1,2,4-triazole-5(4H)-one based novel peripherally tetrasubstituted metal-free and metallophthalocyanines: Synthesis, characterization, and electrochemical and spectroelectrochemical properties

References

• Tan, C. X.; Shi, Y. X.; Weng, J. Q.; Liu, X. H.; Li, B. J.; Zhao, W. G. Synthesis and antifungal activity of 1, 2,4-triazole derivatives containing cyclopropane moiety. Lett. Drug Des. Discov. 2012, 9, 431.
   Web of Science ®Google Scholar
• Liu, X. H.; Pan, L.; Weng, J. Q.; Tan, C. X.; Li, Y. H.; Wang, B. L.; Li, Z. M. Synthesis, structure, and biological activity of novel (oxdi/tri)azoles derivatives containing 1,2,3-thiadiazole or methyl moiety. Mol. Divers. 2012, 16, 251.
   PubMed Web of Science ®Google Scholar
• Liu, X. H.; Tan, C. X.; Weng, J. Q. Phase transfer-catalyzed, one-pot synthesis of some novel N-pyrimidinyl-N'-nicotinyl thiourea derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 558.
   Web of Science ®Google Scholar
• Su, N. N.; Li, Y.; Yu, S. J.; Zhang, X.; Liu, X. H.; Zhao, W. G. Microwave-assisted synthesis of some novel 1,2,3-triazoles by click chemistry, and their biological activity. Res. Chem. Intermed. 2013, 39, 759.
   Web of Science ®Google Scholar
• Griffin, D. A.; Mannion, S. K. Preparation of substituted triazolyl butanoates as plant growth regulators. Eur. Pat. Appl. EP. 1986, 199.
   Google Scholar
• Holla, B. S.; Poojary, K. A.; Kalluraya, B.; Gowda, P. V. Synthesis, characterisation and antifungal activity of some N-bridged heterocycles derived from 3-(3-bromo-4-methoxyphenyl)-4-amino-5-mercapto-1,2,4-triazole. Farmaco 1996, 51, 793.
   PubMedGoogle Scholar
• Asthalatha, B. V.; Narayana, B.; Vijaya Raj, K. K.; Suchetha Kumari, N. Synthesis of some new bioactive 3-amino-2-mercapto-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one derivatives. Eur. J. Med. Chem. 2007, 42, 1049.
   PubMed Web of Science ®Google Scholar
• Bhat, A. R.; Bhat, G. V.; Shenoy, G. G. Synthesis and in-vitro antimicrobial activity of new 1,2,4-triazoles. J. Pharm. Pharmacol. 2001, 53, 267.
   PubMed Web of Science ®Google Scholar
• Turan-Zitoui, G.; Kaplancikli, Z. A.; Erol, K.; Kilic, F. S. Synthesis and analgesic activity of some triazoles and triazolothiadiazines. Il Farmaco. 1999, 54, 218.
   PubMedGoogle Scholar
• Invidiata, F. P.; Simoni, D.; Scintu, F.; Pinna. N. 3,6-Disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles: Synthesis, antimicrobial and antiviral activity. II. Farmaco. 1996, 51, 659.
   PubMedGoogle Scholar
• Broto, P.; Moreau, G.; Vandycke, C. Molecular structures: Perception, autocorrelation descriptor and SAR studies. Use of the autocorrelation descriptors in the QSAR study of two non-narcotic analgesic series. Eur. J. Med. Chem. 1984, 9, 79.
   Google Scholar
• Molvi, K. I.; Vasu, K. K.; Yerande, S. G.; Sudarsanam, V.; Haque, N. Syntheses of new tetrasubstituted thiophenes as novel anti-inflammatory agents. Eur. J. Med. Chem. 2007, 42, 1049.
   PubMed Web of Science ®Google Scholar
• Shishoo, C. J.; Devani, M. B.; Jain, K. S.; Bhadti, V. S.; Shishoo, S. M.; Pathak, U. S.; Ananthan, S.; Rathod, I. S. Synthesis of some 2,4 ‐ diamino ‐6 ‐substituted ‐amino‐ 5‐ aryl‐ pyrimidines. Indian J. Chem. 1989, 28B, 83.
