Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Letter
Time-integrated One-pot Synthesis, X-ray Structure, and Redox Properties of Electrochromic 1,3-Diarylisobenzofurans
Toshiyuki HamuraRyosuke NakayamaKeisuke HanadaYuto SakanoRyo KatoonoKenshu FujiwaraTakanori Suzuki
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2013 Volume 42 Issue 10 Pages 1244-1246

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Abstract

1,3-Bis[4-(dimethylamino)phenyl]isobenzofuran (1a) and a derivative were efficiently prepared through a sequence of reactions in a single batch reactor (time integration). The o-quinodimethane-type π-conjugation in 1a was confirmed by bond alternation determined by a low-temperature X-ray analysis. Brightly colored heterocycle 1a undergoes reversible two-stage one-electron oxidation, and electrolysis of 1a induces a vivid change in UV–vis–NIR absorptions exhibiting several isosbestic points (electrochromism).

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© 2013 The Chemical Society of Japan
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