Issue 46, 2015

Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins

Abstract

The synthesis and photophysical properties of cyano and ethynyl substituted carbazole-based porphyrins were investigated. The introduction of ethynyl groups induced red shifts, while that of cyano groups induced blue shifts of their absorption bands, which was supported by MO calculations. Ethylenedioxy-appended porphyrins were also prepared via a coupling reaction. The conjugated and electronic substituent effects on the photophysical properties of the carbazole-based porphyrins have been elucidated by using both experimental results and calculations. Among these porphyrins, the ethylenedioxy-appended selenaporphyrin displayed intensified and red-shifted absorption in the NIR region up to 1178 nm.

Graphical abstract: Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins

Supplementary files

Article information

Article type
Paper
Submitted
01 Sep 2015
Accepted
18 Sep 2015
First published
21 Sep 2015

Org. Biomol. Chem., 2015,13, 11286-11291

Author version available

Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins

C. Maeda, K. Kurihara, M. Masuda and N. Yoshioka, Org. Biomol. Chem., 2015, 13, 11286 DOI: 10.1039/C5OB01824B

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