Effects of peripheral and nonperipheral substitution to the spectroscopic, electrochemical and spectroelectrochemical properties of metallophthalocyanines

Electrochimica Acta

Volumn 106, Issue , 2013, Pages 541-555

  Arican, Duygu ^a   Arici, Mürsel ^b   Ugur, Ahmet Lütfi ^c   Erdoǧmuş, Ali ^d   Koca, Atif ^a  

^a MARMARA UNIVERSITY   (Turkey)

^b ESKISEHIR OSMANGAZI UNIVERSITY   (Turkey)

^c ÇANAKKALE ONSEKIZ MART UNIVERSITY   (Turkey)

^d YILDIZ TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Chronocolorimetry; Oxygen reduction reaction; Spectroelectrochemistry; Thiol substituted metallophthalocyanines. Electrochemistry

Indexed keywords

ABSORPTION SPECTROSCOPY; CHEMICAL ANALYSIS; COBALT COMPOUNDS; DYES; ELECTROCHEMISTRY; ELECTROLYTIC REDUCTION; MANGANESE; MASS SPECTROMETRY; METALS; MOLECULAR OXYGEN; NITROGEN COMPOUNDS; REDOX REACTIONS; REDUCTION; SPECTROELECTROCHEMISTRY;

CHRONOCOLORIMETRY; ELECTRONIC ABSORPTION SPECTROSCOPY; METALLOPHTHALOCYANINES; NONPOLAR ORGANIC SOLVENTS; OXYGEN REDUCTION REACTION; REDOX ACTIVE METAL CENTERS; SPECTROELECTROCHEMICAL ANALYSIS; SPECTROELECTROCHEMICAL PROPERTIES;

SYNTHESIS (CHEMICAL);

EID: 84879817825     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2013.04.166     Document Type: Article

References (50)

