to the band diagram structure, C60 had direct transition [78]. The plotting of α versus E and (α·h·υ)2 versus E is shown in Figure 6(a) to (b), respectively. The optical gap energies were then determined by an intersection of the linear extrapolation at the falling peak edge of the onset of the spectra, as shown in Figure 6(c) to (f), indicated by numbers 1 to 4.

Figure 6 The Kubelka-Munk function of the solid C60 (a-b) and the extrapolation of onset peak in four regions emphasized in (c) to (f).
Figure 6

The Kubelka-Munk function of the solid C60 (a-b) and the extrapolation of onset peak in four regions emphasized in (c) to (f).

The band energies estimated from four regions (1 to 4) were 4.75, 3.68, 2.75, 1.92, and 1.69 eV and are represented in Figure 6(c) to (f), respectively. Theoretically, the C60 crystal had a narrow-band semiconductor with the energy gap between the HOMO-LUMO of 1.5 to 2.6 eV, which is optically forbidden. The experimental evidence showed different values of the energy gap, ranging also from 1.69 to 4.82 eV (listed in Table 1). These results were also in agreement with the results published by Ren et al. [75] who reported three band energies of C60 film at 4.72, 3.65, and 2.75 eV.

According to the electronic structure of the C60 molecule, these band energies were the symmetry-allowed transitions that may be assigned as Hu → Hg (~4.6 eV), Hg → T1g (~3.6 eV), and Hg → T1u (~2.8 eV) [79]. Zhou et al. reported that solid C60 had an Egap ranging from 1.63 to 1.75 eV, which was determined from the Tauc plot calculated from the spectra taken from photothermal deflection spectroscopy [79]. Compared to the solid C60, the C60 solution had a lower wavelength (i.e., higher energy gap). This phenomenon was induced by changing the strength of the intermolecular interaction between the C60 molecules that were interfered by the solvents, which resulted in the UV-Vis absorption spectra differences. The comparison of wavelength and of the energy gap in this discussion is listed in Table 1.

Figure 7 Schematic of the electronic structure of C60 as calculated by the Hückel model [80, 81] and its possible electronic excitation transitions experimentally observed in this study. The electronic excitation and emission transitions were numbered in the bracket as (1) to (5) and (6) to (7), respectively.
Figure 7

Schematic of the electronic structure of C60 as calculated by the Hückel model [80, 81] and its possible electronic excitation transitions experimentally observed in this study. The electronic excitation and emission transitions were numbered in the bracket as (1) to (5) and (6) to (7), respectively.

The schematic electronic transitions and their summaries are presented in Figure 7 and Table 1, respectively. The possible HOMO-LUMO gap of the solid C60 was obtained at 1.69 eV. This value was 10% to 15% smaller than the band gap energy of the C60 solution, which was 1.99 eV (this was also in agreement with previous results) [81]. Experimentally, five possible excitation transitions existed, as illustrated in Figure 7 by arrows (1) to (5) (i.e., Hu → T1u, Hu → T1g, Hu → Hg, Hg → T1u, and Hg → T1g, respectively). The excitation transition of Hu → T1u and Hg → T1u might have corresponded to different energies because of the HT and JT active modes. HT modes induced vibronic transition at Hu and Hg orbitals, and the JT distortion effect possibly occurred to the T1u orbital [26, 82, 83].

Following the study of the absorption spectra, the PL spectra were then measured. The PL spectra of the solvents and the dissolved C60 in each of the solvents are shown as red and blue dashed lines, respectively, in Figure 8(a) to (c). As seen in the generated spectra, the PL intensity of C60 in xylene was higher than in other solvents, which might have corresponded to its higher solubility, as discussed earlier. The PL band characteristic of C60 in xylene was similar to that of C60 in toluene. Meanwhile, the emission generated by the C60 dissolved in TCE was far less intense than that of the other solvents.

Figure 8 The PL spectra of C60 in the different solvents of (a) toluene, (b) xylene, and (c) TCE; (d) the compilation of PL spectra after being subtracted and (e-f) their emphasized regions.
Figure 8

The PL spectra of C60 in the different solvents of (a) toluene, (b) xylene, and (c) TCE; (d) the compilation of PL spectra after being subtracted and (e-f) their emphasized regions.

