Synthesis of substituted phthalonitrile building blocks for the preparation of non-aggregating phthalocyanines

Synthesis of substituted phthalonitrile building blocks for the preparation of non-aggregating phthalocyanines

Gobo, Nicholas R. S.; Brocksom, Timothy J.; Oliveira, Kleber T. de

Abstract:

Phthalocyanines since their discovery, have been the focus of much research because of wide applications in different areas of science, namely photodynamic therapy (PDT), semiconductors, liquid crystals, photovoltaic and solar cells. The most important challenge in phthalocyanine synthesis is the production of a macrocycle with low aggregation and adequate photophysical proporieties. The introduction of bulky groups on the periphery of the phthalocyanines core structure has been used to avoid aggregation, and has yielded promising biological activities. In this work, we describe our first attempts to synthesize a series of substituted phthalonitrile building blocks, using the Diels-Alder reaction between 3,4-substituted thiophene-1,1-dioxide and fumaronitrile as key step. As is well known, phthalonitriles are the main building blocks to synthesize phthalocyanines. To start the development of this methodology, the 3,4-ditertbutyl- thiophene (5) was prepared (Scheme 1).

Phthalocyanines since their discovery, have been the focus of much research because of wide applications in different areas of science, namely photodynamic therapy (PDT), semiconductors, liquid crystals, photovoltaic and solar cells. The most important challenge in phthalocyanine synthesis is the production of a macrocycle with low aggregation and adequate photophysical proporieties. The introduction of bulky groups on the periphery of the phthalocyanines core structure has been used to avoid aggregation, and has yielded promising biological activities. In this work, we describe our first attempts to synthesize a series of substituted phthalonitrile building blocks, using the Diels-Alder reaction between 3,4-substituted thiophene-1,1-dioxide and fumaronitrile as key step. As is well known, phthalonitriles are the main building blocks to synthesize phthalocyanines. To start the development of this methodology, the 3,4-ditertbutyl- thiophene (5) was prepared (Scheme 1).

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DOI: 10.5151/chempro-14bmos-R0198-1

Referências bibliográficas

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• [3] 3 de Oliveira, K. T.; de Assis, F. F.; Ribeiro, A. O.; Neri, C. R.; Fernandes, A. U.; Baptista, M. S.; Lopes, N. P.; Serra, O. A.; Iamamoto, I. J. Org. Chem. 2009, 74, 7962-7965.
• [4] 4 Nakayama, J.; Hasemi, R.; Yoshimura, K.; Sugihara, Y.; Yamaoka, S.; Nakamura, N. J. Org. Chem., 1998, 63, 4912.

Como citar:

Gobo, Nicholas R. S.; Brocksom, Timothy J.; Oliveira, Kleber T. de; "Synthesis of substituted phthalonitrile building blocks for the preparation of non-aggregating phthalocyanines", p-198-198. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0198-1