Short axially asymmetrically 1,3-disubstituted pyrene-based color-tunable emitters: Synthesis, characterization and optical properties

Wang, Chuan Zeng; Pang, Zi Jin; Yu, Ze Dong; Zeng, Zhao Xuan; Zhao, Wen Xuan; Zhou, Zi Yan; Redshaw, Carl; Yamato, Takehiko

Abstract

In contrast to conventional pyrene-based emitters which feature D-π-A type structures, a new class of emitters possessing a short axis are gaining interest owing to both their academic importance and promising applications in organic optoelectronic materials. Herein, donor and acceptor substituents were introduced at 1-, 3-positions by employing a two step bromination reaction. Two 1-donor-3-acceptor pyrenes were systematically investigated by 1H/13C NMR spectroscopy, optical spectroscopy, and theoretical calculations. The preliminary research of the substituent positions and substitutions pattern on the properties of the materials as well as on the frontier orbitals is reported. The experimental results indicated the strong impact on the photophysical properties endowed with the possibility of precise color-control of pyrene derivatives through substituent variation.

Citation

Wang, C. Z., Pang, Z. J., Yu, Z. D., Zeng, Z. X., Zhao, W. X., Zhou, Z. Y., Redshaw, C., & Yamato, T. (2021). Short axially asymmetrically 1,3-disubstituted pyrene-based color-tunable emitters: Synthesis, characterization and optical properties. Tetrahedron, 78, Article 131828. https://doi.org/10.1016/j.tet.2020.131828

• Journal Article Type: Article
• Acceptance Date: Nov 28, 2020
• Online Publication Date: Dec 3, 2020
• Publication Date: Jan 8, 2021
• Deposit Date: Dec 4, 2020
• Publicly Available Date: Dec 4, 2021
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 78
• Article Number: 131828
• DOI: https://doi.org/10.1016/j.tet.2020.131828
• Keywords: Pyrene chemistry; Asymmetric synthesis; Color-tunable emitters; Photo-physical properties; Density Functional Theory
• Public URL: https://hull-repository.worktribe.com/output/3670791
• Publisher URL: https://www.sciencedirect.com/science/article/abs/pii/S0040402020310760?via%3Dihub