Synthesis, Structure and Photophysical Properties of Pyrene-based [5]Helicenes: an Experimental and Theoretical Study

Chuan-Zeng Wang 1 Rie Kihara 1 Xing Feng 1, 2 Pierre Thuéry 3 Carl Redshaw 4 Takehiko Yamato 1
1 Saga University [Japon]
2 School of Printing and Packaging Engineering
3 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
4 Hull University
Abstract : Pyrene-cored [5]helicenes were prepared by a facile, efficient Wittig reaction and an intramolecular photocyclization reaction utilising 2,7-di-tert-butylpyrene-4-carbaldehyde and naphthalene/pyrene-based phosphorus ylides. Optical properties based on UV À vis absorption and fluorescence spectra were investigated. X-ray crystallography revealed that the pyrene-based [5]helicenes exhibited strong face-to-face p À p interactions and edge-to-face p À p interactions. HOMO and LUMO energies and molecular orbitals were also studied by density functional theory (DFT) calculations. This study has revealed that the torsion angle of the helical structure plays a role in determining the p À p interactions and the frontier molecular orbital energy levels. Thus, pyrene-based helicenes need to be considered when one designs new highly efficient organic light-emitting diodes and organic semiconductor materials.
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https://hal-cea.archives-ouvertes.fr/cea-01459698
Contributeur : Serge Palacin <>
Soumis le : mardi 7 février 2017 - 13:54:37
Dernière modification le : mardi 6 novembre 2018 - 14:00:17

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Chuan-Zeng Wang, Rie Kihara, Xing Feng, Pierre Thuéry, Carl Redshaw, et al.. Synthesis, Structure and Photophysical Properties of Pyrene-based [5]Helicenes: an Experimental and Theoretical Study. ChemistrySelect, Wiley, 2017, 2, pp.1436 - 1441. 〈http://onlinelibrary.wiley.com/doi/10.1002/slct.201601327/full〉. 〈10.1002/slct.201601327〉. 〈cea-01459698〉

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