1. C. C. Leznoff, A. B. P. Lever, Phthalocyanines: properties and applications, VCH, New York, 1989.
2. G. Guillaud, J. Simon, J. Germain, Metallophthalocyanines: Gas sensors, resistors and field effect transistors, Coordination Chemistry Reviews 178 (1998) 1433-1484. (Pubitemid 128452088)
3. T. Komatsu, K. Ohta, T. Fujimoto, I. Yamamoto, Chromic materials. Part 1.-Liquid-crystalline behaviour and electrochromism in bis (octakis- nalkylphthalocyaninato) lutetium (III) complexes, Journal of Materials Chemistry 4 (1994) 533-536.
4. C. G. Claessens, W. J. Blau, M. Cook, M. Hanack, R. J. M. Nolte, T. Torres, D. Wo Èhrle, Phthalocyanines and phthalocyanine analogues: The quest for applicable optical properties, Monatshefte für Chemie/Chemical Monthly 132 (2001) 3-11.
5. A. Erdoǧmuş, T. Nyokong, Novel, soluble, FluXoro functional substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties, Dyes and Pigments 86 (2010) 174-181.
6. R. Bonnett, Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy, Chemical Society Reviews 24 (1995) 19-33.
7. J. Obirai, N. P. Rodrigues, F. Bedioui, T. Nyokong, Synthesis, spectral and electrochemical properties of a new family of pyrrole substituted cobalt, iron, manganese, nickel and zinc phthalocyanine complexes, Journal of Porphyrins and Phthalocyanines 7 (2003) 508-520.
8. G. A. Meerovich, N. L. Torshina, V. B. Loschenov, A. A. Stratonnikov, A. I. Volkova, G. N. Vorozhtsov, O. L. Kaliya, E. A. Lukyanets, B. Y. Kogan, A. V. Butenin, E. A. Kogan, O. P. Gladskikh, L. N. Polyakova, The experimental study of PDT with aluminum sulphophthalocyanine using sodium ascorbate and hyperbaric oxygenation, in: P Soc Photo-Opt Ins, 1999, pp. 68-76.
9. K. Ishii, N. Kobayashi, K. Kadish, K. Smith, R. Guilard, The Porphyrin Handbook, Elsevier Science, New York, 2003.
10. H. Pekbelgin Karaoglu, A. Gül, M. B. Kocak, Synthesis and characterization of a new tetracationic phthalocyanine, Dyes and Pigments 76 (2008) 231-235. (Pubitemid 47034795)
11. G. Lu, M. Bai, R. Li, X. Zhang, C. Ma, P. C. Lo, D. K. P. Ng, J. Jiang, Lanthanide (iii) double-decker complexes with octaphenoxy-or octathiophenoxyphthalocyaninato ligands - revealing the electron-withdrawing nature of the phenoxy and thiophenoxy groups in the double-decker complexes, European Journal of Inorganic Chemistry 2006 (2006) 3703-3709.
12. A. Erdogmuş, A. Koca, A. L. Ugur, I. Erden, Synthesis, electrochemical and spectroelectrochemical properties of highly soluble tetra substituted phthalocyanines with [4-(thiophen-3-yl)-phenoxy], Synthetic Metals 161 (2011) 1319-1329.
13. N. Nombona, T. Nyokong, The synthesis, cyclic voltammetry and spectroelectrochemical studies of Co (II) phthalocyanines tetra-substituted at the α and β positions with phenylthio groups, Dyes and Pigments 80 (2009) 130-135.
14. M. Kandaz, M. N. Yaraşir, T. Güney, A. Koca, Both alcohol and halogenated solvents soluble soft-metal sensor functional phthalocyanines: synthesis, electrochemistry, spectroelectrochemistry, Journal of Porphyrins and Phthalocyanines 13 (2009) 712-721.
15. A. E. G. Gürek, Ö. Bekarolu, Octakis (alkylthio)-substituted phthalocyanines and their interactions with silver (I) and palladium (II) ions, Journal of the Chemical Society, Dalton Transactions (1994) 1419-1423.
16. K. Takahashi, M. Kawashima, Y. Tomita, M. Itoh, Synthesis and spectral and electrochemical properties of 2, 3, 9, 10, 16, 17, 23, 24- octabutylthiophthalocyaninatozinc (II), Inorganica Chimica Acta 232 (1995) 69-73.
17. K. Ozoemena, P. Westbroek, T. Nyokong, Long-term stability of a gold electrode modified with a self-assembled monolayer of octabutylthiophthalocyaninatocobalt (II) towards l-cysteine detection, Electrochemistry Communications 3 (2001) 529-534.
18. K. I. Ozoemena, T. Nyokong, Electrochemical behaviour of thiol-derivatised zinc (II) phthalocyanine complexes and their self-immobilised films at gold electrodes, Microchemical Journal 75 (2003) 241-247.
19. V. N. Nemykin, E. A. Lukyanets, Synthesis of substituted phthalocyanines, Arkivoc (2010) 136-208.
20. E. A. Lukyanets, V. N. Nemykin, The key role of peripheral substituents in the chemistry of phthalocyanines and their analogs, Journal of Porphyrins and Phthalocyanines 14 (2010) 1-40.
21. D. A. Makarov, N. A. Kuznetsova, O. A. Yuzhakova, L. P. Savvina, O. L. Kaliya, E. A. Lukyanets, V. M. Negrimovskii, M. G. Strakhovskaya, Effects of the degree of substitution on the physicochemical properties and photodynamic activity of zinc and aluminum phthalocyanine polycations, Russian Journal of Physical Chemistry A+ 83 (2009) 1044-1050.
22. D. Wohrle, M. Eskes, K. Shigehara, A. Yamada, A Simple Synthesis of 4, 5-Disubstituted 1, 2-Dicyanobenzenes and 2, 3, 9, 10, 16, 17, 23, 24-Octasubstituted Phthalocyanines, Synthesis-Stuttgart (1993) 194-196.
23. J. H. Zagal, F. Bedioui, J. P. Dodelet, N4-Macrocyclic Metal Complexes, Springer, New York, NY, 2006.
24. S. Griveau, F. Bedioui, Electrocatalytic oxidation of 2-mercaptoethanol by electropolymerized cobalt porphyrin film on vitreous carbon electrodes, Electroanalysis 13 (2001) 253-256. (Pubitemid 32244691)
25. C. A. Caro, F. Bedioui, J. H. Zagal, Electrocatalytic oxidation of nitrite on a vitreous carbon electrode modified with cobalt phthalocyanine, Electrochimica Acta 47 (2002) 1489-1494. (Pubitemid 34181933)
