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Tri-N-annulated hexarylene: an approach to well-defined graphene nanoribbons with large dipoles

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... Full description

Journal Title: Journal of the American Chemical Society 31 March 2010, Vol.132(12), pp.4208-13
Main Author: Li, Yan
Other Authors: Gao, Jing , Di Motta, Simone , Negri, Fabrizia , Wang, Zhaohui
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; PMID: 20218557 Version:1 ; DOI: 10.1021/ja100276x
Link: http://pubmed.gov/20218557
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recordid: medline20218557
title: Tri-N-annulated hexarylene: an approach to well-defined graphene nanoribbons with large dipoles
format: Article
creator:
  • Li, Yan
  • Gao, Jing
  • Di Motta, Simone
  • Negri, Fabrizia
  • Wang, Zhaohui
subjects:
  • Hexane -- Chemical Properties
  • Chemical Synthesis -- Analysis
  • Graphene -- Chemical Properties
ispartof: Journal of the American Chemical Society, 31 March 2010, Vol.132(12), pp.4208-13
description: 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 pi-pi stacking interactions and dipole-dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; PMID: 20218557 Version:1 ; DOI: 10.1021/ja100276x
fulltext: fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titleTri-N-annulated hexarylene: an approach to well-defined graphene nanoribbons with large dipoles
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descriptionWe 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 pi-pi stacking interactions and dipole-dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.
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descriptionWe 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 pi-pi stacking interactions and dipole-dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.
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abstractWe 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 pi-pi stacking interactions and dipole-dipole interactions may favor the formation of highly ordered supramolecular structures, resulting in enhanced charge carrier mobilities.
doi10.1021/ja100276x
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date2010-03-31