Cross-coupling reactions as a strategy for Naphthalocyanine synthesis

Cross-coupling reactions as a strategy for Naphthalocyanine synthesis

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

Abstract:

Naphthalocyanines are a third order class of photosensitizers with a highly -conjugated system, allowing absorption in near-infrared spectra. Photosensitizers with absorption over 700 nm are useful for applications in many areas such as photodynamic therapy (PDT), solar cells, semiconductors, catalysis and others. Due to these potential applications, methodologies for naphthalocyanine synthesis start from the traditional cyclotetramerization of building blocks such as naphthalonitriles and naphthalimides. This sometimes limits functionalizations, and results in poor yields due to the drastic conditions required. Therefore, the development of new methods which permit structural modifications, and also the enhancment of the photophysical and photochemical properties, are under study in our research group. Herein we propose to obtain naphthalocyanines by cross coupling reactions of halogenated phthalocyanines and vinylic esters, followed by onepot electrocyclic reactions.

Naphthalocyanines are a third order class of photosensitizers with a highly -conjugated system, allowing absorption in near-infrared spectra. Photosensitizers with absorption over 700 nm are useful for applications in many areas such as photodynamic therapy (PDT), solar cells, semiconductors, catalysis and others. Due to these potential applications, methodologies for naphthalocyanine synthesis start from the traditional cyclotetramerization of building blocks such as naphthalonitriles and naphthalimides. This sometimes limits functionalizations, and results in poor yields due to the drastic conditions required. Therefore, the development of new methods which permit structural modifications, and also the enhancment of the photophysical and photochemical properties, are under study in our research group. Herein we propose to obtain naphthalocyanines by cross coupling reactions of halogenated phthalocyanines and vinylic esters, followed by onepot electrocyclic reactions.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013911161227

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Como citar:

Gobo, Nicholas R. S.; Brocksom, Timothy J.; Oliveira, Kleber T. de; "Cross-coupling reactions as a strategy for Naphthalocyanine synthesis", p-207-207. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013911161227