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Selective thionation of naphtho[2,3-b]thiophene diimide: tuning of the optoelectronic properties and packing structure†
Kazuo
Takimiya 
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and
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and
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](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C6QO00871B&imageInfo.ImageIdentifier.Year=2017)
- This article is part of the themed collection: Novel π-electron molecular scaffolds
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