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Color tunable benzothiadiazole-based small molecules for lightening applications

  • Nusret Kaya EMAIL logo
Published/Copyright: November 3, 2023
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Open Chemistry
From the journal Open Chemistry Volume 21 Issue 1

Abstract

2,1,3-Benzothiadiazole (BTD) is a key motif for the chemistry of photoluminescence molecules and its application in lightening technology as well as cell imagining. Evaluating the characteristics and reaction mechanisms of the BTD derivatives in molecular is critical for molecular designing. Research has been turned to BTD-extended derivatives owing to their possible usage in organic photovoltaics, organic light-emitting diodes, liquid crystal devices, dye-sensitized solar cells, and many other applications. Herein, three small molecules with a BTD core, 4,7-di-m-tolylbenzo[c][1,2,5]thiadiazole (NK1), 4,7-bis(3,4,5-trifluorophenyl)benzo[c][1,2,5]thiadiazole (NK2), and 4,7-bis(5-(m-tolyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole (NK3), were designed and synthesized and their molecular structures were elucidated. Additionally, their photophysical and electrochemical behaviors as well as the aggregation-induced enhanced emission properties were examined to investigate their possible usage in cell imaging and organic electronic applications. The HOMO energy level of molecules has been found as −5.96, −5.58, and −5.60 eV, respectively. In the emission spectra, it was seen that molecules showed green, blue, and red emission, respectively.

Graphical abstract

Keywords: benzothiadiazole; small organic molecule; molecular characterization; single crystal

1 Introduction

π-Conjugated organic structures have an important place in industrial and academic studies for organic electronic applications like organic light-emitting diodes (OLEDs), thin film organic field-effect transistors, as well as the fluorescence probes, organic solid lasers, and due to their electrochemical and optical characteristics [1,2,3]. Especially in the organic electronic field, molecules containing quinoxaline [4], benzimidazole [5], and 2,1,3-benzothiadiazole (BTD) building blocks have been used as a π-conjugated organic structure [6]. BTD is one of the most crucial classes of conjugated structures due to the relatively higher reduction potentials and electron affinity (EA) required for the usage. In fact, the π-extended conjugated structures’ HOMO/LUMO levels are defined by their electrochemical reduction/oxidation potentials, or their EA and ionization potentials that are strongly related to the energy of the beginning of the absorption peak in the solid phase spectrum [7].

BTD, as an electron-withdrawing acceptor group, has received considerable attention for photovoltaic systems as well as fluorescent sensors, and photocatalytic studies [8]. BTD can be functionalized with various donor groups after the bromination reaction (Figure 1). Thanks to this feature, it has been possible to develop bright molecules with many different purposes.

Figure 1 Structure of BTD (X: functional group).
Figure 1

Structure of BTD (X: functional group).

In 2021, Nie et al. classified small molecules with a BTD core into four groups according to the number of having BTD core and compared their efficiency [9]. The efficiency of the molecules using the BTD motif in organic photovoltaics was compared depending on the functional groups they have. In another study conducted in 2022, the efficacy of functional groups attached to the BTD group in photocatalysis was assessed [10].

Special phenomena termed aggregation-induced emission (AIE) and aggregation-induced enhanced emission (AIEE) occur in molecules that show increased emission intensity at higher concentrations than in dilute solutions [11,12,13]. AIEE active organic compounds can be used as luminescent analytical/biochemical probes, cell imaging, phototherapy, liquid crystals, and organic electronics due to their high emissivity. AIEE active BTD derivatives are limited in the literature. The initial strategy used for the development of AIE-active molecules with a BTD core was to attach the tetraphenylethylene to the BTD core (Figure 2) [14]. In recent years, Pazini et al. have presented a series of BTD-derived molecules, studying the presence of AIEE properties in acetone/water mixture. They presented eight new organic molecules (given in Figure 2) with BTD core and they showed AIEEgenic feature in the high polarity [15]. AIEgenic molecules that contain BTD motifs published to date are presented in Figure 2.

Figure 2 AIEgenic molecules containing BTD motif presented to date.
Figure 2

AIEgenic molecules containing BTD motif presented to date.

One of the biggest problems in developing emissive molecules for OLEDs is the aggregation-inducing quenching effect. This effect is that molecules that show high emissivity in the solution phase do not show emissivity or low emissivity by clustering at the coating stage in device production. In this sense, the obtaining of new organic molecules that can exhibit intense light emission in the solid phase has significance.

It is known that molecules with BTD cores have many applications. Based on this, three molecules that have BTD cores were designed in the study. The trifluoro phenyl group has been attached due to fluorine atom’s strong electron-drawing characteristics which effectively reduce their frontier orbital levels. The methyl phenyl group has been used as an electron-donating group in the NK2 molecule. 2-(m-Tolyl)thiophene group increased conjugation thus it enabled to obtained lower band gap. It was examined how these groups affected the photophysical and electrochemical properties of the molecule, and it was also investigated whether they were AIEgenic in the mixture of acetone/water for possible applications.

2 Results and discussion

2.1 Molecular characterization

The pathways of the synthesis of NK1, NK2, and NK3 molecules are presented in Scheme 1. Synthesis details of NK series molecules and related intermediates are presented in the Supporting Information (SI). The most widely utilized precursor for synthesizing the π-conjugated photoluminescence molecules with a BTD core is Br-BT. Br-TBT was obtained by the bromination of TBT with NBS in THF. TBT was prepared by Stille C–C coupling reaction between Br-BT and (2-thienyl)tributylstannane with a palladium catalyst in a moderate yield. NK1 and NK2 were synthesized by Suzuki C–C coupling reaction between Br-BT and 3-tolylboronic acid or 3,4,5-trifluorophenylboronic acid in the presence of the Pd(PPh3)4 catalyst which is the same procedure in the literature [16]. NK3 was synthesized by Suzuki C–C coupling reaction between Br-TBT and 3-tolylboronic acid. The molecular structures of NK1, NK2, and NK3 were illuminated by 1H NMR and 13C NMR. NMR and the mass spectral data of the final products and intermediates have been presented in SI.

