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Synthesis and Properties of Azulene‐Substituted Donor–Acceptor Chromophores Connected by Arylamine Cores
Author(s) -
Shoji Taku,
Shimomura Erika,
Maruyama Mitsuhisa,
Maruyama Akifumi,
Ito Shunji,
Okujima Tetsuo,
Toyota Kozo,
Morita Noboru
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301006
Subject(s) - azulene , chemistry , tetracyanoethylene , chromophore , cyclic voltammetry , photochemistry , differential pulse voltammetry , cycloaddition , intramolecular force , acceptor , redox , electrochemistry , tetracyanoquinodimethane , spectroscopy , organic chemistry , molecule , electrode , catalysis , physics , condensed matter physics , quantum mechanics
1‐Ethynylazulenes connected by several arylamine cores reacted with tetracyanoethylene (TCNE) and 7,7,8,8‐tetracyanoquinodimethane (TCNQ) in a formal [2+2] cycloaddition–cycloreversion reaction to afford the corresponding tetracyanobutadiene (TCBD) and dicyanoquinodimethane (DCNQ) chromophores, respectively, in excellent yields. The intramolecular charge‐transfer (ICT) characters between the donor (azulene and arylamine cores) and acceptor (TCBD and DCNQ units) moieties were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behavior of the new TCBD and DCNQ derivatives was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties. Moreover, significant color changes were observed by visible spectroscopy under the electrochemical reduction conditions.