Multiple photoluminescence from pyrene-fused hexaarylbenzenes with aggregation-enhanced emission features

Venkatesan, Perumal; Yamato, Takehiko; Elsegood, Mark R.J.; Wang, Chuan-Zeng; Noda, Yuki; Wu, Chong; Feng, Xing; Venatesan, Perumal; Cong, Hang; Elsegood, Mark R. J.; Warwick, Thomas G.; Teat, Simon J.; Redshaw, Carl; Yamato, Prof Takehiko

Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Multiple photoluminescence, which included monomer emission, excimer emission, and charge-transfer emission processes, has been observed from new pyrene-fused hexaarylbenzene (HAB) compounds, which were synthesized in high yields through a Diels–Alder reaction between bis(2-tert-butylpyren-6-yl)acetylene and tetraphenylcyclopentadienone. Although the differentiation between the two molecules only arose from the geometrical position of one of the pyrenes, the NMR spectra, crystal packing, and physicochemical properties of these pyrene-based HAB hybrids were distinctly different in both the solution and aggregate states. X-ray diffraction analysis clearly indicated that the pyrene moieties adopted different crystal packing arrangements in the crystalline state that could induce a multiple-photoluminescence phenomenon.

Citation

Venkatesan, P., Yamato, T., Elsegood, M. R., Wang, C.-Z., Noda, Y., Wu, C., Feng, X., Venatesan, P., Cong, H., Elsegood, M. R. J., Warwick, T. G., Teat, S. J., Redshaw, C., & Yamato, P. T. (2018). Multiple photoluminescence from pyrene-fused hexaarylbenzenes with aggregation-enhanced emission features. Asian journal of organic chemistry an ACES journal, 7(2), 444-450. https://doi.org/10.1002/ajoc.201700563

• Journal Article Type: Article
• Acceptance Date: Dec 22, 2017
• Online Publication Date: Jan 15, 2018
• Publication Date: Jan 15, 2018
• Deposit Date: Mar 4, 2018
• Publicly Available Date: Jan 16, 2019
• Print ISSN: 2193-5807
• Publisher: Wiley-VCH Verlag
• Peer Reviewed: Peer Reviewed
• Volume: 7
• Issue: 2
• Pages: 444-450
• DOI: https://doi.org/10.1002/ajoc.201700563
• Keywords: Aggregation; Hexaarylbenzenes; Luminescence; Photochemistry; Pyrenes
• Public URL: https://hull-repository.worktribe.com/output/710219
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/ajoc.201700563/abstract
• Additional Information: The peer-reviewed version of the following article: C.-Z. Wang, Y. Noda, C. Wu, X. Feng, P. Venkatesan, H. Cong, M. R. J. Elsegood, T. G. Warwick, S. J. Teat, C. Redshaw, T. Yamato, Asian J. Org. Chem. 2018, 7, 444., which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/ajoc.201700563. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving.
• Contract Date: Mar 6, 2018