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Molecules 2015, 20(8), 13575-13590; doi:10.3390/molecules200813575

Photochemical and Photophysical Properties of Phthalocyanines Modified with Optically Active Alcohols

Centro de Ciências Naturais e Humanas—CCNH, Universidade Federal do ABC—UFABC, Avenida dos Estados, 5005, Bairro Bangu, Santo André—SP 09210-190, Brasil
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Author to whom correspondence should be addressed.
Academic Editor: Giuseppe Mele
Received: 26 May 2015 / Accepted: 2 July 2015 / Published: 24 July 2015
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)
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Abstract

Three phthalocyanine derivatives were synthesized and characterized: one modified with a racemic mixture of 1-(4-bromophenyl)ethanol and two other macrocycles modified with each one of the enantioenriched isomers (R)-1-(4-bromophenyl)ethanol and (S)-1-(4-bromophenyl)ethanol. The compounds were characterized by 1H-NMR spectroscopy, mass spectrometry, UV-Vis absorption, and excitation and emission spectra. Additionally, partition coefficient values and the quantum yield of the generation of oxygen reactive species were determined. Interestingly, the phthalocyanine containing a (R)-1-(4-bromophenyl)ethoxy moiety showed higher quantum yield of reactive oxygen species generation than other compounds under the same conditions. In addition, the obtained fluorescence microscopy and cell viability results have shown that these phthalocyanines have different interactions with mammary MCF-7 cells. Therefore, our results indicate that the photochemical and biological properties of phthalocyanines with chiral ligands should be evaluated separately for each enantiomeric species. View Full-Text
Keywords: chiral phthalocyanines; enzymatic resolution; photodynamic therapy; photosensitizer; dyes chiral phthalocyanines; enzymatic resolution; photodynamic therapy; photosensitizer; dyes
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ramos, A.A.; Nascimento, F.B.; de Souza, T.F.M.; Omori, A.T.; Manieri, T.M.; Cerchiaro, G.; Ribeiro, A.O. Photochemical and Photophysical Properties of Phthalocyanines Modified with Optically Active Alcohols. Molecules 2015, 20, 13575-13590.

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