The PL spectra of the C60 solution consisted of the PL of interacted C60 and the solvents used in each C60 solution, as shown in Figure 8. The solvent used may have interfered with the original PL of C60. Each of the solvents had their own characteristic PL, as shown in Figure 8(a) to (c) in blue dashed lines that represent toluene, xylene, and TCE, respectively. For example, in the 600 to 900 nm region, toluene had a PL that coincided with the subtracted PL of C60, but at different intensities. On the other hand, xylene and TCE had different PL characteristics at 650 to 750 nm and 400 to 700 nm, respectively. Thus, the PL profile of the C60 solution could have been superimposed with PL from the solvents. Therefore, to identify the emission profile spectra of the interacted C60, the PL spectra of the dissolved C60 were subtracted by the PL spectra of the solvents alone. The results of the subtracted spectra are shown as solid black lines in Figure 8(a) to (c). The comparison and normalization of the C60 solution were finally given to the spectra divided by the max intensity, as shown in Figure 8(d) to (f).

After being subtracted, the PL spectra of the C60 solution in toluene and xylene revealed emissions on the longer wavelength region than the excitation wavelength (i.e., >420 nm region), as presented in Figure 8(d). As seen in Figure 8(a) to (f), the spectra of C60 in the TCE solvent indicated a difference compared to the other solvents. Unlike the C60 solution in toluene and xylene, the C60 in TCE revealed no emission in the 430 to 470 nm region. This phenomenon might have been relevant to the solubility of C60 in TCE. The solubility of C60 in TCE was lower than in the other two solvents, allowing the resulting spectra to have lower intensity and a different emission wavelength. The toluene and xylene solvents had a similar structure, in which they had a benzene ring attached by one and two methyl groups, respectively. Therefore, because the chemical structure was not significantly different, the interaction between fullerenes and toluene or xylene molecules was similar.

The experimental fluorescence features of C60 in toluene or xylene in the wavelength of 430 to 900 nm, as shown in both of Figure 8(e) to (f), were almost the same with the C60 fluorescence spectra in benzene and toluene reported in pioneering studies. Zhang et al. reported an intense emission peak at 440 nm and a broad peak in the region of 600 to 800 nm [23, 66]. The broad emission in the region of 600 to 800 nm was also reported by Palewska et al. [70] and Zhao et al. [84]. They also confirmed that C60 fluorescence in different solvents, such as benzene, toluene, n-hexane, CS2, and DMSO, reveals different features [70, 84]. However, the fluorescence of C60 in TCE has not been reported elsewhere.

The PL transitions possessed by the C60 solution after the subtraction are listed in Table 2. The presented PL band data were obtained from the normalized data of the subtracted spectra of C60 solutions and the solvents in nm and were converted to band energies in eV. P1 to P4 and P5 (P5’) to P6 (P6’) are identified as Hg ← T1u and Hu ← T1u emission transitions, respectively. In these transitions, the HT and JT effect might have caused vibronic transitions, as discussed earlier, thus revealing the different emission band energies.

Table 2

The emission bands of C60 in different solvents after subtraction.

Emission electronic transitionsPL (emission) bands#
C60 in tolueneC60 in xyleneC60 in TCE
nmeVnmeVnmeV
*(6): Hu ← T1uP5697.201.78697.201.78--
P5’----720.461.72
P6735.631.69735.631.69--
P6’----750.771.65
*(7): Hg ← T1uP1432.742.87431.822.88438.77 (sh)2.83 (sh)
P2440.622.82439.702.82--
P3443.872.80443.402.80--
P4460.982.69460.522.70--

  1. Note: # The data were taken from Figure 8; (6) to (7) correspond to the purple downward arrows in Figure 7; * JT and HT effects possibly occurred; sh = shoulder.

According to the recorded phenomena, the illustration of the solvent effect on the fluorescence emission of C60 is shown in Figure 9. At first, when C60 was surrounded with the solvent molecules, the dipole moments of the solvent molecules could interact with the dipole moment of C60 to yield an ordered distribution of solvent molecules around C60. In the case of a non-polar solvent with no dipole moment, the fluorophore (C60) was not affected. Therefore, when the solvent molecules surrounded C60, the solvent dipole moments interacted with the dipole moments of C 60 to align the solvent dipoles with the C60 dipoles.

Figure 9 The illustration of the solvent effect to fluorescence emission of C60 in different solvents: (a) toluene or xylene, and (b) TCE. S0, S 1, and S1’ were notable for the ground state and excited state of C60 and the excited state of the solvent. The number indicates the excitation and emission sequence steps as follows: 1, excitation; 2, vibrational relaxation; 3 and 4, solvent relaxation; 5, fluorescence; and 6, vibrational relaxation.
Figure 9

The illustration of the solvent effect to fluorescence emission of C60 in different solvents: (a) toluene or xylene, and (b) TCE. S0, S 1, and S1’ were notable for the ground state and excited state of C60 and the excited state of the solvent. The number indicates the excitation and emission sequence steps as follows: 1, excitation; 2, vibrational relaxation; 3 and 4, solvent relaxation; 5, fluorescence; and 6, vibrational relaxation.

