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

Chuan-Zeng Wang; Rie Kihara; Xing Feng; Pierre Thuéry; Carl Redshaw; Takehiko Yamato

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 University of Hull [United Kingdom]

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.

Document type :

Journal articles

Domain :

Chemical Sciences / Material chemistry

Complete list of metadatas

https://hal-cea.archives-ouvertes.fr/cea-01459698
Contributor : Serge Palacin <>
Submitted on : Tuesday, February 7, 2017 - 1:54:37 PM
Last modification on : Saturday, February 9, 2019 - 6:24:02 PM

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

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

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