26. M. Arici, D. Arican, A. L. Ugur, A. Erdogmus, A. Koca, Synthesis, spectroscopic, electrochemical and spectroelectrochemical properties of metal free, manganese, and cobalt phthalocyanines bearing peripherally octakis-[4-(thiophen-3-yl)-phenoxy] substituents, Electrochimica Acta 87 (2013) 554-566.
27. H. T. Akcay, R. Bayrak, U. Demirbas, A. Koca, H. Kantekin, I. Degirmencioglu, Synthesis, electrochemical and spectroelectrochemical properties of peripherally tetra-imidazole substituted metal free and metallophthalocyanines, Dyes and Pigments 96 (2013) 483-494.
28. B. Ceken, M. Kandaz, A. Koca, Electrochemical hydrogen peroxide sensorbased on cobalt phthalocyanine captured in polyaniline film on a glassy carbon electrode, Journal of Porphyrins and Phthalocyanines 16 (2012) 380-389.
29. H. K. Yildiz, S. E. Korkut, A. Koca, M. K. Sener, 3, 4- Ethylenedioxythiophene substituted phthalocyanines, Synthetic Metals 161 (2011) 1946-1952.
30. A. Koca, A. Kalkan, Z. A. Bayir, Electrocatalytic oxygen reduction and hydrogen evolution reactions on phthalocyanine modified electrodes: Electrochemical, in situ spectroelectrochemical, and insituelectrocolorimetric monitoring, Electrochimica Acta 56 (2011) 5513-5525.
31. M. Arici, D. Arican, A. L. Ugur, A. Erdogmuş, A. Koca, Electrochemical and spectroelectrochemical characterization of newly synthesized manganese, cobalt, iron and copper phthalocyanines, Electrochimica Acta 78 (2012) 554-566.
32. J. Zhang, PEM Fuel Cell Electrocatalysts and Catalyst Layers: Fundamentals and Applications, Springer Verlag, London, 2008.
33. B. Winther-Jensen, O. Winther-Jensen, M. Forsyth, D. R. MacFarlane, High rates of oxygen reduction over a vapor phase-polymerized pedot electrode, Science 321 (2008) 671-674.
34. A. Koca, Electrochemical and in situ spectroelectrochemical monitoring of the interaction between cobaltphthalocyanines and molecular oxygen in aprotic media, Journal of Electroanalytical Chemistry 655 (2011) 128-139.
35. C. Öztürk, A. Erdogmuş, M. Durmuş, A. L. Ugur, F. Kiliçarslan, İ. Erden, Highly soluble 3, 4-(dimethoxyphenylthio) substituted phthalocyanines: Synthesis, photophysical and photochemical studies, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 86 (2011) 423-431.
36. M. J. Stillman, T. Nyokong, in: C. C. Leznoff, A. B. P. Lever (Eds.), Phthalocyanines: Properties and Applications, vol. 1, VCH, New York, 1989 (Chapter3).
37. A. Lever, P. Minor, J. Wilshire, Electrochemistry of manganese phthalocyanine in nonaqueous media, Inorganic Chemistry 20 (1981) 2550-2553.
38. M. N. Yaraşir, M. Kandaz, A. Koca, B. Salih, Polytopic cation receptor functional phthalocyanines: Synthesis, characterization, electrochemistry and metal ion binding, Polyhedron 26 (2007) 1139-1147.
39. A. Alemdar, A. R. Özkaya, M. Bulut, Preparation, characterization, electrochemistry and in situ spectroelectrochemistry of novel α-tetra[7-oxo-3-(2-chloro-4fluorophenyl) coumarin]-substituted metal-free, cobalt and zinc phthalocyanines, Synthetic Metals 160 (2010) 1556-1565.
40. I. A. Akinbulu, S. Khene, T. Nyokong, Surface properties of self-assembled monolayer films of tetra-substituted cobalt, iron and manganese alkylthio phthalocyanine complexes, Electrochimica Acta 55 (2010) 7085-7093.
41. F. Matemadombo, M. D. Maree, K. I. Ozoemena, P. Westbroek, T. Nyokong, Synthesis, electrochemical and spectroelectrochemical studies of octaphenylthiosubstituted phthalocyanines, Journal of Porphyrins and Phthalocyanines 9 (2005) 484-490.
42. P. Kissinger, W. R. Heineman, Laboratory Techniques in Electroanalytical Chemistry, Revised and Expanded, CRC, New York, 1996.
43. A. Lever, E. Milaeva, G. Speier, The redox chemistry of metallophthalocyanines in solutions, in: C. C. Leznoff, A. B. P. Lever (Eds.), Phthalocyanines: Properties and Applications, vol. 2, VCH, New York, 1989.
44. B. Akkurt, E. Hamuryudan, Enhancement of solubility via esterification: Synthesis and characterization of octakis (ester)-substituted phthalocyanines, Dyes and Pigments 79 (2008) 153-158.
45. C. C. Leznoff, L. S. Black, A. Hiebert, P. W. Causey, D. Christendat, A. Lever, Red manganese phthalocyanines from highly hindered hexadecaalkoxyphthalocyanines, Inorganica Chimica Acta 359 (2006) 2690-2699.
46. B. Simicglavaski, S. Zecevic, E. Yeager, Study of phthalocyanines in aqueous solutions and adsorbed on electrode surfaces, Journal of the Electrochemical Society 134 (1987) C130.
47. G. Mbambisa, P. Tau, E. Antunes, T. Nyokong, Synthesis and electrochemical properties of purple manganese (III) and redtitanium (IV) phthalocyanine complexes octa-substituted at non-peripheral positions with pentylthio groups, Polyhedron 26 (2007) 5355-5364.
48. B. Agboola, K. I. Ozoemena, T. Nyokong, Electrochemical properties of benzylmercapto and dodecylmercapto tetra substituted nickel phthalocyanine complexes: Electrocatalytic oxidation of nitrite, Electrochimica Acta 51 (2006) 4379-4387.
49. D. Kulac, M. Bulut, A. Altindal, A. R. Özkaya, B. Salih, Ö. Bekaroglu, Synthesis and characterization of novel 4-nitro-2-(octyloxy) phenoxy substituted symmetrical and unsymmetrical Zn (II), Co (II) and Lu (III) phthalocyanines, Polyhedron 26 (2007) 5432-5440.
50. Z. Jin, K. Nolan, C. McArthur, A. Lever, C. Leznoff, Synthesis, electrochemical and spectroelectrochemical studies of metal-free 2, 9, 16, 23-tetraferrocenylphthalocyanine, Journal of Organometallic Chemistry 468 (1994) 205-212.