Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 29, Pages 9021-9024Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b04092
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Funding
- Alexander von Humboldt Foundation
- DFG [SPP 1459]
- Graphene Flagship [CNECT-ICT-604391]
- European Union Project MoQuaS
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A tandem demethylation-aryl borylation strategy was developed to synthesize OBO-doped tetrabenzo[a,f,j,o]perylenes (namely bistetracenes) and tetrabenzo [bc,ef,kl,no] coronenes (namely peritetracenes). The OBO-doped bistetracene analogues exhibited excellent stability and strong fluorescence, in contrast to the unstable all-carbon bistetracene. Single-crystal X-ray analysis for OBO-doped bistetracene revealed a twisted double [5]helicene structure, indicating that this synthesis is applicable to new heterohelicenes. Importantly, cyclo-dehydrogenation of the bistetracene analogues successfully produced the unprecedented heteroatom-doped peritetracenes, which opened up a new avenue to periacene-type nanographenes with stable zigzag edges.
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