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Synfacts 2015; 11(1): 0039
DOI: 10.1055/s-0034-1379671
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A High Cyano Content Indacene as a Stable Organic Electron Acceptor

Contributor(s):
Timothy M. Swager
,
Elizabeth S. Sterner
Endo Y, Hasegawa M, * Matsui T, Yagi H, Hino S, Mazaki Y. * Kitasato University, Sagamihara, and Ehime University, Matsuyama, Japan
Synthesis and Electronic Structure of Dicyanofulvene-Fused Electron Accepting Molecule Based on a 1,5-Dihydro-s-Indacene Framework.

Org. Lett. 2014;
16: 5608-5611
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

electron acceptor - indacenes - nitriles

Significance

The authors used rational design to target the reported structure, compound 1. The indacene framework was stabilized by the high degree of cyano functionalization without compromising ease of reduction, which has been an issue with indacenes stabilized by benzannulation. The high cyano content also lowered the LUMO to –5.8 eV. Cyclic voltammetry shows four reversible single electron transfers, and UV/Vis shows a band gap of ~1.9 eV.


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Comment

The synthesis began from a previously reported compound (C. Adams et al. Inorg. Chim. Acta 2011, 366, 44), produced 330 mg of pure 3a, and should be scalable. Compound 3a was found to be generally stable both as a solid and in solution, possibly due to the low-lying LUMO.


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