Scheme 1 Synthetic methods of NK1, NK2, and NK3 molecules. (i) HBr/Br2, (ii) 3-tolylboronic acid or 3,4,5-trifluorophenylboronic acid/toluene, K2CO3, 110–120°C, (iii) (2-thienyl)tributylstannane/THF, reflux, (iv) NBS/DMF, r.t., and (v) 3-tolylboronic acid/toluene, K2CO3, 110–120°C.
Scheme 1

Synthetic methods of NK1, NK2, and NK3 molecules. (i) HBr/Br2, (ii) 3-tolylboronic acid or 3,4,5-trifluorophenylboronic acid/toluene, K2CO3, 110–120°C, (iii) (2-thienyl)tributylstannane/THF, reflux, (iv) NBS/DMF, r.t., and (v) 3-tolylboronic acid/toluene, K2CO3, 110–120°C.

As can be seen from the HNMR spectrum of NK1, aromatic protons appear between 7.0 and 7.9 ppm (Figure S4). NK1 has two methyl groups and these six protons appear at 2.52 ppm as a singlet. All integrations are compatible with the calculated proton numbers. NK2 has six aromatic protons. Four protons have the same environment, and other two protons have the same environment, so it is usual to observe just two peaks. The integration of one of them is equal to two and another’s integration is equal to four as expected. For the NK3 molecule, there are two methyl groups, and these six protons appear at 2.45 ppm as a singlet. In the aromatic region, the integration is compatible with the calculated proton numbers. NK3 has 14 aromatic protons. The total integration is equal to 14 as expected. All 13C NMR results are compatible with the obtained structures.

2.2 Confocal Raman microscopy

The Raman spectra of NK1, NK2, and NK3 are presented in Figure 3. The core structures of the molecules were the same for all new molecules which were designed to aim polarity differences and to shift the light absorption bands of molecular structures. Raman bands of compounds seem similar; however, the bonds’ shifts could be observed clearly in their spectra. The main S–N bonds of BTD were observed at 1,000 cm−1. This bond intensity changed with the substituent group’s electron-repelling behavior and affected electron density distribution on the core BTD structure. NK1’s side groups have increased polarity on the S–N bonds and elevated band count rates than NK2 and NK3. Crystalline properties of NK1, NK2, and NK3 might be carried out from the S–N deformation band that was the same as the Br-TBT crystal form. BTD core groups packing into the NK1 crystallinity were higher than NK2 and NK3 crystallinity because of the bandwidth increment. The vibrational polarization bands of aromatic ═C–H bond were seen at around 3,000 cm−1, but it could not be seen because of low count rates and low polarities than to the other molecular bonds due to spectrums focused on between 1,750 and 100 cm−1 [17]. The attaching of a substituent to a molecule inversely affects the intensities of these bands. The increase of substituents in the aromatic ring decreases the intensity of C−H bonds. Whereas the bands of –C═C– aromatic bonds were seen at 1,556, 1,552, and 1,543 cm−1, the asymmetric vibration bands of –C═N– were noticed at 1,355, 1,371, and 1,368 cm−1 for NK1, NK2, and NK3, respectively [18] which is related to benzothiazole moiety [19,20]. The C–S bonds appear in the range 570–720 cm−1 in the Raman spectrum [21]. C–S bonds in NK3 molecule were seen at 621 cm−1. The deformation of Ph-F bands was observed at 995 cm−1 for the NK1 molecule.

Figure 3 The Raman spectra of NK1, NK2, and NK3 molecules.
Figure 3

The Raman spectra of NK1, NK2, and NK3 molecules.

2.3 Photophysical and electrochemical characteristics

The absorption characteristics of the compounds were measured in 10−5 M CHCl3 solution and given in Figure 4. In the spectra of the compounds, the π/π* transition bands correspond to higher energy regions seen at 272, 270, and 339 nm for NK1, NK2, and NK3, respectively. The lower energy absorption band that was seen at 383, 381, and 485 nm may correspond to intramolecular charge transfer (ICT). The red-shifted (⁓30 nm) maxima of NK3 compared to NK1 and NK2 are related to increased conjugation thanks to the two thiophene rings. The determination of the characteristic features of these types of molecules, such as energy gap and optical and electrochemical band gap, is important for photovoltaic applications. The most common approach for the identification of optical band gap (E opt g) is to define the wavelength corresponding to the onset value of the maximum absorption peak. The absorption onset of molecules appears at 432, 449, and 568 nm, respectively. According to this approach, the E g opt of NK1, NK2, and NK3 were determined to be 2.87, 2.76, and 2.18 eV, respectively.

Figure 4 Absorption spectra of NK1, NK2, and NK3 molecules in CHCl3.
Figure 4

Absorption spectra of NK1, NK2, and NK3 molecules in CHCl3.

The fluorescence spectra of the molecules were done in different solvents for the investigation of the solvacromism effect and given in Figure 5. The emission maxima of the molecules were seen at 492, 480, and 614 nm in CHCl3, respectively.

Figure 5 The fluorescence spectra of NK1 (a), NK2 (b), and NK3 (c) molecules in solvents of different polarity.
Figure 5

The fluorescence spectra of NK1 (a), NK2 (b), and NK3 (c) molecules in solvents of different polarity.

The emission maxima of the NK1, NK2, and NK3 are red-shifted (⁓9 nm) as polarity increases. It is possible to indicate that a molecule has solvachromism by increasing the HOMO/LUMO energy gap (λ max) due to increasing solvent polarity. To put it differently, the excited state could be stabilized by the polar solvents than the ground state, resulting in the transition energies (redshift) decrease in such solvents. In general, increasing the solvent polarity leads to an increase in both the emission band and the Stoke shift, indicating a rise in the dipole moment on excitation [22]. The photophysical features of the molecules are summarized in the Table 1. The fluorescence lifetimes of the molecules found 15.00, 12.10, and 12.00 ns in CHCl3 from the time-resolved fluorescence decays (presented in SI). A molecule’s or material’s photoluminescence quantum yield (PLQY) is defined as the number of photons emitted as a proportion of the number of photons absorbed. It is a crucial measurement of luminescent materials. The PLQYs of the NK1, NK2, and NK3 molecules in the solution phase were measured as 96.38, 83.96, and 66.62%, respectively (Figures S16–S18). For NK1, the existence of methyl substituent could hinder the π–π interactions due to a more distorted spatial arrangement and decrease the non-radiative transition. This situation might lead to obtaining the highest PLQY (Φ PL ≈ 96%) value in the NK series molecules. Film phase PLQY has also been measured and found as 68.6, 36.5, and 32.3%, respectively (Figures S19–S21). It can be said that the reason the PLQY of the films is lower than the solution ones is the aggregation that occurs in the film phase. Aggregation caused quenching, resulting in a decrease in quantum yields.

