Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

2,5-Di(trimethylsilanyl)dithieno[2,3- b :3′,2′- d ]thiophene ((TMS) 2 - bb - DTT ), 2,5-di(trimethylsilanyl)diseleno[2,3- b :3′,2′- d ]thiophene ((TMS) 2 - bb - DST ), and 2,5-di(trimethylsilanyl)diseleno[2,3- b :3′,2′- d ] selenophene ((TMS) 2 - bb - DSS ) were used as starting materials to synthes...

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Published in:Beilstein journal of organic chemistry 2022-07, Vol.18 (1), p.809-817
Main Authors: Wang, Mengjie, Dang, Lanping, Xu, Wan, Ma, Zhiying, Shao, Liuliu, Wang, Guangxia, Li, Chunli, Wang, Hua
Format: Article
Language:English
Subjects:
Chemistry
crystal structure
Dithiothreitol
double helicene
Hydrocarbons
Letter
regioselective synthesis
Selenium
selenophene
Sulfur
thiophene
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Summary:2,5-Di(trimethylsilanyl)dithieno[2,3- b :3′,2′- d ]thiophene ((TMS) 2 - bb - DTT ), 2,5-di(trimethylsilanyl)diseleno[2,3- b :3′,2′- d ]thiophene ((TMS) 2 - bb - DST ), and 2,5-di(trimethylsilanyl)diseleno[2,3- b :3′,2′- d ] selenophene ((TMS) 2 - bb - DSS ) were used as starting materials to synthesize three S-shaped double helicenes (i.e., DH - 1 , DH - 2 , and DH - 3 ) through monobromination, formylation, the Wittig reaction, and double oxidative photocyclization. The photocyclization was a highly regioselective process. The molecular structures of DH - 1 and DH - 2 were confirmed by X-ray single-crystal analysis. Multiple intermolecular interactions, such as C–S, C–Se, S–S, S–Se, and Se–Se, were observed in the crystal packing structures of these compounds. Spectroscopic results and our previous work showed that the combination of molecular structure change and heteroatom replacement from S to Se could precisely modulate molecular energy levels.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.18.81