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Synfacts 2014; 10(1): 0029
DOI: 10.1055/s-0033-1340393
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Thiepin-Fused Heteroacenes

Contributor(s):
Timothy M. Swager
,
Georgios Markopoulos
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
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Publication History

Publication Date:
13 December 2013 (online)

 
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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.


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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.


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