Table 1

Photophysical features of NK1, NK2, and NK3 molecules

Absorption (nm) Emission (nm) PLQY (%)
CHCl3 Toluene THF Acetone CHCl3 ACN in CHCl3* Film phase
NK1 308, 446 484 491 491 492 493 96.38 68.6
NK2 318, 458 485 488 492 492 494 83.96 36.5
NK3 339, 487 606 604 610 608 609 66.62 32.3

*PLQY (%) measurements were performed in CHCl3 with an absorption value of 0.1 A.

Electrochemical characteristics of the molecules were done by cyclic voltammetry (CV) in acetonitrile and resulting voltammograms are given in Figure 6. The oxidation potential (E ox) onset of the molecules was observed at 1.56 eV for NK1. For NK2 and NK3, two oxidation peaks were observed and corresponding to the onset values of these peaks evaluated as 1.18 and 1.49 for NK2 and 1.20 and 1.46 eV for NK3 molecule. Fluorine substitution on any compound is known to decrease the band gap by synergistic HOMO and LUMO stabilization [23]. As expected, it is seen that the band gap decreases with fluorine substitution with the addition of fluorine atoms. The HOMO energy levels of the molecules were determined from the onset values of the reduction potentials (E red) by using the equation HOMO = −(E ox +4.4) eV [24]. HOMO values were calculated and found as −5.96, −5.58, and −5.60 eV, respectively.

Figure 6 Cyclic voltammogram of NK1 (a), NK2 (b), and NK3 (c) molecules.
Figure 6

Cyclic voltammogram of NK1 (a), NK2 (b), and NK3 (c) molecules.

The reduction potential onset of the NK3 exhibited at −0.97 V, corresponding to a LUMO energy level of −3.43 eV for NK3. The electrochemical band gap of NK3 was found as 2.17 eV and this value is compatible with its optical band gap value (2.18 eV). The onset E ox and E red were determined from the voltammograms of the molecules and given in Table 2. LUMO energy level of NK1 and NK2 has been determined by using the optical band gap. For the optical band gap calculation, the following equation was used.

E g opt = 1 , 241 λ ( nm ) .

Table 2

Electrochemical properties of NK1, NK2, and NK3 molecules

HOMO(eV) LUMO(eV) E ox(eV) E red(eV) Optical band gap (eV)
NK1 −5.96 −3.09* 1.56 — 2.87
NK2 −5.58 −2.82* 1.18 — 2.76
NK3 −5.60 −3.43 1.20 −0.97 2.18

Cyclic voltammograms measured in degassed ACN with 0.1 M [n-Bu4N]PF6 as the supporting electrolyte with the scan rate = 150 mV s−1.

*Values were determined from the optical band gap.

2.4 Aggregation induced enhanced emission characteristics

To evaluate the AIEE characteristics, the emission characteristics of NK series molecules were examined in the mixture of acetone/water with a rising water volume ratio (ƒ w). With an increasing water ratio, a decrease in emission intensities was recorded due to the alteration in solvent polarity affecting the ICT mechanism in the excited state for all molecules. However, a significant increase in fluorescence emission intensities for NK2 and NK3 was observed at the critical point of the water content at which the aggregation occurred, supporting the AIEE mechanism. In Figure 7, steady-state fluorescence spectra of NK1, NK2, and NK3 and the relationship between the acetone/water mixture emission and only acetone emission (I/I 0) are presented.

Figure 7 Steady-state fluorescence emission spectra of NK1 (a), NK2 (b), and NK3 (c) in the mixture of acetone/water with different ƒ w and the relation between acetone/water mixture emission and pure acetone emission (I/I 0) (d).
Figure 7

Steady-state fluorescence emission spectra of NK1 (a), NK2 (b), and NK3 (c) in the mixture of acetone/water with different ƒ w and the relation between acetone/water mixture emission and pure acetone emission (I/I 0) (d).

A redshift was observed in the NK1 compound with increasing water content, which contributes to the maintenance of the supramolecular structure’s rigidity and is attributed to the bulk packing effects also seen in the previously described AIE/AIEE molecules [25]. For NK1, emission intensity was not changed up to 40% water content. To understand the effect of fluorine atoms on AIEE properties, the emission profile of NK2 was investigated in water/acetone mixtures. For NK2, fluorescence enhancement was observed when the water content increased from 0 to 10%. For molecules that do not have AIEE properties, the fluorescence emission intensity decreases as the water content increases. In contrast, no significant change in emission intensity was observed in the NK2 molecule up to 60% water content.

For the NK3, the maximum emission intensity was observed at 20% water content. The intensity gradually decreased with the increasing water content. After 60% water content, no emission was observed.

2.5 Thermal properties

Thermal properties of the molecules thermogravimetric analysis were examined to understand their thermal stability. The TGA thermogram of the molecules is given in Figure 8(a). According to the TGA thermogram, molecules showed a single and clear degradation step and chemical degradation starts above 200°C for all molecules. NK2 degradation temperature (T d) was higher than NK1. This result could be explained by the higher internal and external interactions. This might be attributed to halogen atoms, which lead to an increase in the thermal stability, melting temperature (T m), and T d values of the molecule with external and internal molecular bonds, respectively [26,27]. NK3 had the highest thermal stability among the series with a 405°C of degradation temperature. Additional thiophene rings might lead to more stability for molecules and increased molecular weight. The weight losses of molecules were found as 95, 97, and 83% at 600°C, respectively.

Figure 8 % weight change thermogram (a) and temperature difference thermogram (b) of NK1, NK2, and NK3.
Figure 8

% weight change thermogram (a) and temperature difference thermogram (b) of NK1, NK2, and NK3.

