Thiophene‐Fused 1,4‐Thiaborins: Synthesis, Structures and Properties

• Published in: Asian journal of organic chemistry Vol. 6; no. 5; pp. 496 - 502
• Main Authors: Yan, Yanan, Sun, Zhe, Li, Chenglong, Zhang, Jinyun, Lv, Lei, Liu, Xuguang, Liu, Xiujie
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 01-05-2017
• Subjects: 1,4-thiaborins; Aromaticity; boron; Crystallography; heterocycles; Organic chemistry; Pi-electrons; thiophene; Thiophenes
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.201700063

Two isomeric 1,4‐thiaborin derivatives fused by two thiophene rings (dithieno‐1,4‐thiaborins, DTTBs) were synthesized in two steps from commercially available materials, and their structures were confirmed by X‐ray crystallographic analysis. DTTBs 1 and 2 showed excellent stability towards air and moisture. Theoretical calculations revealed that the fusion of thiophenes enhanced the aromaticity of the centered 1,4‐thiaborins compared to their corresponding dibenzothiaborins. Furthermore, DTTBs 1 and 2 could be further functionalized by metalation followed by addition of electrophile. DTTBs are promising platforms upon which it is possible to build the next generation of organoboron π‐electron materials.
Aroma(ticity) therapy: Two dithieno‐1,4‐thiaborins have been synthesized and characterized. Their photophysical properties have been investigated by experimental and theoretical calculations, showing that they could be promising platforms for future π‐electron materials.