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

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.-Z., 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: Feb 6, 2018
• 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.
• Contract Date: Feb 6, 2018