We report a highly efficient synthetic methodology toward tri-N-annulated hexarylenes from easily available N-annulated perylenes, which is favored by the oxidative ring fusion driven by DDQ/Sc(OTf)3. To assist the characterization of the new compounds, quantum-chemical calculations of structural and spectroscopic properties have been carried out for three oligomers of N-annulated rylenes. It is shown that tri-N-annulated hexarylene dyes display remarkably large dipole moments likely associated with the formation of H aggregates, as suggested by the marked concentration dependence of the measured UV-vis spectra. It is suggested that the combination of π-π stacking interactions and dipole-dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.
Tri-N-annulated Hexarylene: an Approach to Well-defined Graphene Nanoribbons with large Dipoles / Y. Li; J. Gao; S. Di Motta; F. Negri; Z. Wang. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - ELETTRONICO. - 132:(2010), pp. 4208-4213. [10.1021/ja100276x]
Tri-N-annulated Hexarylene: an Approach to Well-defined Graphene Nanoribbons with large Dipoles
DI MOTTA, SIMONE;NEGRI, FABRIZIA;
2010
Abstract
We report a highly efficient synthetic methodology toward tri-N-annulated hexarylenes from easily available N-annulated perylenes, which is favored by the oxidative ring fusion driven by DDQ/Sc(OTf)3. To assist the characterization of the new compounds, quantum-chemical calculations of structural and spectroscopic properties have been carried out for three oligomers of N-annulated rylenes. It is shown that tri-N-annulated hexarylene dyes display remarkably large dipole moments likely associated with the formation of H aggregates, as suggested by the marked concentration dependence of the measured UV-vis spectra. It is suggested that the combination of π-π stacking interactions and dipole-dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.