As illustrated in Figure 9, after C60 was excited from the ground state (S0) to the higher vibrational levels of the first excited singlet state (S1; Step 1), the excited C60 and solvent dipoles became unaligned. At the excited state, the excess vibrational energy was rapidly lost to surrounding solvent molecules as C60 slowly relaxed to the lowest vibrational energy level of the solvent excited state (S1,)namely the vibrational and solvent relaxation with no radiation (Steps 2 to 4). In the latter step, the dipole moments were re-aligned. Furthermore, when C60 lay in the lowest energy level of the solvent excited state, it returned to the ground state of C60. As shown in Figure 9, the more polar solvents produced a narrower emission gap; that is, a bathochromic/red-shift (shifting to longer wavelength) was obtained. This hypothesis agreed with the data shown in Table 2, which shows that the emission bands of the C60 solution in TCE commonly shifted to the higher wavelength. However, considering the dipole moments of the three solvents was only slightly different (compared to another polar solvent such water, which has a dipole moment of 1.87 D [64]); the reduction of the emission band was not large.

Theoretically, excitation occurs at shorter wavelengths or higher energy than the emission process. Conversely, emission generally appears at a longer wavelength than excitation. Moreover, both excitation and emission often appear to have a symmetric characteristic (mirror image rule) in which the distance between their two peaks is known as a stoke shift [18]. Therefore, the excitation and emissions spectra possessed by the C60 solutions in different solvents were combined, as shown in Figure 10. Two PL phenomena observed at wavelengths 430 to 470 nm and 650 to 850 nm were then confirmed to their absorption spectra.

Figure 10 The excitation and emission of C60 solution in different solvents at the wavelength range of: (a) 350 to 490 nm and (b) 450 to 850 nm.
Figure 10

The excitation and emission of C60 solution in different solvents at the wavelength range of: (a) 350 to 490 nm and (b) 450 to 850 nm.

As seen in Figure 10(a), the emission possessed by the C60 solutions in toluene and xylene at the wavelength of 420 to 480 nm had a symmetric characteristic with the excitation at wavelengths of 380 to 420 nm. The results of PL emissions were observable at wavelengths of 430 nm as a result of the electron transition of So ← S1 (Ag ← T1u). The absorption spectra of the C60 solution in TCE are shown in a solid blue line in Figure 10(a); these spectra had a very large signal to noise (S/N) ratio. This excitation was possible due to the π → π* transition. The π → π* transition in C60 solution in TCE was weaker than that of the toluene and xylene solutions due to the absence of the benzene ring in TCE. Thus, the PL intensity of the C60 solution in TCE weakened due to its lower solubility, as discussed previously. The absence of a PL peak at ~430 nm has also been reported for C60 in DMSO [66], which does not have a carbon hexagonal ring in its structure.

Unlike the phenomenon shown in Figure 10(a), in which the C60 solution in TCE had weak PL, the wider wavelength region in Figure 10(b) shows that the C60 solution in all three solvents had a significant PL peak that was well-observed. In Figure 10(b), the absorption (excitation) bands located at 450 to 650 nm had a mirror image with the emission bands located at 650 to 850 nm. However, the original emission intensity of the C60 solution in TCE before spectra normalization was considerably less, as shown in the original spectra in Figure 8(c) to (d). As discussed earlier, the excitation mechanism was predominantly derived from the solvents. The solvatochromism of C60, which is a non-polar solute in non-polar solvents such as toluene and xylene, is commonly known to be solely dependent on dispersion forces influenced by the solvents’ polarity, as indicated from their dipole moment. TCE had slightly higher dipole moments; that is, the emission band in TCE shifted to the longer wavelength, which is shown in Figure 8(f) and Figure 10(b). The C60 in toluene and xylene had almost closed emission bands at around 697 and 735 nm, labeled as P5 to P6 in Figure 8(f), respectively; however, the C60 in TCE had a shifted emission peak at 720 and 750 nm, labeled as P5’ and P6’ in Figure 8(f), respectively.

Correspondingly, PL spectroscopy has been found to better distinguish possible interactions between C60 and organic solvents with their different polarities than UV absorbance spectroscopy. The C60 showed a significantly different emission peak when it interacted with TCE, the more polar of the non-polar solvents used in this study.

