Pyrene-based color-tunable dipolar molecules: Synthesis, characterization and optical properties

Wang, Chuan Zeng; Feng, Xing; Kowser, Zannatul; Wu, Chong; Akther, Thamina; Elsegood, Mark R J; Redshaw, Carl; Yamato, Takehiko

Abstract

© 2018 Elsevier Ltd A controllable regioselective approach to achieve dipolar functionalization at the active sites (1,3-positions) and K-region (5,9-positions) of pyrene is demonstrated. Following this strategy, a set of dipolar 1,3-diphenyl-5,9-di(4-R-phenylethynyl)pyrenes were synthesized and systematically investigated by 1 H/ 13 C NMR spectroscopy, X-ray crystallography, electronic spectra, as well as by theoretical calculations. By adjusting the substituents at the 5,9-positions of pyrene, the pyrene-based dipolar molecules 4 (H, F, OMe, CN, CHO, NMe 2 ) exhibit tunable optical properties with a wide emission band from blue (437 nm) to orange-red (571 nm).

Citation

Wang, C. Z., Feng, X., Kowser, Z., Wu, C., Akther, T., Elsegood, M. R. J., Redshaw, C., & Yamato, T. (2018). Pyrene-based color-tunable dipolar molecules: Synthesis, characterization and optical properties. Dyes and pigments : an international journal, 153, 125-131. https://doi.org/10.1016/j.dyepig.2018.01.003

• Journal Article Type: Article
• Acceptance Date: Jan 4, 2018
• Online Publication Date: Jan 6, 2018
• Publication Date: Jun 1, 2018
• Deposit Date: Mar 4, 2018
• Publicly Available Date: Jan 7, 2019
• Print ISSN: 0143-7208
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 153
• Pages: 125-131
• DOI: https://doi.org/10.1016/j.dyepig.2018.01.003
• Keywords: regioselective synthesis; pyrene chemistry; K-region; tunable emission; dipolar molecules Corresponding Author Takehiko Yamato Corresponding Author's Institution
• Public URL: https://hull-repository.worktribe.com/output/710257
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0143720817324324?via%3Dihub
• Additional Information: This article is maintained by: Elsevier; Article Title: Pyrene-based color-tunable dipolar molecules: Synthesis, characterization and optical properties; Journal Title: Dyes and Pigments; CrossRef DOI link to publisher maintained version: http://dx.doi.org/10.1016/j.dyepig.2018.01.003; Content Type: article; Copyright: © 2018 Elsevier Ltd. All rights reserved.
• Contract Date: Mar 5, 2018