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- Title
Sulfur-Annulated Hexa- peri-hexabenzocoronene Decorated with Phenylthio Groups at the Periphery.
- Authors
Tan, Yuan-Zhi; Osella, Silvio; Liu, Yi; Yang, Bo; Beljonne, David; Feng, Xinliang; Müllen, Klaus
- Abstract
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.
- Subjects
HEXABENZOCORONENES; SULFUR; ANNULATION; GRAPHENE; POLYCYCLIC aromatic hydrocarbons; X-ray diffraction
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 10, p2970
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201409932