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SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES

Year 2013, Volume: 14 Issue: 2, 135 - 142, 01.11.2013

Abstract

Symmetrically substituted phthalocyanine derivatives have been synthesized from the reaction of anhydrous metal salts of titanium with 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio) phthalonitrile (3). 4-phthalonitrile (1) and 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthiol) (2) in dry dimethylformamide as solvent and using K2CO3 as base via the common method of nucleophilic substitution of an activated nitro group in an aromatic ring. The compound 3,9,17,23-bis[ethane-1,1-p-phenol-2,2-p-phenokxy]phthalocyaninatocobalt (II) (FlTi2CoPc) (4) was reacted with the compound 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio) phthalocyaninatotinanium (IV) (5), which is similar to those synthesized in the past, to syhthesize a new derivative containing three phthalocyanines 3,9,17,23-bis[ethane-1,1-p-(4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio) phthalocyaninatotinanium (IV))-2,2-p-phenokxy]phthalocyaninatocobalt (II) (FlTi2CoPc)  (6). The synthesized molecules have been characterized by 19F NMR, HETCOR, MALDI-TOFF, UV-Vis and IR spectroscopies.

References

  • Arslanoglu, Y., Sevim, A.M., Hamuryudan, E., Gul, A., (2006). Near-IR Absorbing Phthalocyanines, Dyes and Pigments, 68, 129-132.
  • Bıyıkoğlu, Z., (2013). Water-soluble Axially Disubstituted Non-aggregated Silicon Phthalocyanines and Their Electrochemical Properties. Dyes and Pigments, 99, 59–66.
  • Wilfred L.F. Armarego and Christina Li Lin
  • Ceyhan, T., Altındal, A., Erbil, M. K., Bekaroğlu, Ö., (2006). Synthesis, Characterization, Conduction and Gas Sensing Properties of Novel Multinuclear Metallo Phthalocyanines (Zn, Co) With Alkylthio Substituents. Polyhedron, 25, ,737–746.
  • Yılmaz, Ö., (2006), Yeni Tip Okso- Titanyum
  • Gullotti, M., Pasini, A., (1975). Schiff Base Complexes of Oxocatiohs. Part III*. Oxotitanium(IV) Complexes with Tetradentate Optically Active Schiff Bases. Inorganica Chimica Acta, 15, 129- 136.
  • Jin, L., Chen, D., (2012). Enhancement in Photovoltaic Performance of Phthalocyanine-sensitized Solar cells by Attapulgite Nanoparticles. Electrochimica Acta, 72, 40–45.
  • Kobayashi, S., (2002). Dimers, Trimers and Oligomers of Phthalocyanines and Related Compounds, Coordination Chemistry Reviews, 227, 129-152.
  • Lokesh,K. S., Adriaens, A., (2013). Synthesis and Characterization of Tetra-Substituted Palladium Phthalocyanine Complexes. Dyes and Pigments, 96, 1, 269-277.
  • Moussaron, A., Arnoux, P., Vanderesse, R., Sibille, E., (2013). Lipophilic Phthalocyanines for Their Potential Interest in Photodynamic Therapy: Synthesis and photo-physical properties. Tetrahedron, 69, 47, 10116–10122.
  • Shumov,Y. S., Heyrovský, M., (1975). The Relation Between Catalytic and Photoelectro-chemical Properties of Phthalocyanine Films. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 65, 1, 469– 471.
  • Simon, J.; Andre, J.J. (1985). Molecular semiconductors; Chapter 3, 73-149, Springer; Berlin. Chai, (2009), Purification of Laboratory Chemicals (Sixth Edition), ISBN: 978-1- 85617-567-8, Elsevier Inc., Oxford OX2 8DP, UK). (IV) Ftalosiyaninlerin Sentezi ve Karakterizasyonu, Yüksek Lisans Tezi, T.C. Gebze Yüksek Teknoloji Enstitüsü Mühendislik ve Fen Bilimleri Enstitüsü.
  • Zakharov, A.V., Girichev, G. V., (2008). Theoretical Study of The Structure, Vibrational Spectra, and Electronic Spectra of Oxotitanium Porphyrin, Octamethylporphyrin, Porphyrazine, and Phthalocyanine Complexes. Journal of Molecular Structure: THEOCHEM, Volume 851, 1–3,183-196.
  • Zugle, R., Nyokong, T., (2013). Zinc(II) 2,9,16,23-Tetrakis[4-(N-Methylpyridyloxy)]- Phthalocyanine Anchored on An Electrospun Polysulfone Polymer Fiber: Application for Photosensitized Conversion of Methyl Orange. Journal of Molecular Catalysis A: Chemical, 366, 247-253.

