Synthesis of phthalocyanines functionalized by 4-fluorophenoxy moieties and their linear optical properties

Cheolsoo Jung; Byeongjin Beak; Masa-aki Kakimoto

Journal of Industrial and Engineering Chemistry, Vol.20, No.1, 234-237, January, 2014

DOI10.1016/j.jiec.2013.03.042 Export Citation

Synthesis of phthalocyanines functionalized by 4-fluorophenoxy moieties and their linear optical properties

Cheolsoo Jung^†, Byeongjin Beak, and Masa-aki Kakimoto¹

Department of Chemical Engineering, University of Seoul, Seoul 130-743, Republic of Korea
¹Department of Organic and Polymeric Materials, Tokyo Institute of Technology, Tokyo 152-8552, Japan

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Four kinds of phthalocyanines with 4-fluorophenoxy group (H2Pc, CuPc, Li2Pc, and FePc) are synthesized by the microwave-assisted method under 15 min. The synthesized phthalocyanines have good solubility in aprotic polar solvents and do not form any new aggregation state with a concentration increase. The phthalocyanine coordinated with Li+ ion has a more stable and stronger absorption property in aprotic polar solvents than the phthalocyanine with Cu2+ or Fe2+ ion. The phthalocyanine coordinated with Fe2+ ion is more subject to H-aggregation than other phthalocyanines, especially in polar solvents.

Keywords:4-Fluorophenoxy phthalocyanine (Pc);Microwave-assisted synthesis;Aggregation;UV-vis absorption;Solubility

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[1] Zhou R, Josse F, Gopel W, Ozturk ZZ, Bekaroglu O, Applied Organometallic Chemistry., 10, 557 (1996)

[2] Legin A, Makarychev-Mikhailov S, Goryacheva O, Kirsanov D, Vlasov Y, Analytica Chimica Acta., 457, 297 (2002)

[3] Brinkmann H, Kelting C, Makarov S, Tsaryova O, Schnurpfeil G, Wo¨ hrle D, Schlettwein D, Physica Status Solidi (A)., 205, 409 (2008)

[4] Papageorgiou N, Salomon E, Angot T, Layet JM, Giovanelli L, Lay GL, Progress in Surface Science., 77, 139 (2005)

[5] Griffiths J, Cruse-Sawyer J, Wood SR, Schofield J, Brown SB, Dixon B, Journal of Photochemistry and Photobiology B: Biology., 24, 195 (1994)

[6] Sakamoto K, Kato T, Ohno-Okomura E, Watanabe M, Cook MJ, 64, 63 (2005)

[7] Redmond RW, Gamlin JN, Photochemistry and Photobiology., 70, 391 (1999)

[8] Sharman WM, Allen CM, Van Lier JE, Drug Discovery Today., 4, 507 (1999)

[9] Claessens C, Hahn U, Torres T, The Chemical Record., 8, 75 (2008)

[10] Murray SG, Hartley FR, Chemical Reviews., 81, 365 (1981)

[11] Chen Y, Hanack M, Blau WJ, Dini D, Liu Y, Lin Y, Bai JR, J. Mater. Sci., 41(8), 2169 (2006)

[12] Kantekin H, Dilber G, Bıyıklıoglu Z, Journal of Organometallic Chemistry., 693, 1038 (2008)

[13] Liu M, Tai C, Wang W, Chen J, Hu AT, Wei T, Journal of Organometallic Chemistry., 689, 1078 (2004)

[14] Karaoglan GK, Gumrukcu G, Koca A, Gul A, Dyes and Pigments., 88, 247 (2011)

[15] Yabas E, Sulu M, Saydam S, Dumludag F, Salih B, Bekaroglu O, Inorganica Chimica Acta., 365, 340 (2011)

[16] Leznoff CC, Lever ABP, Phthalocyanines: Properties and Applications, vol. 1, VCH Publisher, New York (1989)

[17] Dominguez DD, Snow AW, Shirk JS, Pong RGS, Journal of Porphyrins and Phthalocyanines., 5, 582 (2001)

[18] Kroon JM, Koehorst RBM, Van Dijk M, Sanders GM, Sudholter EJR, Journal of Materials Chemistry., 7, 615 (1997)

[19] Ogunsipe A, Nyokong T, Journal of Molecular Structure., 689, 89 (2004)

[20] Arnbjerg J, Johnsen M, Nielsen CB, Jorgensen M, Ogilby PR, J. Phys. Chem. A, 111(21), 4573 (2007)