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Synthesis of metallophthalocyanines with four oxy-2,2-diphenylacetic acid substituents and their structural and electronic properties

  • Sakar Mübarak Abdalrazaq , Beyza Cabir , Selçuk Gümüş and Mehmet Salih Ağırtaş EMAIL logo
Published/Copyright: October 4, 2016
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 22 Issue 5

Abstract

The synthesis and characterization of new copper-, magnesium- and cobalt- phthalocyanine complexes are reported. It appears that these complexes are not aggregated in THF in the concentration range of 1×10−5–1×10−6m. Additional structural and electronic data about the new complexes were obtained by calculations with the application of density functional theory at B3LYP/6-31G(d, p) level.

Keywords: aggregation; electronic structure; phthalocyanine; synthesis

Introduction

Phthalocyanines are planar aromatic macrocycles consisting of four isoindole units, which make an 18 π electron aromatic system delocalized over an arrangement of alternating carbon and nitrogen atoms. For many years, phthalocyanines have been important dyestuffs for textiles and inks, as a consequence of their dark green-blue color; their absorption spectra show an intense Q-band in the visible region, usually centered at 620–700 nm. Phthalocyanines are thermally and chemically stable compounds and can withstand intense electromagnetical radiation. Another remarkable feature is their structural versatility. The two hydrogen atoms of the central cavity can be replaced by more than 70 metals and a variety of substituents can be incorporated, both at the periphery of the macrocycle and/or at the axial positions, thus allowing fine tuning of the physical properties [1, 2]. Phthalocyanines and their metal complexes have attracted attention because of their applications in material science [1, 2] including liquid crystal [3, 4], organic solar cells [5], catalysis [6], semiconductors [7], dyes and pigments [8, 9], non-linear optical materials [10, 11] and organic light-emitting diodes [12]. They are also used in photodynamic therapy (PDT) of cancer [13, 14]. However, because of the hydrophobic nature of the phthalocyanine system, these compounds have a strong tendency to aggregate in solution, which limits their application [15]. The introduction of bulky groups to phthalocyanine can lower aggregation to some extent [16]. Physico-chemical properties of phthalocyanines can be modified by changing the type of metal ion in the central cavity or by incorporating substituents on the peripheral (β), non-peripheral (α), or axial positions [17], including long alkyl [18] or alkoxy chains [19] and heterocyclic groups [20]. Dyestuffs containing carboxylic group are advantageous because they can be anchored onto the hydroxyl-bearing oxide surface. Recent studies have indicated that carboxyl carrying phthalocyanines show interesting photophysical and photochemical properties [21].

In this paper we report the synthesis and characterization of phthalocyanines bearing oxy-2,2-diphenylacetic acid substituents on the peripheral positions and their metal complexes. It appears that the metal complexes show negligible aggregation in tetrahydrofuran.

Results and discussion

Synthesis and characterization

The synthetic route to metallophthalocyanines 4–6 is shown in Scheme 1. The starting material 2-(3,4-dicyanophenoxy)-2,2-diphenylacetic acid (3) was prepared by a reaction between 2-hydroxy-2,2-diphenylacetic acid (2) and 4-nitrophthalonitrile (1) in the presence of anhydrous K2CO3 in dry DMSO under a nitrogen atmosphere at room temperature for 2 days. The phthalocyanines 4–6 were synthesized by cyclization of substrate 3 in the presence of CoCl2, MgCl2 and CuCl2, respectively, under N2 atmosphere. Compounds 3–6 were characterized by elemental analysis and spectral methods.

Scheme 1 The route for the synthesis of compound 3–6.
Scheme 1

The route for the synthesis of compound 3–6.

1H NMR spectra of compound 4 and 6 could not be obtained due to their paramagnetic property.