The differential thermal analysis (DTA) gives more information on the compounds, shown in Figure 8(b). Two main peaks were observed in the DTA thermogram. According to Figure 8(b), the first peaks showed the melting temperature (T m) of the compounds. T m values of samples were found as 65, 238, and 226°C for NK1, NK2, and NK3, respectively. With the increased molecular weight, T m values increased. The existence of the fluorine atoms might increase the polarity of the molecule, and this increased the T m value, too. The second peak showed the degradation temperature (T d) of samples. T d values of samples were found as 293, 295, and 475°C, respectively. The presence of the thiophene rings increased the T d value.

2.6 Crystallographic properties

The single crystals of Br-TBT were chosen for an X-ray crystallographic investigation. The optimized structure of the Br-TBT molecule is seen in Figure 9 and crystallographic features are given in Table S1. A proper single crystal of the Br-TBT was obtained by slow diffusion of THF. It was understood that the single crystal had a monoclinic crystal structure with dimensions of a = 20.831(2) Å, b = 3.8875(3) Å, c = 20.1835(18) Å, and Z = 1.

Figure 9 OLEX2 view of the crystal structure and the crystal packing views of Br-TBT.
Figure 9

OLEX2 view of the crystal structure and the crystal packing views of Br-TBT.

The lengths of the S–N bonds within the benzothiadiazole group have been found as 1.606(6) and 1.618(6) Å which is between the S–N single bond length (1.73 Å) and S═N double bond length (1.53 Å). The C–N bond lengths are 1.337(7) and 1.343(8) which is like the value for the N-heterocyclic molecules [28]. Some important bond angles and lengths of the molecule have been selected and presented in Table 3.

Table 3

Some important bond lengths and angles

Bond angles
S5 C20 Br1 120.4(4) S3 C9 Br2 120.4(4)
C17 C20 Br1 127.6(6) C19 C9 Br2 126.4(6)
C17 C20 S5 112.0(6) C19 C9 S3 113.1(6)
Bond lengths
S4 N6 1.606(6) S4 N7 1.618(6)
S5 C16 1.736(6) S5 C20 1.719(7)
S3 C9 1.712(7) S3 C12 1.725(7)
N6 C15 1.337(7) N7 C11 1.343(8)

In the crystal structure of the Br-TBT molecule, two thiophene rings are syn to each other. It can be attributed to strong S···N intramolecular interaction. In the thiophene groups, carbon atoms (C20 and C9) that are linked to the bromine atom have slightly distorted tetrahedral geometry because of the steric hindrance of sulfur atoms. The molecule is almost planar and rigid molecular conformation which results in high interchain charge transport. The mode of the 3D supramolecular packing framework of Br-TBT is known J-aggregation mode which can enhance the charge transfer throughout the molecules. J-aggregates generally produce a red shift in the absorption spectrum compared to solution [29]. The packing arrangement of the compound did have any π–π interactions owing to being nearly planar with torsional angles between C12–C8–C11–N7 = −2.2(10)ᵒ and C16 C10 C15 N6 = 1.5(10)ᵒ.

3 Conclusion

In this study, three small organic molecules with a benzothiadiazole core have been designed and characterized. The photophysical characteristics of the molecules have been investigated in different solvents to understand their behaviors for solvachromism. AIEE properties have been also examined for possible imagining applications and it has been understood that they were AIEgenic molecules. The introduction of fluorine atoms instead of the methyl group caused the band gap of the molecule to decrease and the AIEE property to increase. They showed high PLQY in solution (between 66 and 96%) and moderate in film phase (between 68 and 32%) which is needed for the high device performance in OLEDs. The decrease in PLQY can be explained by the aggregation in the film phase, resulting in quenching luminescence. The molecular structure of the Br-TBT has also been illuminated with a single-crystal X-ray study in this work first time. The crystal structure of the Br-TBT molecule showed an almost planar and rigid structure. The 3D packing of the structure showed a J-aggregation mode that increase the charge transfer between molecules. The study is quite comprehensive in terms of providing ideas for those working on molecule design not just for organic photovoltaic applications but also for cell imagining thanks to their AIEE properties and high PLQY values.

SI: CCDC 2260798 contains the supplementary crystallographic data for this article. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: + 44 1223 336033).

Acknowledgments

The author wants to thank Hakan Bilgili who passed away because of COVID-19. The author also wants to thank İzmir Katip Çelebi University Central Research Laboratory for the measurements of CV, TGA analysis, Raman analysis, and photophysical investigations.

  1. Funding information: There is no funding for this article.

  2. Author contributions: N.K. – conceptualization, data curation, formal analysis, investigation, methodology, visualization, writing – original draft and writing – review & editing.

  3. Conflict of interest: The author states no conflict of interest.

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

  5. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Received: 2023-09-28
Revised: 2023-10-17
Accepted: 2023-10-18
Published Online: 2023-11-03

