Selective thionation of naphtho[2,3-b]thiophene diimide: tuning of the optoelectronic properties and packing structure

Literature Information

Publication Date 2017-01-19
DOI 10.1039/C6QO00871B
Impact Factor 5.281
Authors

Masahiro Nakano, Kazuo Takimiya, Qichun Zhang


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Abstract

Naphtho[2,3-b]thiophene diimide (NTI) was found to be selectively thionated to afford naphtho[2,3-b]thiophene-4,9-dicarboxy-5,8-dithiocarboxydiimide (NTI-2S). By elucidating its electrochemical, optical, and structural properties, the effects of thionation on the molecular electronic structure and crystal structure were discussed. Although thionation can greatly lower the LUMO energy level and enhance the intermolecular interaction in the solid state, its chemical lability is a drawback as an organic semiconducting material.

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