Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 10, Pages 2927-2931Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409932
Keywords
annulation; nanographene; functionalization; sulfur; thiolation
Categories
Funding
- ERC
- DFG [SPP 1459]
- EU Project GENIUS
- MoQuas
- UPGRADE
- Graphene Flagship [CNECT-ICT-604391]
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The chemical nature of the edge periphery essentially determines the physical properties of graphene. As a molecular-level model system, large polycyclic aromatic hydrocarbons, that is, so-called nanographenes, can be chemically modified through either edge functionalization or doping with heteroatoms. Although the synthetic methods for edge substitution are well-developed, incorporation with heteroatoms by the bay annulation of large PAHs remains an enormous challenge. In this study, we present a feasible peripheral sulfur annulation of hexa-peri-hexabenzocoronene (HBC) by thiolation of perchlorinated HBC. The tri-sulfur-annulated HBC and di-sulfur-annulated HBC decorated with phenylthio groups were obtained and characterized by X-ray diffraction, revealing their distinct sulfur-annulated peripheral structure. Associated with theoretical calculations, we propose that the regioselective sulfur annulation results from the minimization of strain in the aromatic backbone. We further demonstrate the structure-correlated property modulation by sulfur annulation, manifested by a decrease in band gap and tunable redox activity.
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