Issue 41, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis of push–pull chromophores by the sequential [2 + 2] cycloaddition of 1-azulenylbutadiynes with tetracyanoethylene and tetrathiafulvalene†

Taku Shoji,*a   Shunji Ito,b   Tetsuo Okujimac  and  Noboru Moritad  

* Corresponding authors

a Department of Chemistry, Faculty School of Science, Shinshu University, Matsumoto 390-8621, Japan
E-mail: tshoji@shinshu-u.ac.jp
Fax: +81 263 2476
Tel: +81 263 2476

b Graduate School of Science and Technology, Hirosaki University, Hirosaki 036-8561, Japan

c Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

d Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

Abstract

Azulene-substituted butadiynes have been prepared by Cu-mediated cross- and homo-coupling reactions. The azulene-substituted butadiynes reacted with tetracyanoethylene in a formal [2 + 2] cycloaddition reaction to afford the corresponding 1,1,4,4-tetracyanobutadiene chromophores, in excellent yields. Further [2 + 2] cycloaddition with TTF and TCNE gave novel donor–acceptor chromophores and novel azulene-substituted 6,6-dicyanofulvene derivatives.

Graphical abstract: Synthesis of push–pull chromophores by the sequential [2 + 2] cycloaddition of 1-azulenylbutadiynes with tetracyanoethylene and tetrathiafulvalene

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Article information

DOI
https://doi.org/10.1039/C2OB26028J
Article type
Paper
Submitted
27 May 2012
Accepted
10 Aug 2012
First published
10 Aug 2012

Org. Biomol. Chem., 2012,10, 8308-8313

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Synthesis of push–pull chromophores by the sequential [2 + 2] cycloaddition of 1-azulenylbutadiynes with tetracyanoethylene and tetrathiafulvalene

T. Shoji, S. Ito, T. Okujima and N. Morita, Org. Biomol. Chem., 2012, 10, 8308 DOI: 10.1039/C2OB26028J

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