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
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.
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.
