Sulfur-annulated hexa-peri-hexabenzocoronene decorated with phenylthio groups at the periphery

Tan YZ, Osella S, Liu Y, Yang B, Beljonne D, Feng X, Muellen K (2015)

Publication Type: Journal article

Publication year: 2015

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 54

Pages Range: 2927-2931

Journal Issue: 10

DOI: 10.1002/anie.201409932

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.

Involved external institutions

Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research DE Germany (DE) University of Mons / Université de Mons BE Belgium (BE)

How to cite

APA:

Tan, Y.-Z., Osella, S., Liu, Y., Yang, B., Beljonne, D., Feng, X., & Muellen, K. (2015). Sulfur-annulated hexa-peri-hexabenzocoronene decorated with phenylthio groups at the periphery. Angewandte Chemie International Edition, 54(10), 2927-2931. https://doi.org/10.1002/anie.201409932

MLA:

Tan, Yuan-Zhi, et al. "Sulfur-annulated hexa-peri-hexabenzocoronene decorated with phenylthio groups at the periphery." Angewandte Chemie International Edition 54.10 (2015): 2927-2931.

BibTeX: Download