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

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.

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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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, 3632.
• [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-70-70. 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_201391291318