Deniz Kutlu TARAKCI, İlke GÜROL

Synthesis and characterization of tetra-substituted titanium(IV) phthalocyanines with axial ligand

In this paper, the synthesis and characterization of peripheral tetra-2-(2-ethyloxyethyloxy)ethyloxy substituted oxo-titanium phthalocyanines (TiOPcs) are reported. The reaction of 2,2,3,3-tetrafluoropropoxy substituted and [2-(2-ethoxyethoxy)ethoxy] substituted TiOPcs (1 and 3) with 4-[(6-hydroxyhexyl)oxy]benzene-1,2-diol as a strongly chelating oxygen donor ligand is described. Compounds 1a and 3a bearing the hydroxyl group as an axial ligand of the bulky group are converted into a thiol group (1c and 3c). The new compounds are characterized by elemental analysis, FT-IR, 1H NMR, and mass spectrometry. While the fluoropropoxy substituted TiOPc has good solubility in polar solvents such as acetone and THF, the other TiOPc is soluble in chloroform.

Anahtar Kelimeler:

TiOPc, titanium phthalocyanines, axial substitution

Synthesis and characterization of tetra-substituted titanium(IV) phthalocyanines with axial ligand

Keywords:

TiOPc, titanium phthalocyanines, axial substitution,

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Santiago, J.; Sugino, T.; Shimizu , Y. Mol. Cryst. Liq. Cryst. A 1999, 332, 3007–3014.
Yu, T. M.; Yang, S. M. ; Fu, C. Y.; Liu, M. H.; Hsu, L.; Chang, H. Y.; Liu, C. H. Sens. Actuators, B 2013, 180, 35–
Verma, R. S.; Dasgupta, R.; Kumar, N.; Ahlawat, S.; Uppal, A.; Gupta, P. K. Pramana 2014, 82, 433–437.
Vasseur, K.; Rand, B. P.; Cheyns, D.; Temst, K.; Froyen, L.; Heremans, P. J. Phys.Chem. Lett. 2012, 3, 2395–2400.
Yu, L.; Shi, W.; Lin, L.; Liu, Y.; Li, R.; Peng, T.; Li, X. Dalton Trans. 2014, 43, 8421–8430.
Faassen, E. V.; Kerp, H. Sens. Actuators, B 2003, 88, 329–333.
Simmendinger, W.; Oprea, A.; Barsan, N.; Weimar, U. Sens. Actuators, B 2013, 179, 54–60.
Generosi, A.; Paci, B.; Albertini, V. R.; Perfetti, P.; Paoletti, A. M.; Pennesi, G.; Rossi, G.; Caminiti, R. App. Phys. Lett. 2005, 87, 181904/1–181904/3.
Paoletti, A. M.; Pennesi, G.; Rossi, G.; Generosi, A.; Paci, B.; Albertini, V. R. Sensors 2009, 9, 5277–5297.
Burat, A. K.; Bayir, Z. A.; Koca, A. Electroanalysis 2012, 24, 338–348.
Esenpinar, A. A.; Ozkaya, A. R.; Bulut, M. J. Organomet. Chem. 2011, 696, 3873–3881.
Biyiklioglu, Z. Dyes Pigments 2013, 99, 727–732.
Arslanoglu, Y.; Hayran, E.; Hamuryudan, E. Dyes Pigments 2013, 97, 340–346.
Akcay, H. T.; Bayrak, R.; Demirbas, U.; Koca, A.; Kantekin, H.; Degirmencioglu, I. Dyes Pigments 2013, 96, 483– 4
Erdogmus, A.; Koca, A.; Ugur, A. L.; Erden, I. Synth. Met. 2011, 161, 1319–1329.
Tau, P.; Nyokong, T. Electrochim. Acta 2007, 52, 4547–4553.
Osmanbas, O. A.; Koca, A.; Ozcesmeci, I.; Okur, A. I.; Gul, A. Electrochim. Acta 2008, 53, 4969–4980.
Ceken, B.; Kandaz, M.; Koca, A. Synth. Met. 2012, 162, 1524–1530.
Liu, L.; Guo, L. P.; Bo, X. J.; Bai, J.; Cui, X. J. Anal. Chim. Acta 2010, 673, 88–94.
