Premium
Synthesis and Characterization of Carbazole‐Linked Porphyrin Tweezers
Author(s) -
Chang Yi,
Michelin Clément,
Bucher Léo,
Desbois Nicolas,
Gros Claude P.,
Piant Sébastien,
Bolze Frédéric,
Fang Yuanyuan,
Jiang Xiaoqin,
Kadish Karl M.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501619
Subject(s) - carbazole , sonogashira coupling , quantum yield , photochemistry , tweezers , absorption (acoustics) , porphyrin , fluorescence , materials science , phosphorescence , chemistry , optics , organic chemistry , catalysis , palladium , physics , composite material
Herein the synthesis, spectroscopic characterization, two‐photon absorption and electrochemical properties of 3,6‐disubstituted carbazole tweezers is reported. A dimer resulting from a Glaser homocoupling was isolated during a Sonogashira coupling reaction between a diethynyl‐carbazole spacer and a 5‐bromo‐triarylporphyrin and the properties of this original compound were compared with the 3,6‐disubstituted carbazole bisporphyrin tweezers. The dyads reported herein present a two‐photon absorption maximum at 920 nm with two‐photon absorption cross‐section in the 1200 GM range. Despite a strong linear absorption in the Soret region and moderate fluorescence quantum yield, they both lead to a high brightness reaching 30 000 M −1 cm −1 .