4 Conclusion

The solid C60 had different optical absorption characteristics compared to that of the dissolved C60 in organic solvents. The C60 solution in toluene, xylene, and TCE solvents generated excitation peaks at 404, 535, 570, 591, and 625 nm, which were slightly different from the excitation band energies of the solid C60, as estimated by the Kubelka-Munk band gap calculations. Because of the higher solvent polarity of TCE, the C60 solution in TCE revealed a red-shift in which the PL emission peaks shifted to longer wavelengths as compared to C60 in toluene and xylene. The PL characteristics studied by spectroscopy better distinguished possible interactions between the C60 and organic solvents, with their different polarities, than did the characteristics studied by UV-Vis absorbance spectroscopy. Therefore, in future applications, due to its unique characteristics as an environment-sensitive fluorophore, C60 could be employed as a fluorescent probe to detect the solvent polarity effects, molecular associations, and complex formation with polar and non-polar small molecules and macromolecules.

Acknowledgments

This work was partly supported by Grants-in-Aid Research of the Ministry of Research, Technology and Higher Education under project no. 543/UN27.21/PP/2018, 474/UN27.21/PP/2018, and 719/UN27.21/PN/2019. The authors also would like to deliver their gratitude to the Laser Research Group, RCP-IIS for their hosting thus this research can be conducted, and especially to Mrs. F. Destyorini, M.Si. and Dr. T. Sudiro for their support in providing research materials of xylene and toluene, respectively.

  1. Conflict of interest: Authors declare no conflict of interest. The authors confirm that T E Saraswati and Y Herbani are the main contributors for the project.

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Received: 2018-09-30
Accepted: 2019-05-23
Published Online: 2019-12-31

© 2019 Teguh Endah Saraswati et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 Public License.

Articles in the same Issue

  1. Regular Articles
  2. Research on correlation of compositions with oestrogenic activity of Cistanche based on LC/Q-TOF-MS/MS technology
  3. Efficacy of Pyrus elaeagnifolia subsp. elaeagnifolia in acetic acid–induced colitis model
  4. Anti-inflammatory and antinociceptive features of Bryonia alba L.: As a possible alternative in treating rheumatism
  5. High efficiency liposome fusion induced by reducing undesired membrane peptides interaction
  6. Prediction of the Blood-Brain Barrier Permeability Using RP-18 Thin Layer Chromatography
  7. Phytic Acid Extracted from Rice Bran as a Growth Promoter for Euglena gracilis
  8. Development of a validated spectrofluorimetric method for assay of sotalol hydrochloride in tablets and human plasma: application for stability-indicating studies
  9. Topological Indices of Hyaluronic Acid-Paclitaxel Conjugates’ Molecular Structure in Cancer Treatment
  10. Thermodynamic properties of the bubble growth process in a pool boiling of water-ethanol mixture two-component system
  11. Critical Roles of the PI3K-Akt-mTOR Signaling Pathway in Apoptosis and Autophagy of Astrocytes Induced by Methamphetamine
  12. Characteristics of Stable Hydrogen and Oxygen Isotopes of Soil Moisture under Different Land Use in Dry Hot Valley of Yuanmou
  13. Specific, highly sensitive and simple spectrofluorimetric method for quantification of daclatasvir in HCV human plasma patients and in tablets dosage form
  14. Chromium-modified cobalt molybdenum nitrides as catalysts for ammonia synthesis
  15. Langerhans cell-like dendritic cells treated with ginsenoside Rh2 regulate the differentiation of Th1 and Th2 cells in vivo
  16. Identification of Powdery Mildew Blumeria graminis f. sp. tritici Resistance Genes in Selected Wheat Varieties and Development of Multiplex PCR
  17. Computational Analysis of new Degree-based descriptors of oxide networks
  18. The Use Of Chemical Composition And Additives To Classify Petrol And Diesel Using Gas Chromatography–Mass Spectrometry And Chemometric Analysis: A Uk Study
  19. Minimal Energy Tree with 4 Branched Vertices
  20. Jatropha seed oil derived poly(esteramide-urethane)/ fumed silica nanocomposite coatings for corrosion protection
  21. Calculating topological indices of certain OTIS interconnection networks
  22. Energy storage analysis of R125 in UIO-66 and MOF-5 nanoparticles: A molecular simulation study
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  27. Phytochemical screening and estrogenic activity of total glycosides of Cistanche deserticola
  28. Biological evaluation of a series of benzothiazole derivatives as mosquitocidal agents
  29. Chemical pretreatments of Trapa bispinosa's peel (TBP) biosorbent to enhance adsorption capacity for Pb(ll)
  30. Dynamic Changes in MMP1 and TIMP1 in the Antifibrotic Process of Dahuang Zhechong Pill in Rats with Liver Fibrosis
  31. The Optimization and Production of Ginkgolide B Lipid Microemulsion
  32. Photodynamic Therapy Enhanced the Antitumor Effects of Berberine on HeLa Cells
  33. Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
  34. Correlation of Water Fluoride with Body Fluids, Dental Fluorosis and FT4, FT3 –TSH Disruption among Children in an Endemic Fluorosis area in Pakistan
  35. A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  36. Free Radical Scavenging Activity of Essential Oil of Eugenia caryophylata from Amboina Island and Derivatives of Eugenol
  37. Effects of Blue and Red Light On Growth And Nitrate Metabolism In Pakchoi
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  39. Solar photodegradation of carbamazepine from aqueous solutions using a compound parabolic concentrator equipped with a sun tracking system
  40. Influence of sub-inhibitory concentration of selected plant essential oils on the physical and biochemical properties of Pseudomonas orientalis
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  44. Analysis and Biological Evaluation of Arisaema Amuremse Maxim Essential Oil
  45. A preliminary assessment of potential ecological risk and soil contamination by heavy metals around a cement factory, western Saudi Arabia
  46. Anti- inflammatory effect of Prunus tomentosa Thunb total flavones in LPS-induced RAW264.7 cells
  47. Collaborative Influence of Elevated CO2 Concentration and High Temperature on Potato Biomass Accumulation and Characteristics
  48. Methods of extraction, physicochemical properties of alginates and their applications in biomedical field – a review
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  53. Comparative study on the antioxidant activities of ten common flower teas from China
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  57. Silver nanoparticles enhanced fluorescence for sensitive determination of fluoroquinolones in water solutions
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https://doi.org/10.1515/chem-2019-0117
Keywords for this article
C60; UV-Vis absorption; photoluminescence; solvatochromism; solvent polarity
Creative Commons
BY 4.0

