Synthesis of chiral porphyrins and their use in photochemical oxidation of carbonyl compounds

Autor:	Dorota Gryko, Ksenia Maximova, Katarzyna Rybicka-Jasińska, Dominika J. Walaszek, Agnieszka Lipke
Rok vydání:	2014
Předmět:	chemistry.chemical_compound chemistry Singlet oxygen Organocatalysis General Chemistry Proline Photochemistry Decomposition Peroxide Porphyrin Catalysis Conjugate
Zdroj:	Journal of Porphyrins and Phthalocyanines. 18:493-505
ISSN:	1099-1409 1088-4246
DOI:	10.1142/s1088424614500229
Popis:	A series of chiral A4, A2B2, and AB3 porphyrins bearing proline moieties at the meso-phenyl group has been synthesized. Photostability studies revealed that the number of L-proline units and their position on meso-phenyl rings strongly influence the decomposition rate of the catalyst. 5,10,15-Tris(mesityl)-20-(3-prolinanilidylphenyl)-21,23H-porphyrin is the most stable while porphyrin bearing four 3-prolinanilidylphenyl substituents completely decomposes in CHCl 3 within 3 h. Singlet oxygen quantum yields of the conjugates were determined by measuring the peak areas of the NIR emission of 1 O 2 (1280 nm) generated by these compounds and compared to that generated by the reference standard TPP. Selected porphyrins were tested as catalysts in the photooxidation of carbonyl compounds at the α-position.
Databáze:	OpenAIRE
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