© 2023 the author(s), published by De Gruyter

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

Articles in the same Issue

  1. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  2. Regular Articles
  3. A network-based correlation research between element electronegativity and node importance
  4. Pomegranate attenuates kidney injury in cyclosporine-induced nephrotoxicity in rats by suppressing oxidative stress
  5. Ab initio study of fundamental properties of XInO3 (X = K, Rb, Cs) perovskites
  6. Responses of feldspathic sandstone and sand-reconstituted soil C and N to freeze–thaw cycles
  7. Robust fractional control based on high gain observers design (RNFC) for a Spirulina maxima culture interfaced with an advanced oxidation process
  8. Study on arsenic speciation and redistribution mechanism in Lonicera japonica plants via synchrotron techniques
  9. Optimization of machining Nilo 36 superalloy parameters in turning operation
  10. Vacuum impregnation pre-treatment: A novel method for incorporating mono- and divalent cations into potato strips to reduce the acrylamide formation in French fries
  11. Characterization of effective constituents in Acanthopanax senticosus fruit for blood deficiency syndrome based on the chinmedomics strategy
  12. Comparative analysis of the metabolites in Pinellia ternata from two producing regions using ultra-high-performance liquid chromatography–electrospray ionization–tandem mass spectrometry
  13. The assessment of environmental parameter along the desalination plants in the Kingdom of Saudi Arabia
  14. Effects of harpin and carbendazim on antioxidant accumulation in young jujube leaves
  15. The effects of in ovo injected with sodium borate on hatching performance and small intestine morphology in broiler chicks
  16. Optimization of cutting forces and surface roughness via ANOVA and grey relational analysis in machining of In718
  17. Essential oils of Origanum compactum Benth: Chemical characterization, in vitro, in silico, antioxidant, and antibacterial activities
  18. Translocation of tungsten(vi) oxide/gadolinium(iii) fluoride in tellurite glasses towards improvement of gamma-ray attenuation features in high-density glass shields
  19. Mechanical properties, elastic moduli, and gamma ray attenuation competencies of some TeO2–WO3–GdF3 glasses: Tailoring WO3–GdF3 substitution toward optimum behavioral state range
  20. Comparison between the CIDR or sponge with hormone injection to induce estrus synchronization for twining and sex preselection in Naimi sheep
  21. Exergetic performance analyses of three different cogeneration plants
  22. Psoralea corylifolia (babchi) seeds enhance proliferation of normal human cultured melanocytes: GC–MS profiling and biological investigation
  23. A novel electrochemical micro-titration method for quantitative evaluation of the DPPH free radical scavenging capacity of caffeic acid
  24. Comparative study between supported bimetallic catalysts for nitrate remediation in water
  25. Persicaline, an alkaloid from Salvadora persica, inhibits proliferation and induces apoptosis and cell-cycle arrest in MCF-7 cells
  26. Determination of nicotine content in locally produced smokeless tobacco (Shammah) samples from Jazan region of Saudi Arabia using a convenient HPLC-MS/MS method
  27. Changes in oxidative stress markers in pediatric burn injury over a 1-week period
  28. Integrated geophysical techniques applied for petroleum basins structural characterization in the central part of the Western Desert, Egypt
  29. The impact of chemical modifications on gamma-ray attenuation properties of some WO3-reinforced tellurite glasses
  30. Microwave and Cs+-assisted chemo selective reaction protocol for synthesizing 2-styryl quinoline biorelevant molecules
  31. Structural, physical, and radiation absorption properties of a significant nuclear power plant component: A comparison between REX-734 and 316L SS austenitic stainless steels
  32. Effect of Moringa oleifera on serum YKL-40 level: In vivo rat periodontitis model
  33. Investigating the impact of CO2 emissions on the COVID-19 pandemic by generalized linear mixed model approach with inverse Gaussian and gamma distributions
  34. Influence of WO3 content on gamma rays attenuation characteristics of phosphate glasses at low energy range
  35. Study on CO2 absorption performance of ternary DES formed based on DEA as promoting factor
  36. Performance analyses of detonation engine cogeneration cycles
  37. Sterols from Centaurea pumilio L. with cell proliferative activity: In vitro and in silico studies
  38. Untargeted metabolomics revealing changes in aroma substances in flue-cured tobacco
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  40. Energy consumption, mechanical and metallographic properties of cryogenically treated tool steels
  41. Optimization of ultra-high pressure-assisted extraction of total phenols from Eucommia ulmoides leaves by response surface methodology
  42. Harpin enhances antioxidant nutrient accumulation and decreases enzymatic browning in stored soybean sprouts
  43. Physicochemical and biological properties of carvacrol
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  46. Experimental study on photocatalytic CO2 reduction performance of ZnS/CdS-TiO2 nanotube array thin films
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https://doi.org/10.1515/chem-2023-0150
Keywords for this article
benzothiadiazole; small organic molecule; molecular characterization; single crystal
Creative Commons
BY 4.0