Computational analysis

Figure 1 shows the geometry optimized structure of the selected cobalt(II) phthalocyanine complex 4 (top and side views). The charge distributions in the center of all complexes 4–6, obtained by natural bond order analysis, are shown in Figure 2 [22]. The computations reveal square-planar geometry. The charge distribution depends on the metal atom. As can be seen from Figure 2, the formal charge +2 of the metal atom at the center of the structure decreases to a net charge of +1.713 (5), 1.255 (4) and 1.210 (6), which is a consequence of charge donation from coordinating nitrogen atoms. All the donor nitrogens have been computed to possess negative charges. The coordinating nitrogen atoms are richer in electrons than the connecting nitrogen atoms, which might be a result of the absence of imino hydrogen atoms. The expected −1 formal charge on these atoms changes to −0.685 upon coordination to the metal atom. After geometry optimizations, the structures were subjected to TD-DFT calculations at the same basis set [B3LYP/6-31G(d, p)] to compute the electronic spectra of the phthalocyanine compounds. Transition energies and molecular orbital energies and schemes were predicted for singlet state excitations. The highest occupied molecular orbital (HOMO) implies the outermost filled orbital and behaves as an electron donor. On the other hand, the lowest unoccupied molecular orbital (LUMO) can be considered as the unfilled orbital with lowest energy and it behaves as an electron acceptor. HOMO and LUMO are also called the frontier molecule orbitals (FMOs). The energy gap between FMOs gives information about the chemical stability of a molecule and it is an important parameter in terms of electronic transport properties. In Figure 3, a part of the orbital energies (in Hartree) and three-dimensional HOMO and LUMO energy schemes for Mg complex 5 are given. Both HOMO and LUMO are spread throughout the molecule except for the metal at the center. The computed HOMO and LUMO energies for Mg complex 5 are −4.62 and −2.55 eV, respectively.

Figure 1 Top and side view of geometry optimized structure of Co complex (4).
Figure 1

Top and side view of geometry optimized structure of Co complex (4).

Figure 2 Charge distribution at the center of the phthalocyanine complexes.
Figure 2

Charge distribution at the center of the phthalocyanine complexes.

Figure 3 The frontier part of the molecular orbital energies and 3D HOMO and LUMO energy schemes for Mg complex 5.
Figure 3

The frontier part of the molecular orbital energies and 3D HOMO and LUMO energy schemes for Mg complex 5.

The excitation energies (eV), oscillator strengths (f) and absorption wavelengths (λmax, nm) of UV–vis electron absorption spectra of these compounds were calculated in gas phase by the application of TD-DFT/B3LYP method with 6-31G(d, p) basis set and are presented in Table 1. Molecular orbital energies indicate that transitions from HOMO to LUMO are responsible for the Q band of the experimental spectrum.

Table 1

Calculated absorption wavelength (λmax, nm), excitation energies (eV) and oscillator strengths (f) for Mg complex 5.

ComplexTransitionProbabilityλmaxExcitation energyOscillator strength
5H→L0.59597633.331.95760.5484
H→L+10.59608631.971.96190.5492
H-1→L+10.57715422.372.93540.0473

UV-vis measurements

The electronic absorption spectra of compounds 4–6 were recorded in THF over a concentration range of 10−6–10−5m (Figures 4–6). All spectra show a typical phthalocyanine Soret band around 336, 354 and 344 nm for compounds 4–6, respectively. An intense long wavelength π-π* transition, the Q-band, is characteristic of the UV-vis absorption spectra of phthalocyanines, with the respective peaks at 670, 696 and 696 nm. The lack of concentration dependence for absorption spectra recorded at the range of 10−6–10−5m suggests that complexes 4–6 do not undergo any appreciable aggregation in THF under these conditions.

Figure 4 Aggregation study of compound 4 in THF at 2.03×10−5, 1.52×10−5, 1.14×10−5, 8.58×10−6, 6.43×10−6, 4.82×10−6 and 3.62×10−6m concentrations.
Figure 4

Aggregation study of compound 4 in THF at 2.03×10−5, 1.52×10−5, 1.14×10−5, 8.58×10−6, 6.43×10−6, 4.82×10−6 and 3.62×10−6m concentrations.

