Dezembro 2013 vol. 1 num. 2 - Brazilian Meeting on Organic Synthesis 2013

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1,3-Dipolar Cycloaddition Reactions of meso-Tetra(2’- thienyl)porphyrins with a Nitrile Oxide

Momo, Patrícia B. ; Ayres, Ricardo B. ; Brocksom, Timothy J. ; Oliveira, Kleber T. de ;

Abstract:

Tetrathienylporphyrins have gained much interest recently due to their remarkable photophysical and electrochemical properties. Derivatives such as chlorins, isobacteriochlorins and bacteriochlorins, can be synthesized by reduction with diimide or para-toluenesulfonylhydrazide, as well as oxidation with OsO4, and Diels-Alder reactions and 1,3-dipolar cycloadditions, on the peripheral double bonds of the pyrrolic rings. Chlorins and bacteriochlorins have been used in several scientific areas, especially in medicine. We have now explored the 1,3-dipolar cycloaddition of 2,6-dichlorobenzonitrile oxide with tetra(2’-thienyl)porphyrins 1a-d (Scheme 1). We observed that tetra(2’-thienyl)porphyrins can react with the dipolarophile yielding chlorins and bacteriochlorins. These new compounds are candidates for use in photodynamic therapy (PDT) and solar cells studies.

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Palavras-chave: 1,3-dipolar cycloaddition, chlorins, bacteriochlorins,

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DOI: 10.5151/chempro-15bmos-BMOS2013_201391291318

Referências bibliográficas
  • [1] 1 Boyle, M. N.; Rochford, J.; Pryce, M. T. Coord. Chem. Rev. 2010, 254, 7.
  • [2] 2 Xingang, L.; Yaqing, F.; Xiaofen, H.; Xianggao, L. Synthesis, 2005, 20, 363
  • [3] 3Li, X.; Zhuang, J.; Li, Y.; Liu, H.; Wang, S.; Zhu, D. Tetrahedron Letters, 2005, 46, 1555.
Como citar:

Momo, Patrícia B.; Ayres, Ricardo B.; Brocksom, Timothy J.; Oliveira, Kleber T. de; "1,3-Dipolar Cycloaddition Reactions of meso-Tetra(2’- thienyl)porphyrins with a Nitrile Oxide", p. 70 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-15bmos-BMOS2013_201391291318

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