Cai Z, Zhang H, Geng H, Liu Z, * Yang S, Luo H, Jiang L, Peng Q, Zhang G, Chen J,
Yi Y, Hu W, Zhang D. * Beijing National Laboratory for Molecular Sciences, P. R. China
Thiepin-Fused Heteroacenes: Simple Synthesis, Unusual Structure, and Semiconductors
with Less Anisotropic Behavior.
Chem. Eur. J. 2013;
19: 14573-14580
Key words
fused ring systems - thiepins - heteroacenes
Significance
Polycyclic aromatic hydrocarbons with heteroatom substitution are attractive materials
for semiconductor applications. The authors present the efficient installation of
a thiepin unit onto easily accessible DIDT (C.-H. Chen, Y.-J. Cheng, M. Dubosc, C.-H.
Hsieh, C.-C. Chu, C.-S. Hsu Chem. Asian J. 2010, 5, 2483). In this one-pot synthesis, DIDT was deprotonated with potassium tert-butoxide, reacted with carbon disulfide, and quenched with methyl iodide or hexyl
bromide. The fused thiepins were obtained in 90% and 80% yield.
Comment
HOMO and LUMO energies were determined by cyclic voltammetry (–5.35 eV and –3.26
eV, respectively, regardless of the alkyl chain). Both compounds exhibited typical
p-type semiconducting behavior with hole mobilities up to 1.0 x 10–2 cm2 V–1 s–1. Thin films were further characterized by AFM and XRD. Crystal structures were obtained
for both compounds and showed multiple S…S contacts.