Figure 5 Aggregation study of compound 5 in THF at 2.08×10−5, 1.56×10−5, 1.56×10−5, 8.78×10−6, 6.59×10−6, 4.94×10−6, 3.70×10−6m concentrations.
Figure 5

Aggregation study of compound 5 in THF at 2.08×10−5, 1.56×10−5, 1.56×10−5, 8.78×10−6, 6.59×10−6, 4.94×10−6, 3.70×10−6m concentrations.

Figure 6 Aggregation study of compound 6 in THF at 2.02×10−5, 1.52×10−5, 1.14×10−5, 8.55×10−6, 6.41×10−6, 4.81×10−6, 3.60×10−6m concentrations.
Figure 6

Aggregation study of compound 6 in THF at 2.02×10−5, 1.52×10−5, 1.14×10−5, 8.55×10−6, 6.41×10−6, 4.81×10−6, 3.60×10−6m concentrations.

Conclusions

Metal phthalocyanines bearing [carboxy(diphenyl)methyl]oxy groups on the peripheral positions were synthesized. These compounds are soluble in organic solvents and, apparently, do not undergo aggregation in tertrahydrofuran. Computational results provide additional structural and electronic information about the complexes.

Experimental

The solvents were purified according to standard procedures [23] and stored over molecular sieves 4 Å. All reactions were carried out under a dry nitrogen atmosphere. Melting points were measured on an electrothermal apparatus. Electronic spectra were recorded on a Hitachi U-2900 spectrophotometer. FT-IR spectra were recorded on a Thermo Scientific FT-IR spectrophotometer. 1H NMR spectra were recorded on an Agilent 400 MHz spectrometer with tetramethylsilane as internal standard.

2-(3,4-Dicyanophenoxy)-2,2-diphenylacetic acid (3)

A mixture of 2-hydroxy-2,2-diphenylacetic acid (2, 0.80 g, 3.5 mmol) and 4-nitrophthalonitrile (1, 0.50 g, 2.89 mmol) in dimethyl sulfoxide (15 mL) was stirred at room temperature for 15 min, then treated with K2CO3 (5 g, 36 mmol) and stirred for an additional 48 h. The mixture was poured into ice-cold water and acidified to pH 1 with hydrochloride acid. The resultant precipitate of 3 was washed with petroleum ether and dried: Yield 0.52 g (51%); mp 125°C; 1H NMR (DMSO-d6): δ 13.15(exchangeable with D2O), 9.03, 8.67, 8.66, 8.43, 8.41, 6.33; IR: 3398, 3109, 3051, 3032, 2924, 2881, 2854, 2630, 2480, 2241, 1720, 1654, 1608, 1585, 1539, 1492, 1446, 1411, 1354, 1300, 1246, 1176, 1053, 1033, 979, 929, 902, 856, 802 cm−1. Anal. Calcd for C22H14N2O3 (354.36 g/mol): C, 74.57; H, 3.98; N, 7.91. Found: C, 74.69; H, 4.43; N, 7.56.

Synthesis of metal complexes 4–6

A mixture of 2-(3,4-dicyanophenoxy)-2,2-diphenylacetic acid (3, 0.10 g, 0.28 mmol) and CoCl2, MgCl2 or CuCl2 (0.02 g) was grounded in a quartz crucible and heated in a sealed glass tube for 5 min at 230°C. After cooling to room temperature, the reaction was terminated by pouring the solution into an aqueous solution of 2 m HCl. After standing overnight, the resultant precipitate of 4–6 was filtered, washed with water to a neutral pH and dried. Silica gel chromatography eluting with tetrahydrofuran gave a green solid.

Cobalt(II) 2,10,16,24–tetrakis{[carboxy(diphenyl)methyl]oxy}phthalocyanine (4)

Yield 0.05 g (49%); UV-vis (THF): λmax (log ε) 670 (5.26), 336 nm (5.18); IR:3734, 3618, 3433, 3089, 3066, 2988, 2873, 1732, 1608, 1531, 1488, 1388, 1338, 1253, 1145, 1091, 933, 906, 852, 810 cm−1. Anal. Calcd for C88H56 Co N8O12 (1476.37 g/mol): C, 71.59; H, 3.82; N, 7.59. Found: C, 71.75; H, 4.22; N, 7.24. This compound is soluble in acetone, acetonitrile, dichloromethane, THF, DMF and DMSO.

