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Synthesis, structure and photophysical properties of pyrene–based [5]helicenes : an experimental and theoretical study

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

Authors

Pierre Thuéry

Chuan-Zeng Wang

Rie Kihara

Xing Feng

Pierre Thuery

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Takehiko Yamato



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−vis absorption and fluorescence spectra were investigated. X-ray crystallography revealed that the pyrene-based [5]helicenes exhibited strong face-to-face π−π interactions and edge-to-face π−π 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 π−π 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.

Citation

Thuéry, P., Wang, C., Kihara, R., Feng, X., Thuery, P., Redshaw, C., & Yamato, T. (2017). Synthesis, structure and photophysical properties of pyrene–based [5]helicenes : an experimental and theoretical study. ChemistrySelect, 2(4), 1436-1441. https://doi.org/10.1002/slct.201601327

Acceptance Date Jan 23, 2017
Online Publication Date Feb 3, 2017
Publication Date Feb 1, 2017
Deposit Date May 1, 2017
Publicly Available Date Mar 29, 2024
Journal ChemistrySelect
Electronic ISSN 2365-6549
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2
Issue 4
Pages 1436-1441
DOI https://doi.org/10.1002/slct.201601327
Keywords Pyrene-cored [5]helicenes; Photocyclization; π−π interactions; DFT calculations; Optical properties
Public URL https://hull-repository.worktribe.com/output/451212
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/slct.201601327/abstract
Additional Information Authors' accepted manuscript of article published in: ChemistrySelect, 2017, v.2, issue 4.

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