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.

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.

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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.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
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