Articles in the same Issue

  1. Regular Articles
  2. Research on correlation of compositions with oestrogenic activity of Cistanche based on LC/Q-TOF-MS/MS technology
  3. Efficacy of Pyrus elaeagnifolia subsp. elaeagnifolia in acetic acid–induced colitis model
  4. Anti-inflammatory and antinociceptive features of Bryonia alba L.: As a possible alternative in treating rheumatism
  5. High efficiency liposome fusion induced by reducing undesired membrane peptides interaction
  6. Prediction of the Blood-Brain Barrier Permeability Using RP-18 Thin Layer Chromatography
  7. Phytic Acid Extracted from Rice Bran as a Growth Promoter for Euglena gracilis
  8. Development of a validated spectrofluorimetric method for assay of sotalol hydrochloride in tablets and human plasma: application for stability-indicating studies
  9. Topological Indices of Hyaluronic Acid-Paclitaxel Conjugates’ Molecular Structure in Cancer Treatment
  10. Thermodynamic properties of the bubble growth process in a pool boiling of water-ethanol mixture two-component system
  11. Critical Roles of the PI3K-Akt-mTOR Signaling Pathway in Apoptosis and Autophagy of Astrocytes Induced by Methamphetamine
  12. Characteristics of Stable Hydrogen and Oxygen Isotopes of Soil Moisture under Different Land Use in Dry Hot Valley of Yuanmou
  13. Specific, highly sensitive and simple spectrofluorimetric method for quantification of daclatasvir in HCV human plasma patients and in tablets dosage form
  14. Chromium-modified cobalt molybdenum nitrides as catalysts for ammonia synthesis
  15. Langerhans cell-like dendritic cells treated with ginsenoside Rh2 regulate the differentiation of Th1 and Th2 cells in vivo
  16. Identification of Powdery Mildew Blumeria graminis f. sp. tritici Resistance Genes in Selected Wheat Varieties and Development of Multiplex PCR
  17. Computational Analysis of new Degree-based descriptors of oxide networks
  18. The Use Of Chemical Composition And Additives To Classify Petrol And Diesel Using Gas Chromatography–Mass Spectrometry And Chemometric Analysis: A Uk Study
  19. Minimal Energy Tree with 4 Branched Vertices
  20. Jatropha seed oil derived poly(esteramide-urethane)/ fumed silica nanocomposite coatings for corrosion protection
  21. Calculating topological indices of certain OTIS interconnection networks
  22. Energy storage analysis of R125 in UIO-66 and MOF-5 nanoparticles: A molecular simulation study
  23. Velvet Antler compounds targeting major cell signaling pathways in osteosarcoma - a new insight into mediating the process of invasion and metastasis in OS
  24. Effects of Azadirachta Indica Leaf Extract, Capping Agents, on the Synthesis of Pure And Cu Doped ZnO-Nanoparticles: A Green Approach and Microbial Activity
  25. Aqueous Micro-hydration of Na+(H2O)n=1-7 Clusters: DFT Study
  26. A proposed image-based detection of methamidophos pesticide using peroxyoxalate chemiluminescence system
  27. Phytochemical screening and estrogenic activity of total glycosides of Cistanche deserticola
  28. Biological evaluation of a series of benzothiazole derivatives as mosquitocidal agents
  29. Chemical pretreatments of Trapa bispinosa's peel (TBP) biosorbent to enhance adsorption capacity for Pb(ll)
  30. Dynamic Changes in MMP1 and TIMP1 in the Antifibrotic Process of Dahuang Zhechong Pill in Rats with Liver Fibrosis
  31. The Optimization and Production of Ginkgolide B Lipid Microemulsion
  32. Photodynamic Therapy Enhanced the Antitumor Effects of Berberine on HeLa Cells
  33. Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
  34. Correlation of Water Fluoride with Body Fluids, Dental Fluorosis and FT4, FT3 –TSH Disruption among Children in an Endemic Fluorosis area in Pakistan
  35. A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  36. Free Radical Scavenging Activity of Essential Oil of Eugenia caryophylata from Amboina Island and Derivatives of Eugenol
  37. Effects of Blue and Red Light On Growth And Nitrate Metabolism In Pakchoi
  38. miRNA-199a-5p functions as a tumor suppressor in prolactinomas
  39. Solar photodegradation of carbamazepine from aqueous solutions using a compound parabolic concentrator equipped with a sun tracking system