   Google Scholar
• Drabent, K.; Ciunik, Z.; Ozarowski, A. X-ray crystal structures, electron paramagnetic resonance, and magnetic studies on strongly antiferromagnetically coupled mixed mu-hydroxide-mu-N(1),N(2)-triazole-bridged one dimensional linear chain copper(II) complexes. Inorg. Chem. Commun. 2008, 8, 3358.
   Web of Science ®Google Scholar
• Diaz Garcia, M. A.; Ledoux, I.; Duro, J. A.; Torres, T.; Agullo-Lopez, F.; Zyss, J. Third-order nonlinear optical properties of soluble octasubstituted metallophthalocyanines. J. Phys. Chem. 1994, 98, 8761.
   Web of Science ®Google Scholar
• Simon, J.; Bassoul, P. (Eds.). Design of Molecular Materials. Supramolecular Engineering, Wiley: Chishester, 2000, p. 197.
   Google Scholar
• Eichlorn, H.; Wöhrle, D.; Pressner, D. Glasses of new 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines forming thermotropic and lyotropic discotic mesophases. Lig. Cryst. 1997, 22, 643.
   Web of Science ®Google Scholar
• Nyokong, T. In: N4-macrocyclic Metal Complexes, vol. 18. Zagal, J.; Bedioui, F.; Dodelet, J. P. (Eds.); Springer: NewYork, 2006, p. 63.
   Google Scholar
• Wöhrle, D.; Kreienhoop, L.; Schlettwein, D. Phthalocyanines and related macrocycles in organic photovoltaic junctions. In: Phthalocyanine—Properties and Applications, Leznoff, L. (Ed.); VCH-Publishers: New York, 1996, pp. 219–284.
   Google Scholar
• Okura, I. Kodansha Ltd. and Gordon and Breach Science Publishers: Tokyo, 2000, p. 45.
   Google Scholar
• Mukherjee, B.; Mukherjee, M. Programmable memory in organic field-effect transistor based on lead phthalocyanine. Org. Electron. 2009, 10, 1282.
   Web of Science ®Google Scholar
• Zhang, Y. J.; Hu, W. P. Field-effect transistor chemical sensors of single nanoribbon of copper phthalocyanine. China Ser. B. Chem. 2009, 52, 751.
   Web of Science ®Google Scholar
• Ben-Hur, E. In Henderson, B. W.; Dougherty, T. J. (Eds.); Proceedings of Laser Surgery. Marcel Dekker: New York, 1992, p. 63.
   Google Scholar
• Koksal, Y.; Tanak, H.; Unluer, D.; Isık, S. 4-(4-Methoxyphenethyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one. Acta Cryst. 2010, 66, 2158.
   Google Scholar
• Achar, B. N.; Fohlen, G. M.; Parker, J.; Keshavayya, A. J. Synthesis and structural studies of metal(II)4,9,16,23-phthalocyanine tetraamines. Polyhedron 1987, 6, 1463.
   Web of Science ®Google Scholar
• Agboola, B.; Ozoemena, K. I.; Nyokong, T. Synthesis and electrochemical characterisation of benzylmercapto and dodecylmercapto tetra substituted cobalt, iron, and zinc phthalocyanines complexes. Electrochim. Acta. 2006, 51, 4379.
   Google Scholar
• Arslanoglu, Y.; Hamuryudan, E. Synthesis and derivatization of near-IR absorbing titanylphthalocyanines with dimethylaminoethylsulfanyl substituents. Dyes Pigments. 2007, 75, 150.
   Web of Science ®Google Scholar
• Nalwa, H.; Shirk, J.; Leznoff, C.; Lever, A.; Leznoff, C. C. (Eds.). Phthalocyanines, Properties and Applications, vol. 4; VCH Publishers, Inc.: New York, 1996, pp. 79–181.
   Google Scholar
• Milaeva, E. R.; Speier, G.; Lever, A. B. P. In: Leznoff, C. C.; Lever, A. B. P. (Eds.); The Phthalocyanines, Properties and Applications. Wiley; 1992, pp. 162–227.
   Google Scholar
• Chauke, V. P.; Arslanoglu, Y.; Nyokong, T. Synthesis and photophysical behaviour of tantalum and titanium phthalocyanines in the presence of gold nanoparticles: Photocatalysis towards the oxidation of cyclohexene. Polyhedron 2011, 30, 2132.