Articles in the same Issue

  1. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  2. Regular Articles
  3. A network-based correlation research between element electronegativity and node importance
  4. Pomegranate attenuates kidney injury in cyclosporine-induced nephrotoxicity in rats by suppressing oxidative stress
  5. Ab initio study of fundamental properties of XInO3 (X = K, Rb, Cs) perovskites
  6. Responses of feldspathic sandstone and sand-reconstituted soil C and N to freeze–thaw cycles
  7. Robust fractional control based on high gain observers design (RNFC) for a Spirulina maxima culture interfaced with an advanced oxidation process
  8. Study on arsenic speciation and redistribution mechanism in Lonicera japonica plants via synchrotron techniques
  9. Optimization of machining Nilo 36 superalloy parameters in turning operation
  10. Vacuum impregnation pre-treatment: A novel method for incorporating mono- and divalent cations into potato strips to reduce the acrylamide formation in French fries
  11. Characterization of effective constituents in Acanthopanax senticosus fruit for blood deficiency syndrome based on the chinmedomics strategy
  12. Comparative analysis of the metabolites in Pinellia ternata from two producing regions using ultra-high-performance liquid chromatography–electrospray ionization–tandem mass spectrometry
  13. The assessment of environmental parameter along the desalination plants in the Kingdom of Saudi Arabia
  14. Effects of harpin and carbendazim on antioxidant accumulation in young jujube leaves
  15. The effects of in ovo injected with sodium borate on hatching performance and small intestine morphology in broiler chicks
  16. Optimization of cutting forces and surface roughness via ANOVA and grey relational analysis in machining of In718
  17. Essential oils of Origanum compactum Benth: Chemical characterization, in vitro, in silico, antioxidant, and antibacterial activities
  18. Translocation of tungsten(vi) oxide/gadolinium(iii) fluoride in tellurite glasses towards improvement of gamma-ray attenuation features in high-density glass shields
  19. Mechanical properties, elastic moduli, and gamma ray attenuation competencies of some TeO2–WO3–GdF3 glasses: Tailoring WO3–GdF3 substitution toward optimum behavioral state range
  20. Comparison between the CIDR or sponge with hormone injection to induce estrus synchronization for twining and sex preselection in Naimi sheep
  21. Exergetic performance analyses of three different cogeneration plants
  22. Psoralea corylifolia (babchi) seeds enhance proliferation of normal human cultured melanocytes: GC–MS profiling and biological investigation
  23. A novel electrochemical micro-titration method for quantitative evaluation of the DPPH free radical scavenging capacity of caffeic acid
  24. Comparative study between supported bimetallic catalysts for nitrate remediation in water
  25. Persicaline, an alkaloid from Salvadora persica, inhibits proliferation and induces apoptosis and cell-cycle arrest in MCF-7 cells
  26. Determination of nicotine content in locally produced smokeless tobacco (Shammah) samples from Jazan region of Saudi Arabia using a convenient HPLC-MS/MS method
  27. Changes in oxidative stress markers in pediatric burn injury over a 1-week period
  28. Integrated geophysical techniques applied for petroleum basins structural characterization in the central part of the Western Desert, Egypt
  29. The impact of chemical modifications on gamma-ray attenuation properties of some WO3-reinforced tellurite glasses
  30. Microwave and Cs+-assisted chemo selective reaction protocol for synthesizing 2-styryl quinoline biorelevant molecules
  31. Structural, physical, and radiation absorption properties of a significant nuclear power plant component: A comparison between REX-734 and 316L SS austenitic stainless steels
  32. Effect of Moringa oleifera on serum YKL-40 level: In vivo rat periodontitis model
  33. Investigating the impact of CO2 emissions on the COVID-19 pandemic by generalized linear mixed model approach with inverse Gaussian and gamma distributions
  34. Influence of WO3 content on gamma rays attenuation characteristics of phosphate glasses at low energy range
  35. Study on CO2 absorption performance of ternary DES formed based on DEA as promoting factor
  36. Performance analyses of detonation engine cogeneration cycles
  37. Sterols from Centaurea pumilio L. with cell proliferative activity: In vitro and in silico studies
  38. Untargeted metabolomics revealing changes in aroma substances in flue-cured tobacco
  39. Effect of pumpkin enriched with calcium lactate on iron status in an animal model of postmenopausal osteoporosis
  40. Energy consumption, mechanical and metallographic properties of cryogenically treated tool steels
  41. Optimization of ultra-high pressure-assisted extraction of total phenols from Eucommia ulmoides leaves by response surface methodology
  42. Harpin enhances antioxidant nutrient accumulation and decreases enzymatic browning in stored soybean sprouts
  43. Physicochemical and biological properties of carvacrol
  44. Radix puerariae in the treatment of diabetic nephropathy: A network pharmacology analysis and experimental validation
  45. Anti-Alzheimer, antioxidants, glucose-6-phosphate dehydrogenase effects of Taverniera glabra mediated ZnO and Fe2O3 nanoparticles in alloxan-induced diabetic rats
  46. Experimental study on photocatalytic CO2 reduction performance of ZnS/CdS-TiO2 nanotube array thin films
  47. Epoxy-reinforced heavy metal oxides for gamma ray shielding purposes
  48. Black mulberry (Morus nigra L.) fruits: As a medicinal plant rich in human health-promoting compounds
  49. Promising antioxidant and antimicrobial effects of essential oils extracted from fruits of Juniperus thurifera: In vitro and in silico investigations
  50. Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics
  51. Study on antioxidant and antimicrobial potential of chemically profiled essential oils extracted from Juniperus phoenicea (L.) by use of in vitro and in silico approaches
  52. Screening and characterization of fungal taxol-producing endophytic fungi for evaluation of antimicrobial and anticancer activities
  53. Mineral composition, principal polyphenolic components, and evaluation of the anti-inflammatory, analgesic, and antioxidant properties of Cytisus villosus Pourr leaf extracts
  54. In vitro antiproliferative efficacy of Annona muricata seed and fruit extracts on several cancer cell lines
  55. An experimental study for chemical characterization of artificial anterior cruciate ligament with coated chitosan as biomaterial
  56. Prevalence of residual risks of the transfusion-transmitted infections in Riyadh hospitals: A two-year retrospective study
  57. Computational and experimental investigation of antibacterial and antifungal properties of Nicotiana tabacum extracts
  58. Reinforcement of cementitious mortars with hemp fibers and shives
  59. X-ray shielding properties of bismuth-borate glass doped with rare earth ions
  60. Green supported silver nanoparticles over modified reduced graphene oxide: Investigation of its antioxidant and anti-ovarian cancer effects
  61. Orthogonal synthesis of a versatile building block for dual functionalization of targeting vectors
  62. Thymbra spicata leaf extract driven biogenic synthesis of Au/Fe3O4 nanocomposite and its bio-application in the treatment of different types of leukemia
  63. The role of Ag2O incorporation in nuclear radiation shielding behaviors of the Li2O–Pb3O4–SiO2 glass system: A multi-step characterization study
  64. A stimuli-responsive in situ spray hydrogel co-loaded with naringenin and gentamicin for chronic wounds
