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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… Click to show full 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.
Journal Title: Canadian Journal of Chemistry
Year Published: 2017
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