   Web of Science ®Google Scholar
• Koca, A.; Dincer, H.; Kocak, M.; Gul, A. Electrochemical characterization of Co(II) and Pd(II) phthalocyanines carrying diethoxymalonyl and carboxymethyl substituents. Russian J. Electrochem. 2006, 42, 31.
   Web of Science ®Google Scholar
• Kobayashi, N.; Lam, H.; Nevin, W. A.; Janda, P.; Leznoff, C. C.; Lever, A. B. P. Electrochemistry and spectroelectrochemistry of 1,8-naphthalene-linked and 1,8-anthracene-linked cofacial binuclear metallophthalocyanines—new mixed-valence metalophthalocyanines. Inorg. Chem. 1990, 29, 3415.
   Web of Science ®Google Scholar
• Koca, A. Electrochemical and in situ spectroelectrochemical monitoring of the interaction between cobaltphthalocyanines and molecular oxygen in aprotic media. J. Electroanal. Chem. 2011, 655, 128.
   Web of Science ®Google Scholar
• Aktas, A.; Acar, I.; Koca, A.; Bıyıklıoglu, Z.; Kantekin, H. Synthesis, characterization, electrochemical and spectroelectrochemical properties of peripherally tetra-substituted metal-free and metallophthalocyanines. Dyes Pigment 2013, 99, 613.
   Web of Science ®Google Scholar
• Ozkaya, A. R.; Alemdar, A.; Bulut, M. Preparation, characterization, electrochemistry and in situ spectroelectrochemistry of novel α-tetra[7-oxo-3-(2-chloro-fluorophenyl)coumarin]-substituted metal-free, cobalt and zinc phthalocyanines. Synth. Met. 2010, 160, 1556.
   Web of Science ®Google Scholar
• Arican, D.; Aktas, A.; Kantekin, H.; Koca, A. Electrochromism of electropolymerized phthalocyanine-tetrahydroquinoline dyads. J. Electrochem. Soc. 2014, 161, 670.
   Web of Science ®Google Scholar
• Aktas, A.; Acar, I.; Bıyıklıoglu, Z.; Saka, E. T.; Kantekin, H. Synthesis, electrochemistry of metal-free, copper, titanium phthalocyanines and investigation of catalytic activity of cobalt, iron phthalocyanines on benzyl alcohol oxidation bearing 4-{2-[3-trifluoromethyl)phenoxy]ethoxy} groups. Synth. Metals 2014, 198, 212.
   Web of Science ®Google Scholar
• Koca, A.; Kalkan, A.; Bayir, Z. A. Electrochemical, in situ spectroelectrochemical, in situ electrocolorimetric and electrocatalytic characterization ofmetallophthalocyanines bearing four dioctylaminocarbonyl biphenyloxy substituents. Electroanalysis 2010, 22, 310.
   Web of Science ®Google Scholar
• Nevin, W. A.; Liu, W.; Melnik, M.; Lever, A. B. P. Spectroelectrochemistry of cobalt and iron tetrasulfonated phthalocyanines. J. Electroanal. Chem. 1986, 213, 217.
   Web of Science ®Google Scholar
• Erdogmus, A.; Koca, A.; Ugur, A. L.; Erden, I. Synthesis, electrochemical and spectroelectrochemical properties of highly soluble tetra substituted phthalocyanines with [4-(thiophen-3-yl)-phenoxy]. Synth. Metals. 2011, 161, 1319.
   Web of Science ®Google Scholar
• Koca, A.; Arslanoglu, Y.; Hamuryudan, E. Voltammetric and spectroelectrochemical properties of titanylphthalocyanines bearing catecholato and naphthalenediolato moieties. J. Electroanal. Chem. 2008, 616, 107.
   Web of Science ®Google Scholar
• Canlica, M.; Nyokong, T. Synthesis and photophysical properties of metal free, titanium, magnesium and zinc phthalocyanines substituted with a single carboxyl and hexylthio groups. Polyhedron 2011, 30, 1975.
   Web of Science ®Google Scholar
• Demir, F.; Erdogmus, A.; Koca, A. Titanyl phthalocyanines: Electrochemical and spectroelectrochemical characterizations and electrochemical metal ion sensor applications of Langmuir films. J. Electroanal. Chem. 2013, 703, 117.
   Web of Science ®Google Scholar