Syntheses and Crystal Structures of Fused Thiophenes: [7]Helicene and Double Helicene, a D2-Symmetric Dimer of 3,3′-Bis(dithieno[2,3-b:3′,2′-d]thiophene)

Syntheses and Crystal Structures of Fused Thiophenes: [7]Helicene and Double Helicene, a D2-Symmetric Dimer of 3,3′-Bis(dithieno[2,3-b:3′,2′-d]thiophene)

The efficient synthesis of (TMS)2-[7]helicene (rac-3) and double helicene, a D2-symmetric dimer of 3,3′-bis(dithieno[2,3-b:3′,2′-d]thiophene) (rac-4) was developed. The crystal structures of 3 and 4 show both strong intermolecular π-π interactions and S···S interactions. UV/vis spectra reveal that b...

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Veröffentlicht in:Journal of organic chemistry 2009-01, Vol.74 (1), p.408-411
Hauptverfasser: Li, Chunli, Shi, Jianwu, Xu, Li, Wang, Yangguang, Cheng, Yanxiang, Wang, Hua
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Crystallography, X-Ray
Dimerization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Models, Molecular
Molecular Structure
Organic chemistry
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Preparations and properties
Stereoisomerism
Thiophenes - chemical synthesis
Thiophenes - chemistry
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Zusammenfassung:The efficient synthesis of (TMS)2-[7]helicene (rac-3) and double helicene, a D2-symmetric dimer of 3,3′-bis(dithieno[2,3-b:3′,2′-d]thiophene) (rac-4) was developed. The crystal structures of 3 and 4 show both strong intermolecular π-π interactions and S···S interactions. UV/vis spectra reveal that both 3 and 4 show significant π-electron delocalization.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802080g