Pierre Thuéry
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
Chuan-Zeng Wang
Rie Kihara
Xing Feng
Pierre Thuery
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 |
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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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