Intermolecular Hydrogen-Bond-Assisted Solid-State Dual-Emission Molecules with Mechanical Force-Induced Enhanced Emission

Wang, Xiaohui; Zhang, Jianyu; Mao, Xiaoyu; Liu, Yiwei; Li, Ruikuan; Bai, Jie; Zhang, Jun; Redshaw, Carl; Feng, Xing; Tang, Ben Zhong

Abstract

Hydrogen bonds not only play a crucial role in the life sciences but also endow molecules with fantastic physical and chemical properties, which help in the realization of their high-tech applications. This work presents an efficient strategy for achieving highly efficient solid-state dual-emission blue emitters with mechanical force-induced enhanced emission properties via intermolecular hydrogen bonds via novel pyrene-based intermediates, namely, 1,3,6,8-tetrabromo-2,7-dihydroxypyrene (1) and 1,3,6,8-tetrabromo-2-hydroxypyrene (2), prepared via hydroxylation and bromination of pyrene in high yields. Moreover, further use of a classical Pd-catalyzed coupling reaction affords new pyrene-based luminescent materials 3-5, which display high thermal stability (in range of 336-447 °C), blue emission (<463 nm), and high quantum yields in solution. Interestingly, with the monosubstituted hydroxyl (OH) or methoxy (OMe) group located at position 2 of pyrene, compounds 4a and 5 display exciting dual emission with mechanical force-induced enhanced emission properties, due to the presence of several hydrogen-bond interactions. Moreover, this series of compounds exhibits numerous advantages, for example, deeper blue emission with a narrower full width at half-maximum, a stronger steric effect, and higher hydrophilicity. Thus, these novel bromopyrene intermediates and related pyrene-based luminescent materials will pave the way for further exploration of novel organic solid-state luminescent materials for potential application in organic electronics, bioimaging, chemosensors, etc.

Citation

Wang, X., Zhang, J., Mao, X., Liu, Y., Li, R., Bai, J., Zhang, J., Redshaw, C., Feng, X., & Tang, B. Z. (2022). Intermolecular Hydrogen-Bond-Assisted Solid-State Dual-Emission Molecules with Mechanical Force-Induced Enhanced Emission. Journal of Organic Chemistry, 87(13), 8503–8514. https://doi.org/10.1021/acs.joc.2c00617

• Journal Article Type: Article
• Acceptance Date: Jun 8, 2022
• Online Publication Date: Jun 21, 2022
• Publication Date: Jul 1, 2022
• Deposit Date: Sep 6, 2022
• Publicly Available Date: Jun 22, 2023
• Journal: Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 87
• Issue: 13
• Pages: 8503–8514
• DOI: https://doi.org/10.1021/acs.joc.2c00617
• Keywords: Aromatic compounds; Crystals; Hydrocarbons; Mixtures; Molecular interactions
• Public URL: https://hull-repository.worktribe.com/output/4041350