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Maeda C, Kurihara K, Masuda M, et al. Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins. Org Biomol Chem. 2015;13(46):11286-91doi: 10.1039/c5ob01824b.
Maeda, C., Kurihara, K., Masuda, M., & Yoshioka, N. (2015). Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins. Organic & biomolecular chemistry, 13(46), 11286-91. https://doi.org/10.1039/c5ob01824b
Maeda, Chihiro, et al. "Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins." Organic & biomolecular chemistry vol. 13,46 (2015): 11286-91. doi: https://doi.org/10.1039/c5ob01824b
Maeda C, Kurihara K, Masuda M, Yoshioka N. Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins. Org Biomol Chem. 2015 Dec 14;13(46):11286-91. doi: 10.1039/c5ob01824b. PMID: 26416478.
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Org Biomol Chem. 2015 Dec 14;13(46):11286-91. doi: 10.1039/c5ob01824b.

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

Organic & biomolecular chemistry

Chihiro Maeda, Kosuke Kurihara, Motoki Masuda, Naoki Yoshioka

Affiliations

  1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama 223-8522, Japan and Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan. [email protected].
  2. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama 223-8522, Japan.

PMID: 26416478 DOI: 10.1039/c5ob01824b

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.

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