  40. Influence of sub-inhibitory concentration of selected plant essential oils on the physical and biochemical properties of Pseudomonas orientalis
  41. Preparation and spectroscopic studies of Fe(II), Ru(II), Pd(II) and Zn(II) complexes of Schiff base containing terephthalaldehyde and their transfer hydrogenation and Suzuki-Miyaura coupling reaction
  42. Complex formation in a liquid-liquid extraction-chromogenic system for vanadium(IV)
  43. Synthesis, characterization (IR, 1H, 13C & 31P NMR), fungicidal, herbicidal and molecular docking evaluation of steroid phosphorus compounds
  44. Analysis and Biological Evaluation of Arisaema Amuremse Maxim Essential Oil
  45. A preliminary assessment of potential ecological risk and soil contamination by heavy metals around a cement factory, western Saudi Arabia
  46. Anti- inflammatory effect of Prunus tomentosa Thunb total flavones in LPS-induced RAW264.7 cells
  47. Collaborative Influence of Elevated CO2 Concentration and High Temperature on Potato Biomass Accumulation and Characteristics
  48. Methods of extraction, physicochemical properties of alginates and their applications in biomedical field – a review
  49. Characteristics of liposomes derived from egg yolk
  50. Preparation of ternary ZnO/Ag/cellulose and its enhanced photocatalytic degradation property on phenol and benzene in VOCs
  51. Influence of Human Serum Albumin Glycation on the Binding Affinities for Natural Flavonoids
  52. Synthesis and antioxidant activity of 2-methylthio-pyrido[3,2-e][1,2,4] triazolo[1,5-a]pyrimidines
  53. Comparative study on the antioxidant activities of ten common flower teas from China
  54. Molecular Properties of Symmetrical Networks Using Topological Polynomials
  55. Synthesis of Co3O4 Nano Aggregates by Co-precipitation Method and its Catalytic and Fuel Additive Applications
  56. Phytochemical analysis, Antioxidant and Antiprotoscolices potential of ethanol extracts of selected plants species against Echinococcus granulosus: In-vitro study
  57. Silver nanoparticles enhanced fluorescence for sensitive determination of fluoroquinolones in water solutions
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  62. Novel 1,8-Naphthyridine Derivatives: Design, Synthesis and in vitro screening of their cytotoxic activity against MCF7 cell line
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  69. The anti-corrosion behaviour of Satureja montana L. extract on iron in NaCl solution
  70. Interleukin-4, hemopexin, and lipoprotein-associated phospholipase A2 are significantly increased in patients with unstable carotid plaque
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  74. Kinetics of Iron Removal From Ti-Extraction Blast Furnace Slag by Chlorination Calcination
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  76. Exploring the optoelectronic properties of a chromene-appended pyrimidone derivative for photovoltaic applications
  77. Effect of He Qi San on DNA Methylation in Type 2 Diabetes Mellitus Patients with Phlegm-blood Stasis Syndrome
  78. Cyclodextrin potentiometric sensors based on selective recognition sites for procainamide: Comparative and theoretical study
  79. Greener synthesis of dimethyl carbonate from carbon dioxide and methanol using a tunable ionic liquid catalyst
  80. Nonisothermal Cold Crystallization Kinetics of Poly(lactic acid)/Bacterial Poly(hydroxyoctanoate) (PHO)/Talc
  81. Enhanced adsorption of sulfonamide antibiotics in water by modified biochar derived from bagasse
  82. Study on the Mechanism of Shugan Xiaozhi Fang on Cells with Non-alcoholic Fatty Liver Disease
  83. Comparative Effects of Salt and Alkali Stress on Antioxidant System in Cotton (Gossypium Hirsutum L.) Leaves
  84. Optimization of chromatographic systems for analysis of selected psychotropic drugs and their metabolites in serum and saliva by HPLC in order to monitor therapeutic drugs
  85. Electrocatalytic Properties of Ni-Doped BaFe12O19 for Oxygen Evolution in Alkaline Solution
  86. Study on the removal of high contents of ammonium from piggery wastewater by clinoptilolite and the corresponding mechanisms
  87. Phytochemistry and toxicological assessment of Bryonia dioica roots used in north-African alternative medicine
  88. The essential oil composition of selected Hemerocallis cultivars and their biological activity
