Photoinduced Charge-Transfer State of 4-Carbazolyl-3-(trifluoromethyl)benzoic Acid: Photophysical Property and Application to Reduction of Carbon-Halogen Bonds as a Sensitizer

Ryosuke Matsubara; Toshiyuki Shimada; Yasuhiro Kobori; Tatsushi Yabuta; Toshiyuki Osakai; Masahiko Hayashi

doi:10.1002/asia.201600538

Photoinduced Charge-Transfer State of 4-Carbazolyl-3-(trifluoromethyl)benzoic Acid: Photophysical Property and Application to Reduction of Carbon-Halogen Bonds as a Sensitizer

Chem Asian J. 2016 Jul 20;11(14):2006-10. doi: 10.1002/asia.201600538. Epub 2016 Jul 1.

Authors

Ryosuke Matsubara¹, Toshiyuki Shimada², Yasuhiro Kobori³, Tatsushi Yabuta², Toshiyuki Osakai², Masahiko Hayashi²

Affiliations

¹ Department of Chemistry, Kobe University, Nada-ku, Kobe, Hyogo, 657-8501, Japan. matsubara.ryosuke@people.kobe-u.ac.jp.
² Department of Chemistry, Kobe University, Nada-ku, Kobe, Hyogo, 657-8501, Japan.
³ Department of Chemistry, Kobe University, Nada-ku, Kobe, Hyogo, 657-8501, Japan. ykobori@kitty.kobe-u.ac.jp.

PMID: 27305449
DOI: 10.1002/asia.201600538

Abstract

The photoinduced persistent intramolecular charge-transfer state of 4-carbazolyl-3-(trifluoromethyl)benzoic acid was confirmed. It showed a higher catalytic activity in terms of yield and selectivity in the photochemical reduction of alkyl halides compared to the parent carbazole. Even unactivated primary alkyl bromides could be reduced by this photocatalyst. The high catalytic activity is rationalized by considering the slower backward single-electron transfer owing to the spatial separation of the donor and acceptor subunits.

Keywords: charge transfer; photocatalysis; radicals; reduction; synthetic methods.