  65. Assessment of the impact of γ-irradiation on the piperine content and microbial quality of black pepper
  66. Antioxidant, sensory, and functional properties of low-alcoholic IPA beer with Pinus sylvestris L. shoots addition fermented using unconventional yeast
  67. Screening and optimization of extracellular pectinase produced by Bacillus thuringiensis SH7
  68. Determination of polyphenols in Chinese jujube using ultra-performance liquid chromatography–mass spectrometry
  69. Synergistic effects of harpin and NaCl in determining soybean sprout quality under non-sterile conditions
  70. Field evaluation of different eco-friendly alternative control methods against Panonychus citri [Acari: Tetranychidae] spider mite and its predators in citrus orchards
  71. Exploring the antimicrobial potential of biologically synthesized zero valent iron nanoparticles
  72. NaCl regulates goldfish growth and survival at three food supply levels under hypoxia
  73. An exploration of the physical, optical, mechanical, and radiation shielding properties of PbO–MgO–ZnO–B2O3 glasses
  74. A novel statistical modeling of air pollution and the COVID-19 pandemic mortality data by Poisson, geometric, and negative binomial regression models with fixed and random effects
  75. Treatment activity of the injectable hydrogels loaded with dexamethasone In(iii) complex on glioma by inhibiting the VEGF signaling pathway
  76. An alternative approach for the excess lifetime cancer risk and prediction of radiological parameters
  77. Panax ginseng leaf aqueous extract mediated green synthesis of AgNPs under ultrasound condition and investigation of its anti-lung adenocarcinoma effects
  78. Study of hydrolysis and production of instant ginger (Zingiber officinale) tea
  79. Novel green synthesis of zinc oxide nanoparticles using Salvia rosmarinus extract for treatment of human lung cancer
  80. Evaluation of second trimester plasma lipoxin A4, VEGFR-1, IL-6, and TNF-α levels in pregnant women with gestational diabetes mellitus
  81. Antidiabetic, antioxidant and cytotoxicity activities of ortho- and para-substituted Schiff bases derived from metformin hydrochloride: Validation by molecular docking and in silico ADME studies
  82. Antioxidant, antidiabetic, antiglaucoma, and anticholinergic effects of Tayfi grape (Vitis vinifera): A phytochemical screening by LC-MS/MS analysis
  83. Identification of genetic polymorphisms in the stearoyl CoA desaturase gene and its association with milk quality traits in Najdi sheep
  84. Cold-acclimation effect on cadmium absorption and biosynthesis of polyphenolics, and free proline and photosynthetic pigments in Spirogyra aequinoctialis
  85. Analysis of secondary metabolites in Xinjiang Morus nigra leaves using different extraction methods with UPLC-Q/TOF-MS/MS technology
  86. Nanoarchitectonics and performance evaluation of a Fe3O4-stabilized Pickering emulsion-type differential pressure plugging agent
  87. Investigating pyrolysis characteristics of Shengdong coal through Py-GC/MS
  88. Extraction, phytochemical characterization, and antifungal activity of Salvia rosmarinus extract
  89. Introducing a novel and natural antibiotic for the treatment of oral pathogens: Abelmoschus esculentus green-formulated silver nanoparticles
  90. Optimization of gallic acid-enriched ultrasonic-assisted extraction from mango peels
  91. Effect of gamma rays irradiation in the structure, optical, and electrical properties of samarium doped bismuth titanate ceramics
  92. Combinatory in silico investigation for potential inhibitors from Curcuma sahuynhensis Škorničk. & N.S. Lý volatile phytoconstituents against influenza A hemagglutinin, SARS-CoV-2 main protease, and Omicron-variant spike protein
  93. Physical, mechanical, and gamma ray shielding properties of the Bi2O3–BaO–B2O3–ZnO–As2O3–MgO–Na2O glass system
  94. Twofold interpenetrated 3D Cd(ii) complex: Crystal structure and luminescent property
  95. Study on the microstructure and soil quality variation of composite soil with soft rock and sand
  96. Ancient spring waters still emerging and accessible in the Roman Forum area: Chemical–physical and microbiological characterization
  97. Extraction and characterization of type I collagen from scales of Mexican Biajaiba fish
  98. Finding small molecular compounds to decrease trimethylamine oxide levels in atherosclerosis by virtual screening
  99. Prefatory in silico studies and in vitro insecticidal effect of Nigella sativa (L.) essential oil and its active compound (carvacrol) against the Callosobruchus maculatus adults (Fab), a major pest of chickpea
  100. Polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6: Synthesis, crystal structures, and catalytic activity
  101. Using calcined waste fish bones as a green solid catalyst for biodiesel production from date seed oil
  102. Influence of the addition of WO3 on TeO2–Na2O glass systems in view of the feature of mechanical, optical, and photon attenuation
  103. Naringin ameliorates 5-fluorouracil elicited neurotoxicity by curtailing oxidative stress and iNOS/NF-ĸB/caspase-3 pathway
  104. GC-MS profile of extracts of an endophytic fungus Alternaria and evaluation of its anticancer and antibacterial potentialities
  105. Green synthesis, chemical characterization, and antioxidant and anti-colorectal cancer effects of vanadium nanoparticles
  106. Determination of caffeine content in coffee drinks prepared in some coffee shops in the local market in Jeddah City, Saudi Arabia
  107. A new 3D supramolecular Cu(ii) framework: Crystal structure and photocatalytic characteristics
  108. Bordeaux mixture accelerates ripening, delays senescence, and promotes metabolite accumulation in jujube fruit
  109. Important application value of injectable hydrogels loaded with omeprazole Schiff base complex in the treatment of pancreatitis
  110. Color tunable benzothiadiazole-based small molecules for lightening applications
  111. Investigation of structural, dielectric, impedance, and mechanical properties of hydroxyapatite-modified barium titanate composites for biomedical applications
  112. Metal gel particles loaded with epidermal cell growth factor promote skin wound repair mechanism by regulating miRNA
  113. In vitro exploration of Hypsizygus ulmarius (Bull.) mushroom fruiting bodies: Potential antidiabetic and anti-inflammatory agent
  114. Alteration in the molecular structure of the adenine base exposed to gamma irradiation: An ESR study
  115. Comprehensive study of optical, thermal, and gamma-ray shielding properties of Bi2O3–ZnO–PbO–B2O3 glasses
  116. Lewis acids as co-catalysts in Pd-based catalyzed systems of the octene-1 hydroethoxycarbonylation reaction
  117. Synthesis, Hirshfeld surface analysis, thermal, and selective α-glucosidase inhibitory studies of Schiff base transition metal complexes
  118. Protective properties of AgNPs green-synthesized by Abelmoschus esculentus on retinal damage on the virtue of its anti-inflammatory and antioxidant effects in diabetic rat
  119. Effects of green decorated AgNPs on lignin-modified magnetic nanoparticles mediated by Cydonia on cecal ligation and puncture-induced sepsis
  120. Treatment of gastric cancer by green mediated silver nanoparticles using Pistacia atlantica bark aqueous extract
  121. Preparation of newly developed porcelain ceramics containing WO3 nanoparticles for radiation shielding applications
  122. Utilization of computational methods for the identification of new natural inhibitors of human neutrophil elastase in inflammation therapy
  123. Some anticancer agents as effective glutathione S-transferase (GST) inhibitors
