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

Chihiro Maeda, Kosuke Kurihara, Motoki Masuda, Naoki Yoshioka

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)11286-11291
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number46
DOIs
Publication statusPublished - 2015 Sep 21

Fingerprint

carbazoles
Porphyrins
porphyrins
blue shift
red shift
Absorption spectra
absorption spectra
carbazole
synthesis
electronics

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins. / Maeda, Chihiro; Kurihara, Kosuke; Masuda, Motoki; Yoshioka, Naoki.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 46, 21.09.2015, p. 11286-11291.

Research output: Contribution to journalArticle

@article{254f61fed5b0406fb265d81d2e2b46eb,
title = "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.",
author = "Chihiro Maeda and Kosuke Kurihara and Motoki Masuda and Naoki Yoshioka",
year = "2015",
month = "9",
day = "21",
doi = "10.1039/c5ob01824b",
language = "English",
volume = "13",
pages = "11286--11291",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "46",

}

TY - JOUR

T1 - Effects of cyano, ethynyl and ethylenedioxy groups on the photophysical properties of carbazole-based porphyrins

AU - Maeda, Chihiro

AU - Kurihara, Kosuke

AU - Masuda, Motoki

AU - Yoshioka, Naoki

PY - 2015/9/21

Y1 - 2015/9/21

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84947711985&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84947711985&partnerID=8YFLogxK

U2 - 10.1039/c5ob01824b

DO - 10.1039/c5ob01824b

M3 - Article

AN - SCOPUS:84947711985

VL - 13

SP - 11286

EP - 11291

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 46

ER -