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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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Publication details

The article was received on 30 Dec 2016, accepted on 17 Jan 2017, published on 19 Jan 2017 and first published online on 19 Jan 2017


Article type: Research Article
DOI: 10.1039/C6QO00871B
Citation: Org. Chem. Front., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C6QO00871B

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