  124. Clay-based bricks’ rich illite mineral for gamma-ray shielding applications: An experimental evaluation of the effect of pressure rates on gamma-ray attenuation parameters
  125. Stability kinetics of orevactaene pigments produced by Epicoccum nigrum in solid-state fermentation
  126. Treatment of denture stomatitis using iron nanoparticles green-synthesized by Silybum marianum extract
  127. Characterization and antioxidant potential of white mustard (Brassica hirta) leaf extract and stabilization of sunflower oil
  128. Characteristics of Langmuir monomolecular monolayers formed by the novel oil blends
  129. Strategies for optimizing the single GdSrFeO4 phase synthesis
  130. Oleic acid and linoleic acid nanosomes boost immunity and provoke cell death via the upregulation of beta-defensin-4 at genetic and epigenetic levels
  131. Unraveling the therapeutic potential of Bombax ceiba roots: A comprehensive study of chemical composition, heavy metal content, antibacterial activity, and in silico analysis
  132. Green synthesis of AgNPs using plant extract and investigation of its anti-human colorectal cancer application
  133. The adsorption of naproxen on adsorbents obtained from pepper stalk extract by green synthesis
  134. Treatment of gastric cancer by silver nanoparticles encapsulated by chitosan polymers mediated by Pistacia atlantica extract under ultrasound condition
  135. In vitro protective and anti-inflammatory effects of Capparis spinosa and its flavonoids profile
  136. Wear and corrosion behavior of TiC and WC coatings deposited on high-speed steels by electro-spark deposition
  137. Therapeutic effects of green-formulated gold nanoparticles by Origanum majorana on spinal cord injury in rats
  138. Melanin antibacterial activity of two new strains, SN1 and SN2, of Exophiala phaeomuriformis against five human pathogens
  139. Evaluation of the analgesic and anesthetic properties of silver nanoparticles supported over biodegradable acacia gum-modified magnetic nanoparticles
  140. Review Articles
  141. Role and mechanism of fruit waste polyphenols in diabetes management
  142. A comprehensive review of non-alkaloidal metabolites from the subfamily Amaryllidoideae (Amaryllidaceae)
  143. Discovery of the chemical constituents, structural characteristics, and pharmacological functions of Chinese caterpillar fungus
  144. Eco-friendly green approach of nickel oxide nanoparticles for biomedical applications
  145. Advances in the pharmaceutical research of curcumin for oral administration
  146. Rapid Communication
  147. Determination of the contents of bioactive compounds in St. John’s wort (Hypericum perforatum): Comparison of commercial and wild samples
  148. Retraction
  149. Retraction of “Two mixed-ligand coordination polymers based on 2,5-thiophenedicarboxylic acid and flexible N-donor ligands: The protective effect on periodontitis via reducing the release of IL-1β and TNF-α”
  150. Topical Issue on Phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  151. Anti-plasmodial potential of selected medicinal plants and a compound Atropine isolated from Eucalyptus obliqua
  152. Anthocyanin extract from black rice attenuates chronic inflammation in DSS-induced colitis mouse model by modulating the gut microbiota
  153. Evaluation of antibiofilm and cytotoxicity effect of Rumex vesicarius methanol extract
  154. Chemical compositions of Litsea umbellata and inhibition activities
  155. Green synthesis, characterization of silver nanoparticles using Rhynchosia capitata leaf extract and their biological activities
  156. GC-MS analysis and antibacterial activities of some plants belonging to the genus Euphorbia on selected bacterial isolates
  157. The abrogative effect of propolis on acrylamide-induced toxicity in male albino rats: Histological study
  158. A phytoconstituent 6-aminoflavone ameliorates lipopolysaccharide-induced oxidative stress mediated synapse and memory dysfunction via p-Akt/NF-kB pathway in albino mice
  159. Anti-diabetic potentials of Sorbaria tomentosa Lindl. Rehder: Phytochemistry (GC-MS analysis), α-amylase, α-glucosidase inhibitory, in vivo hypoglycemic, and biochemical analysis
  160. Assessment of cytotoxic and apoptotic activities of the Cassia angustifolia aqueous extract against SW480 colon cancer
  161. Biochemical analysis, antioxidant, and antibacterial efficacy of the bee propolis extract (Hymenoptera: Apis mellifera) against Staphylococcus aureus-induced infection in BALB/c mice: In vitro and in vivo study
  162. Assessment of essential elements and heavy metals in Saudi Arabian rice samples underwent various processing methods
  163. Two new compounds from leaves of Capparis dongvanensis (Sy, B. H. Quang & D. V. Hai) and inhibition activities
  164. Hydroxyquinoline sulfanilamide ameliorates STZ-induced hyperglycemia-mediated amyleoid beta burden and memory impairment in adult mice
  165. An automated reading of semi-quantitative hemagglutination results in microplates: Micro-assay for plant lectins
  166. Inductively coupled plasma mass spectrometry assessment of essential and toxic trace elements in traditional spices consumed by the population of the Middle Eastern region in their recipes
  167. Phytochemical analysis and anticancer activity of the Pithecellobium dulce seed extract in colorectal cancer cells
  168. Impact of climatic disturbances on the chemical compositions and metabolites of Salvia officinalis
  169. Physicochemical characterization, antioxidant and antifungal activities of essential oils of Urginea maritima and Allium sativum
  170. Phytochemical analysis and antifungal efficiency of Origanum majorana extracts against some phytopathogenic fungi causing tomato damping-off diseases
  171. Special Issue on 4th IC3PE
  172. Graphene quantum dots: A comprehensive overview
  173. Studies on the intercalation of calcium–aluminium layered double hydroxide-MCPA and its controlled release mechanism as a potential green herbicide
  174. Synergetic effect of adsorption and photocatalysis by zinc ferrite-anchored graphitic carbon nitride nanosheet for the removal of ciprofloxacin under visible light irradiation
  175. Exploring anticancer activity of the Indonesian guava leaf (Psidium guajava L.) fraction on various human cancer cell lines in an in vitro cell-based approach
  176. The comparison of gold extraction methods from the rock using thiourea and thiosulfate
  177. Special Issue on Marine environmental sciences and significance of the multidisciplinary approaches
  178. Sorption of alkylphenols and estrogens on microplastics in marine conditions
  179. Cytotoxic ketosteroids from the Red Sea soft coral Dendronephthya sp.
  180. Antibacterial and biofilm prevention metabolites from Acanthophora spicifera
  181. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  182. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part II
  183. Green synthesis, characterization, and evaluation of antibacterial activities of cobalt nanoparticles produced by marine fungal species Periconia prolifica
  184. Combustion-mediated sol–gel preparation of cobalt-doped ZnO nanohybrids for the degradation of acid red and antibacterial performance
  185. Perinatal supplementation with selenium nanoparticles modified with ascorbic acid improves hepatotoxicity in rat gestational diabetes
  186. Evaluation and chemical characterization of bioactive secondary metabolites from endophytic fungi associated with the ethnomedicinal plant Bergenia ciliata
  187. Enhancing photovoltaic efficiency with SQI-Br and SQI-I sensitizers: A comparative analysis
  188. Nanostructured p-PbS/p-CuO sulfide/oxide bilayer heterojunction as a promising photoelectrode for hydrogen gas generation
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