(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADEKAFLORODESİLL) (METİL) SULFAN SÜBSTİTÜE TİTANYUM FTALOSİYANİN TÜREVLERİNİN SENTEZİ VE KARAKTERİZASYONU

Year 2013, Volume: 14 Issue: 2, 135 - 142, 01.11.2013

Abstract

References

  • Arslanoglu, Y., Sevim, A.M., Hamuryudan, E., Gul, A., (2006). Near-IR Absorbing Phthalocyanines, Dyes and Pigments, 68, 129-132.
  • Bıyıkoğlu, Z., (2013). Water-soluble Axially Disubstituted Non-aggregated Silicon Phthalocyanines and Their Electrochemical Properties. Dyes and Pigments, 99, 59–66.
  • Wilfred L.F. Armarego and Christina Li Lin
  • Ceyhan, T., Altındal, A., Erbil, M. K., Bekaroğlu, Ö., (2006). Synthesis, Characterization, Conduction and Gas Sensing Properties of Novel Multinuclear Metallo Phthalocyanines (Zn, Co) With Alkylthio Substituents. Polyhedron, 25, ,737–746.
  • Yılmaz, Ö., (2006), Yeni Tip Okso- Titanyum
  • Gullotti, M., Pasini, A., (1975). Schiff Base Complexes of Oxocatiohs. Part III*. Oxotitanium(IV) Complexes with Tetradentate Optically Active Schiff Bases. Inorganica Chimica Acta, 15, 129- 136.
  • Jin, L., Chen, D., (2012). Enhancement in Photovoltaic Performance of Phthalocyanine-sensitized Solar cells by Attapulgite Nanoparticles. Electrochimica Acta, 72, 40–45.
  • Kobayashi, S., (2002). Dimers, Trimers and Oligomers of Phthalocyanines and Related Compounds, Coordination Chemistry Reviews, 227, 129-152.
  • Lokesh,K. S., Adriaens, A., (2013). Synthesis and Characterization of Tetra-Substituted Palladium Phthalocyanine Complexes. Dyes and Pigments, 96, 1, 269-277.
  • Moussaron, A., Arnoux, P., Vanderesse, R., Sibille, E., (2013). Lipophilic Phthalocyanines for Their Potential Interest in Photodynamic Therapy: Synthesis and photo-physical properties. Tetrahedron, 69, 47, 10116–10122.
  • Shumov,Y. S., Heyrovský, M., (1975). The Relation Between Catalytic and Photoelectro-chemical Properties of Phthalocyanine Films. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 65, 1, 469– 471.
  • Simon, J.; Andre, J.J. (1985). Molecular semiconductors; Chapter 3, 73-149, Springer; Berlin. Chai, (2009), Purification of Laboratory Chemicals (Sixth Edition), ISBN: 978-1- 85617-567-8, Elsevier Inc., Oxford OX2 8DP, UK). (IV) Ftalosiyaninlerin Sentezi ve Karakterizasyonu, Yüksek Lisans Tezi, T.C. Gebze Yüksek Teknoloji Enstitüsü Mühendislik ve Fen Bilimleri Enstitüsü.
  • Zakharov, A.V., Girichev, G. V., (2008). Theoretical Study of The Structure, Vibrational Spectra, and Electronic Spectra of Oxotitanium Porphyrin, Octamethylporphyrin, Porphyrazine, and Phthalocyanine Complexes. Journal of Molecular Structure: THEOCHEM, Volume 851, 1–3,183-196.
  • Zugle, R., Nyokong, T., (2013). Zinc(II) 2,9,16,23-Tetrakis[4-(N-Methylpyridyloxy)]- Phthalocyanine Anchored on An Electrospun Polysulfone Polymer Fiber: Application for Photosensitized Conversion of Methyl Orange. Journal of Molecular Catalysis A: Chemical, 366, 247-253.
There are 14 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Dilek Elmalı

Gürol Demirel This is me

Publication Date November 1, 2013
Published in Issue Year 2013 Volume: 14 Issue: 2

Cite

APA Elmalı, D., & Demirel, G. (2013). SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 14(2), 135-142.
AMA Elmalı D, Demirel G. SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES. AUJST-A. November 2013;14(2):135-142.
Chicago Elmalı, Dilek, and Gürol Demirel. “SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 14, no. 2 (November 2013): 135-42.
EndNote Elmalı D, Demirel G (November 1, 2013) SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 14 2 135–142.
IEEE D. Elmalı and G. Demirel, “SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES”, AUJST-A, vol. 14, no. 2, pp. 135–142, 2013.
ISNAD Elmalı, Dilek - Demirel, Gürol. “SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 14/2 (November 2013), 135-142.
JAMA Elmalı D, Demirel G. SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES. AUJST-A. 2013;14:135–142.
MLA Elmalı, Dilek and Gürol Demirel. “SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, vol. 14, no. 2, 2013, pp. 135-42.
Vancouver Elmalı D, Demirel G. SYNTHESIS AND CHARACTERIZATION OF SOME (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-HEPTADECAFLUORODECYL) (METHYL) SULFANE SUBSTITUTED TITANIUM PHTHALOCYANINE DERIVATIVES. AUJST-A. 2013;14(2):135-42.