TY - JOUR
T1 - Synthesis of 2-Azulenyltetrathiafulvalenes by Palladium-Catalyzed Direct Arylation of 2-Chloroazulenes with Tetrathiafulvalene and Their Optical and Electrochemical Properties
AU - Shoji, Taku
AU - Araki, Takanori
AU - Sugiyama, Shuhei
AU - Ohta, Akira
AU - Sekiguchi, Ryuta
AU - Ito, Shunji
AU - Okujima, Tetsuo
AU - Toyota, Kozo
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant Number 25810019 (TS), JSPS KAKENHI Grant Number 16K05679, and JSPS KAKENHI Grant Number 26410052 (TO), and also by a research grant from the Faculty of Science, Shinshu University.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/2/3
Y1 - 2017/2/3
N2 - Tetrathiafulvalene (TTF) derivatives with 2-azulenyl substituents 5-11 were prepared by the palladium-catalyzed direct arylation reaction of 2-chloroazulenes with TTF in good yield. Photophysical properties of these compounds were investigated by UV-vis spectroscopy and theoretical calculations. Redox behavior of the novel azulene-substituted TTFs was examined by using cyclic voltammetry and differential pulse voltammetry, which revealed their multistep electrochemical oxidation and/or reduction properties. Moreover, these TTF derivatives showed significant spectral change in the visible region under the redox conditions.
AB - Tetrathiafulvalene (TTF) derivatives with 2-azulenyl substituents 5-11 were prepared by the palladium-catalyzed direct arylation reaction of 2-chloroazulenes with TTF in good yield. Photophysical properties of these compounds were investigated by UV-vis spectroscopy and theoretical calculations. Redox behavior of the novel azulene-substituted TTFs was examined by using cyclic voltammetry and differential pulse voltammetry, which revealed their multistep electrochemical oxidation and/or reduction properties. Moreover, these TTF derivatives showed significant spectral change in the visible region under the redox conditions.
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U2 - 10.1021/acs.joc.6b02818
DO - 10.1021/acs.joc.6b02818
M3 - Article
C2 - 28094947
AN - SCOPUS:85011372869
SN - 0022-3263
VL - 82
SP - 1657
EP - 1665
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 3
ER -