Magnesium(II) 2,10,16,24–tetrakis{[carboxy(diphenyl)methyl]oxy}phthalocyanine (5)

Yield 0.032 g (32%); UV-Vis (THF): λmax (log ε) 696 (5.08), 624(4.59), 354 nm (4.83); 1H NMR (DMSO-d6): δ 6.85, 6.84, 6.71, 6.68, 6.62, 6.60, 6.56; IR: 3637, 3441, 3089, 2954, 2920, 2866, 1728, 1608, 1527, 1481, 1435, 1396, 1338, 1230, 1141, 1087, 1041, 972, 925, 852, 810 cm−1. Anal. Calcd for C88H56 N8O12Mg (1441.74 g/mol): C, 73.31; H, 3.92; N, 7.77. Found: C, 72.07; H, 4.19; N, 7.35. This compound is soluble in acetone, dichloromethane, THF, DMF and DMSO.

Copper(II) 2,10,16,24–tetrakis{[carboxy(diphenyl)methyl]oxy} phthalocyanine (6)

Yield 0.03 g (29%); UV-Vis (THF): λmax (log ε): 696 (5.09), 624(4.66), 342 nm (4.90); IR: 3626, 3429, 3089, 3066, 2958, 2912, 2870, 1728, 1608, 1531, 1485, 1338, 1333, 1257, 1145, 1091, 933, 906, 852, 810 cm−1. Anal. Calcd for C88H56 Cu N8O12 (1480.98 g/mol): C, 71.37; H, 3.81; N, 7.57. Found: C, 71.81; H, 4.23; N, 7.21. This compound is soluble in acetone, dichloromethane, THF, DMF and DMSO.

Computations

3-Dimensional structures of the compounds were obtained by geometry optimization using density functional theory at B3LYP/6-31G(d, p) level with no symmetry restrictions. All computational calculations were performed using Gaussian 09 package program [24]. The vibrational analysis for each metal phthalocyanine complex did not yield any imaginary frequencies, which indicates that the structure of each molecule has at least a local minimum on the potential energy surface. The normal mode analysis was performed for 3N-6 vibrational degrees of freedom, N being the number of atoms in the structure of the phthalocyanine compounds.

The time-dependent density functional theory (TD-DFT) calculations were done to obtain the vertical excitation energies, oscillator strengths (f) and excited state compositions in terms of excitations between the occupied and virtual orbitals for metal complexes [25, 26]. The TD-DFT method with the same basis set was used to obtain absorption wavelengths and the oscillation strength (f) within the UV-vis region.

Acknowledgments

This study was supported by the Research Fund of Yüzüncü Yıl University (2015-FBE-D041).

References

[1] Ma, D.; Pan, S.; Zhang, T.; Huang, B.; Xie, S.; Yang, H. Y. P. Comparation of multiple terminal functional groups dendrimer silicon(IV) phthalocyanines:photoinduced electron/energy transfer and electrochemical properties. Dyes Pigm.2016, 127, 78–86.10.1016/j.dyepig.2015.12.019Search in Google Scholar

[2] Jiang, J. FunctionalPhthalocyanine Molecular Materials; Springer-Verlag: Berlin, 2010.10.1007/978-3-642-04752-7Search in Google Scholar

[3] Garland, A. D.; Chambrier, I.; Cammidge, A. N.; Cook, M. J. Design and synthesis of liquid crystalline phthalocyanines: combinations of substituents that promote the discotic nematic mesophase. Tetrahedron2015, 71, 7310–7314.10.1016/j.tet.2015.04.006Search in Google Scholar

[4] Staden, J. F. Application of phthalocyanines in flow- and sequential-injection analysis and microfluidics systems: a review. Talanta2015, 139, 75–88.10.1016/j.talanta.2015.02.026Search in Google Scholar PubMed

