Synthesis and photophysical studies of a chlorin sterically designed to prevent self-aggregation

Synthesis and photophysical studies of a chlorin sterically designed to prevent self-aggregation

Assis, Francisco F. de; Souza, Juliana M. de; Assis, Beatriz H. K.; Brocksom, Timothy J.; Oliveira, Kleber T. de

Abstract:

Chlorins are obtained by reduction of one double bond at the β position of the porphyrin ring (Figure 1). The chlorins exhibit a strong absorption band around 660 nm, which suggests use in photodynamic therapy (PDT). Due to the extended conjugated core structure, they often suffer self-aggregation, which is a negative point for application in PDT. In this work, we have prepared a new chlorin derivative which is self-prevented from aggregation, by a 1,3- dipolar cycloaddition between a very activated porphyrin (dipolarophile) and a benzyl azomethine ylide. We have also performed some preliminary photophysical studies in order to evaluate its ability to act as a photosensitizer in PDT.

Chlorins are obtained by reduction of one double bond at the β position of the porphyrin ring (Figure 1). The chlorins exhibit a strong absorption band around 660 nm, which suggests use in photodynamic therapy (PDT). Due to the extended conjugated core structure, they often suffer self-aggregation, which is a negative point for application in PDT. In this work, we have prepared a new chlorin derivative which is self-prevented from aggregation, by a 1,3- dipolar cycloaddition between a very activated porphyrin (dipolarophile) and a benzyl azomethine ylide. We have also performed some preliminary photophysical studies in order to evaluate its ability to act as a photosensitizer in PDT.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013913102810

Referências bibliográficas

• [1] 1 Ethirajan, M.; Chen, Y.; Joshi, P.; Pandey, R. K. Chem. Soc. Rev. 2011,
• [2] 40, 340.
• [3] 2 de Assis, F. F.; de Souza, J. M.; Assis, B. H. K.; Brocksom, T. J.; de
• [4] Oliveira, K. T. Dyes and Pigments 2013, 98, 153.

Como citar:

Assis, Francisco F. de; Souza, Juliana M. de; Assis, Beatriz H. K.; Brocksom, Timothy J.; Oliveira, Kleber T. de; "Synthesis and photophysical studies of a chlorin sterically designed to prevent self-aggregation", p-220-220. 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_2013913102810