Atilla, D.; Durmus, M.; Yilmaz, O.; Gurek, A. G.; Ahsen, V.; Nyokong, T. Eur. J. Inorg. Chem. 2007, 22, 3573– 35
Ali, H.; Van Lier, J. E. Chem. Rev. 1999, 99, 2379–2450.
Canlica, M.; Nyokong, T. Polyhedron 2011, 30, 1975–1981.
Un, I.; Zorlu, Y.; Ibısoglu, H.; Dumoulin, F.; Ahsen V. Turk. J. Chem. 2013, 37, 394–404.
Somani, P. R.; Radhakrishnan, S. Mater. Chem. Phys. 2003, 77, 117–133.
Ozcelik, S.; Karaoglan, G. K.; Gumrukcu, G.; Gul, A. Turk. J. Chem. 2012, 36, 899–906.
Garcia, J.; Gonzalez, A.; Gouloumis, A.; Maya, E. M.; Perez, M. D.; Rey, B. D.; Vazquez, P.; Torres, T. Turk. J. Chem. 1998, 22, 23–31.
Hanack, M. Turk. J. Chem. 1998, 22, 13–22.
Rahimi, R.; Tadjarodi, A.; Imani, M.; Rabbani, M.; Safalou Moghaddam, S.; Kerdari, H. Turk. J. Chem. 2013, 37, 879–888.
Shao, L. J.; Chen, J.; He, L. Y.; Xing, G. Y.; Lv, W. X.; Chen, Z. N.; Qi, C. Z. Turk. J. Chem. 2012, 36, 700–708.
Beck, A.; Mangold, K. M.; Hanack, M. Chem. Ber. 1991, 124, 2315–2321.
Eberhardt, W.; Hanack, M. Synthesis 1997, 95–100.
Tau, P.; Nyokong, T. Dalton Trans. 2006, 34, 4482–4490.
Albrecht, M. Chem. Soc. Rev. 1998, 27, 281–288.
Albrecht, M.; Janser, I.; Runsink, J.; Raabe, G.; Weis, P.; Frohlich, R. Angew. Chem. Int. Ed. 2004, 43, 6662–6666.
Takami, T.; Clark, A.; Caldwell, R.; Mazur, U.; Hipps, K. W. Langmuir 2010, 26, 12709–12715.
Law, W. F.; Liu, R. C. W.; Jiang, J.; Ng, D. K. P. Inorg. Chim. Acta 1997, 256, 147–150.
Arslano˘glu, Y.; Hamuryudan, E. Dyes Pigments 2007, 75, 150–155.
Muranaka, A.; Okuda, M.; Kobayashi, N.; Somers, K.; Ceulemans, A. J. Am. Chem. Soc. 2004, 126, 4596–4604.
Palomares, E.; Martinez-Diaz, M. V.; Haque, S. A.; Torres, T.; Durrant, J. R. Chem. Commun. 2004, 2004, 2112–2113.
Koc, M.; Gurek, A. G.; Dumoulin, F.; Ahsen, V. Turk. J. Chem. 2012, 36, 493– 502.
Tarakci, D. K.; G¨urol, ˙I.; Ahsen, V. J. Porphyrins Phthalocyanines 2013, 17, 548–554.
Gurol, I.; Ahsen, V.; Bekaroglu, O. Dalton Trans. 1994, 4, 497–500.
Gurol, I.; Durmus, M.; Ahsen, V.; Nyokong, T. Dalton Trans. 2007, 2007, 3782–91.
Winter, G.; Heckmann, H.; Haisch P.; Eberhardt, W.; Hanack, M.; L¨uer, L.; Egelhaaf, H. J.; Oelkrung, D. J. Am. Chem. Soc. 1998, 120, 11663–11673.
Jpn. Kokai Tokkyo Koho (1991), 10 pp. CODEN:JKXXAF; JP3211532.
Barthel, M.; Dini, D.; Vagin, S.; Hanack, M. Eur. J. Org. Chem. 2002, 22, 3756–3762.
Kobayashi, N.; Muranaka, A. Chem. Commun. 2000, 19, 1855–1856.
Mthethwa, T. P.; Tuncel, S.; Durmu¸s, M.; Nyokong, T. Dalton Trans. 2013, 42, 4922–4930.
Maskasky, J. E.; Mooney, J. R.; Kenney, M. E. J. Am. Chem. Soc. 1972, 94, 2132–2133.
Aihara, K.; Urano, Y.; Higuchi, T.; Hirobe M. J. Chem. Soc., Perkin Trans. 2 1993, 2165–2170.
Godfrey, I. M.; Sargent, M. V.; Elix, J. A. J. Chem. Soc. Perkin Trans. 1 1974, 1353–1354.
Iakovidis, D.; Louis, S. N .S.; Rezmann, L. A.; Colagrande, F.; Nero, T. L.; Jackman, G. P.; Louis, W. J. Eur. J. Med. Chem. 1999, 34, 539–548.