  89. Mechanical Properties of Carbon Fiber Reinforced Nanocrystalline Nickel Composite Electroforming Deposit
  90. Anti-c-myc efficacy block EGFL7 induced prolactinoma tumorigenesis
  91. Topical Issue on Applications of Mathematics in Chemistry
  92. Zagreb Connection Number Index of Nanotubes and Regular Hexagonal Lattice
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  94. Valency-based molecular descriptors of Bakelite network BNmn
  95. Computing Topological Indices for Para-Line Graphs of Anthracene
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  97. Topological Descriptor of 2-Dimensional Silicon Carbons and Their Applications
  98. Topological invariants for the line graphs of some classes of graphs
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  100. Generators of Maximal Subgroups of Harada-Norton and some Linear Groups
  101. Special Issue on POKOCHA 2018
  102. Influence of Production Parameters on the Content of Polyphenolic Compounds in Extruded Porridge Enriched with Chokeberry Fruit (Aronia melanocarpa (Michx.) Elliott)
  103. Effects of Supercritical Carbon Dioxide Extraction (SC-CO2) on the content of tiliroside in the extracts from Tilia L. flowers
  104. Impact of xanthan gum addition on phenolic acids composition and selected properties of new gluten-free maize-field bean pasta
  105. Impact of storage temperature and time on Moldavian dragonhead oil – spectroscopic and chemometric analysis
  106. The effect of selected substances on the stability of standard solutions in voltammetric analysis of ascorbic acid in fruit juices
  107. Determination of the content of Pb, Cd, Cu, Zn in dairy products from various regions of Poland
  108. Special Issue on IC3PE 2018 Conference
  109. The Photocatalytic Activity of Zns-TiO2 on a Carbon Fiber Prepared by Chemical Bath Deposition
  110. N-octyl chitosan derivatives as amphiphilic carrier agents for herbicide formulations
  111. Kinetics and Mechanistic Study of Hydrolysis of Adenosine Monophosphate Disodium Salt (AMPNa2) in Acidic and Alkaline Media
  112. Antimalarial Activity of Andrographis Paniculata Ness‘s N-hexane Extract and Its Major Compounds
  113. Special Issue on ABB2018 Conference
  114. Special Issue on ICCESEN 2017
  115. Theoretical Diagnostics of Second and Third-order Hyperpolarizabilities of Several Acid Derivatives
  116. Determination of Gamma Rays Efficiency Against Rhizoctonia solani in Potatoes
  117. Studies On Compatibilization Of Recycled Polyethylene/Thermoplastic Starch Blends By Using Different Compatibilizer
  118. Liquid−Liquid Extraction of Linalool from Methyl Eugenol with 1-Ethyl-3-methylimidazolium Hydrogen Sulfate [EMIM][HSO4] Ionic Liquid
  119. Synthesis of Graphene Oxide Through Ultrasonic Assisted Electrochemical Exfoliation
  120. Special Issue on ISCMP 2018
  121. Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells
  122. The influence of the grafted aryl groups on the solvation properties of the graphyne and graphdiyne - a MD study
  123. Electrochemical modification of platinum and glassy carbon surfaces with pyridine layers and their use as complexing agents for copper (II) ions
  124. Effect of Electrospinning Process on Total Antioxidant Activity of Electrospun Nanofibers Containing Grape Seed Extract
  125. Effect Of Thermal Treatment Of Trepel At Temperature Range 800-1200˚C
  126. Topical Issue on Agriculture
  127. The effect of Cladophora glomerata exudates on the amino acid composition of Cladophora fracta and Rhizoclonium sp.
  128. Influence of the Static Magnetic Field and Algal Extract on the Germination of Soybean Seeds
  129. The use of UV-induced fluorescence for the assessment of homogeneity of granular mixtures
  130. The use of microorganisms as bio-fertilizers in the cultivation of white lupine
  131. Lyophilized apples on flax oil and ethyl esters of flax oil - stability and antioxidant evaluation
  132. Production of phosphorus biofertilizer based on the renewable materials in large laboratory scale
  133. Human health risk assessment of potential toxic elements in paddy soil and rice (Oryza sativa) from Ugbawka fields, Enugu, Nigeria
  134. Recovery of phosphates(V) from wastewaters of different chemical composition
  135. Special Issue on the 4th Green Chemistry 2018