[5] Bilgiçli, A. T.; Yaraşır, M. N.; Kandaz, M.; İlik, C.; Demir, A.; Bağcı, S. Nonperipheral tetraphthalocyanines bearing alkyl chain moiety: Synthesis, characterization and fabrication of the OFET based on phthalocyanine. Synth. Met.2015, 206, 33–41.10.1016/j.synthmet.2015.05.002Search in Google Scholar

[6] Dinçer, H.; Mert, H.; Çalışkan, E.; Atmaca, G. Y.; Erdoğmuş, A. Synthesis and photophysicochemical studies of poly(ethylene glycol) conjugated symmetrical and asymmetrical zinc phthalocyanines. J. Mol. Struct.2015, 1102, 190–196.10.1016/j.molstruc.2015.08.067Search in Google Scholar

[7] Çakır, V.; Çakır, D.; Pişkin, M.; Durmuş, M.; Bıyıklıoğlu, Z. New peripherally and non-peripherally tetra-substituted water soluble zinc phthalocyanines: synthesis, photophysics and photochemistry. J. Organomet. Chem.2015, 783, 120–129.10.1016/j.jorganchem.2015.02.021Search in Google Scholar

[8] Ağırtaş, M. S.; Karatas, C.; Gümüş, S.; Okumuş, V. Synthesis of some novel phthalocyanines with methyl 2-(oxy)-2,2-diphenylacetate substituents, evaluation of their antioxidant-antibacterial activities and electronic properties. Z. Anorg. Allg. Chem.2015, 641, 442–447.10.1002/zaac.201400445Search in Google Scholar

[9] Ağırtaş, M. S. Synthesis and characterization of novel symmetrical phthalocyanines substituted with four benzo[d][1,3]dioxol-5-ylmethoxy groups. Inorg. Chim. Acta2007, 360, 2499–2502.10.1016/j.ica.2006.12.029Search in Google Scholar

[10] Yao, C.-B.; Yan, X.-Y.; Sun, D.-W.; Sui, Y.-L.; Li, J.; Sun, W.-J.; Li, Q.-H.; Yang, S.-B. Ultrafast dynamics of excited state of phenoxy-phthalocyanines in solution. Opt. Laser Tech.2016, 76, 53–57.10.1016/j.optlastec.2015.07.019Search in Google Scholar

[11] Duruk, E. G.; Yenilmez, H. Y.; Koca, A.; Bayır, Z. A. Electrochemical, spectroelectrochemical and catalytical properties of new Cu(II) and Co(II) phthalocyanines. Synth. Met.2016, 214, 82–91.10.1016/j.synthmet.2016.01.012Search in Google Scholar

[12] Kahouech, M. S.; Hriz, K.; Touaiti, S.; Bassem, J. New anthracene-based-phtalocyanine semi-conducting materials: synthesis and optoelectronic properties. Mater. Res. Bull. 2016, 75, 144–154.10.1016/j.materresbull.2015.11.010Search in Google Scholar

[13] Tshangana, C.; Nyokong, T. Photophysical properties of gallium octacarboxy phthalocyanines conjugated to CdSe@ZnS quantum dots. Spectrochim. Acta Part A.2015, 151, 397–404.10.1016/j.saa.2015.06.086Search in Google Scholar PubMed

[14] Ogbodu, R. O.; Ndhundhuma, I. K.; Nyokong, A. T. Photodynamic therapy effect of zinc monoamino phthalocyanine-folic acid conjugate adsorbed on single walled carbon nanotubes on melanoma cells. Spectrochim. Acta Part A 2015, 137, 1120–1125.10.1016/j.saa.2014.09.033Search in Google Scholar PubMed

[15] Ağırtaş, M. S. Non-aggregating phthalocyanines with bulky 2,4-di-tert-butylphenoxy-substituents. Dyes Pigments2007, 74, 490–493.10.1016/j.dyepig.2006.03.009Search in Google Scholar

