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Issue 5, 2017
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Selective thionation of naphtho[2,3-b]thiophene diimide: tuning of the optoelectronic properties and packing structure

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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.

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

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Article information


Submitted
30 Dec 2016
Accepted
17 Jan 2017
First published
19 Jan 2017

Org. Chem. Front., 2017,4, 704-710
Article type
Research Article

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

W. Chen, M. Nakano, K. Takimiya and Q. Zhang, Org. Chem. Front., 2017, 4, 704
DOI: 10.1039/C6QO00871B

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