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Synthesis and physical properties of [4]cyclo-3,7-dibenzo[b,d]thiophene and its S,S-dioxide

Synthesis and physical properties of [4]cyclo-3,7-dibenzo[b,d]thiophene and its S,S-dioxide

Authors :
Eiichi Kayahara
Xue Zhai
Shigeru Yamago
Source :
Canadian Journal of Chemistry. 95:351-356
Publication Year :
2017
Publisher :
Canadian Science Publishing, 2017.

Abstract

Cyclic tetramers of 3,7-dibenzo[b,d]thiophene (DBT) and 3,7-dibenzo[b,d]thiophene-5,5-dioxide (DBTO), i.e., [4]cyclo-DBT ([4]CDBT) and [4]cyclo-DBTO ([4]CDBTO), respectively, are synthesized by the platinum-mediated assembly of bis-metallated DBT and DBTO and the subsequent reductive elimination of platinum. This is the first example of the synthesis of sulfur-containing cycloparaphenylene (CPP) derivatives. The structure of [4]CDBTO is unambiguously determined by the single crystal X-ray analysis. Theoretical and experimental analyses of their physical properties reveal the effect of the sulfur atom and sulfonyl group at the periphery of biphenyl units of the CPP.

Details

ISSN :
14803291 and 00084042
Volume :
95
Database :
OpenAIRE
Journal :
Canadian Journal of Chemistry
Accession number :
edsair.doi...........f8f44a285068c17e80fb7a46d8bdb4e4
Full Text :
https://doi.org/10.1139/cjc-2016-0474