[16] Ağırtaş, M. S.; Güven, M. E.; Gümüş, S.; Özdemir, S.; Dündar, A. Metallo and metal free phthalocyanines bearing (4-(1(4-phenoxyphenyl)-1-phenylethyl)phenol substituents: synthesis, characterization, aggregation behavior, electronic, antioxidant and antibacterial properties. Synth. Met.2014, 195, 177–184.10.1016/j.synthmet.2014.06.004Search in Google Scholar

[17] Tillo, A.; Stolarska, M.; Kryjewski, M.; Popenda, L.; Sobotta, L.; Jurga, S.; Mielcarek, J.; Goslinski, T. Phthalocyanines with bulky substituents at non-peripheral positions – synthesis and physico-chemical properties. Dyes Pigments2016, 127, 110–115.10.1016/j.dyepig.2015.12.017Search in Google Scholar

[18] Cammidge, A. N.; Tseng, C.-H.; Chambrier, I.; Hughes, D. L.; Cook, M. J. Phthalocyanines bearing bulky cycloalkylmethyl substituents on non-peripheral sites. Tetrahedron Lett.2009, 50, 5254–5256.10.1016/j.tetlet.2009.07.016Search in Google Scholar

[19] Leznoff, C. C.; Black, L. S.; Hiebert, A.; Causey, P. W.; Christendat, D.; Lever, A. B. P. Red manganese phthalocyanines from highly hindered hexadecaalkoxyphthalocyanines. Inorg. Chim. Acta2006, 359, 2690–2699.10.1016/j.ica.2005.10.046Search in Google Scholar

[20] Kucinska, M.; Skupin-Mrugalska, P.; Szczolko, W.; Sobotta, L.; Sciepura, M.; Tykarska, E. Phthalocyanine derivatives possessing 2-(morpholin-4-yl)ethoxy groups as potential agents for photodynamic therapy. J. Med. Chem.2015, 58, 2240–2255.10.1021/acs.jmedchem.5b00052Search in Google Scholar PubMed

[21] Mahmiani, Y.; Sevim, A. M.; Gül, A. Photocatalytic degradation of 4-chlorophenol under visible light by using TiO2 catalysts impregnated with Co(II) and Zn(II) phthalocyanine derivatives. J. Photochem. Photobiol. A. 2016, 321, 24–32.10.1016/j.jphotochem.2015.12.015Search in Google Scholar

[22] Weinhold, F.; Landis, C. R. Natural bond orbıtals and extensions of localized bonding concepts. Chem. Educ. Res. Pract. Eur.2001, 2, 91–104.10.1039/B1RP90011KSearch in Google Scholar

[23] Armarego, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals; 7th ed. Butterwordh-Heinemann: Oxford, 2013.10.1016/B978-0-12-382161-4.00004-2Search in Google Scholar

[24] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 09; Wallingford, CT, Gaussian Inc., 2009.Search in Google Scholar

[25] Casida, M. Time Dependent Density Functional Response Theory for Molecules. In Recent Advances in Density Functional Methods. D. P. Chong, Ed., vol. 1. World Scientific: Singapore, 1995, p. 155.10.1142/9789812830586_0005Search in Google Scholar

[26] Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: characterization and correction of the time-dependent local density approximation ionization threshold. J. Chem. Phys.1998, 108, 4439–4449.10.1063/1.475855Search in Google Scholar

Received: 2016-8-1
Accepted: 2016-8-22
Published Online: 2016-10-4
Published in Print: 2016-10-1

©2016 Walter de Gruyter GmbH, Berlin/Boston

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https://doi.org/10.1515/hc-2016-0120
Keywords for this article
aggregation; electronic structure; phthalocyanine; synthesis
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Articles in the same Issue

  1. Frontmatter
  2. Preliminary Communications
  3. Efficient synthesis of 4-amino-2,6-dichloropyridine and its derivatives
  4. Reactions of 3-arylmethylene-3H-furan(pyrrol)-2-ones with azomethine ylide: synthesis of substituted azaspirononenes
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  7. Structural characterization of copper complexes with chiral 1,2,4-triazine-oxazoline ligands
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