  136. Dead zone for hydrogenation of propylene reaction carried out on commercial catalyst pellets
  137. Improved thermally stable oligoetherols from 6-aminouracil, ethylene carbonate and boric acid
  138. The role of a chemical loop in removal of hazardous contaminants from coke oven wastewater during its treatment
  139. Combating paraben pollution in surface waters with a variety of photocatalyzed systems: Looking for the most efficient technology
  140. Special Issue on Chemistry Today for Tomorrow 2019
  141. Applying Discriminant and Cluster Analyses to Separate Allergenic from Non-allergenic Proteins
  142. Chemometric Expertise Of Clinical Monitoring Data Of Prolactinoma Patients
  143. Chemomertic Risk Assessment of Soil Pollution
  144. New composite sorbent for speciation analysis of soluble chromium in textiles
  145. Photocatalytic activity of NiFe2O4 and Zn0.5Ni0.5Fe2O4 modified by Eu(III) and Tb(III) for decomposition of Malachite Green
  146. Photophysical and antibacterial activity of light-activated quaternary eosin Y
  147. Spectral properties and biological activity of La(III) and Nd(III) Monensinates
  148. Special Issue on Monitoring, Risk Assessment and Sustainable Management for the Exposure to Environmental Toxins
  149. Soil organic carbon mineralization in relation to microbial dynamics in subtropical red soils dominated by differently sized aggregates
  150. A potential reusable fluorescent aptasensor based on magnetic nanoparticles for ochratoxin A analysis
  151. Special Issue on 13th JCC 2018
  152. Fluorescence study of 5-nitroisatin Schiff base immobilized on SBA-15 for sensing Fe3+
  153. Thermal and Morphology Properties of Cellulose Nanofiber from TEMPO-oxidized Lower part of Empty Fruit Bunches (LEFB)
  154. Encapsulation of Vitamin C in Sesame Liposomes: Computational and Experimental Studies
  155. A comparative study of the utilization of synthetic foaming agent and aluminum powder as pore-forming agents in lightweight geopolymer synthesis
  156. Synthesis of high surface area mesoporous silica SBA-15 by adjusting hydrothermal treatment time and the amount of polyvinyl alcohol
  157. Review of large-pore mesostructured cellular foam (MCF) silica and its applications
  158. Ion Exchange of Benzoate in Ni-Al-Benzoate Layered Double Hydroxide by Amoxicillin
  159. Synthesis And Characterization Of CoMo/Mordenite Catalyst For Hydrotreatment Of Lignin Compound Models
  160. Production of Biodiesel from Nyamplung (Calophyllum inophyllum L.) using Microwave with CaO Catalyst from Eggshell Waste: Optimization of Transesterification Process Parameters
  161. The Study of the Optical Properties of C60 Fullerene in Different Organic Solvents
  162. Composite Material Consisting of HKUST-1 and Indonesian Activated Natural Zeolite and its Application in CO2 Capture
  163. Topical Issue on Environmental Chemistry
  164. Ionic liquids modified cobalt/ZSM-5 as a highly efficient catalyst for enhancing the selectivity towards KA oil in the aerobic oxidation of cyclohexane
  165. Application of Thermal Resistant Gemini Surfactants in Highly Thixotropic Water-in-oil Drilling Fluid System
  166. Screening Study on Rheological Behavior and Phase Transition Point of Polymer-containing Fluids produced under the Oil Freezing Point Temperature
  167. The Chemical Softening Effect and Mechanism of Low Rank Coal Soaked in Alkaline Solution
  168. The Influence Of NO/O2 On The NOx Storage Properties Over A Pt-Ba-Ce/γ-Al2O3 Catalyst
  169. Special Issue on the International conference CosCI 2018
  170. Design of SiO2/TiO2 that Synergistically Increases The Hydrophobicity of Methyltrimethoxysilane Coated Glass
  171. Antidiabetes and Antioxidant agents from Clausena excavata root as medicinal plant of Myanmar
  172. Development of a Gold Immunochromatographic Assay Method Using Candida Biofilm Antigen as a Bioreceptor for Candidiasis in Rats
  173. Special Issue on Applied Biochemistry and Biotechnology 2019
  174. Adsorption of copper ions on Magnolia officinalis residues after solid-phase fermentation with Phanerochaete chrysosporium
  175. Erratum
  176. Erratum to: Sand Dune Characterization For Preparing Metallurgical Grade Silicon
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