Substituent effects on the mechanochromic behaviour of pyrene-based AIEgens

Yang, Guang; Xue, Zeng Min; Liang, Ling; Meng, Fei; Liu, Kai Yue; Wang, Jia Hao; Lin, Hong Tao; Zhao, Wen Xuan; Chen, Shu Hai; Yamato, Takehiko; Redshaw, Carl; Wang, Chuan Zeng

Abstract

It is extremely significant and desirable to integrate the fascinating properties of mechanochromism and aggregation-induced emission (AIE) in one simple molecule. Herein, pyrene-based aggregation-induced emission luminogens (AIEgens) with mechanofluorochromic (MFC) properties solve the traditionally existing aggregation-caused quenching (ACQ) challenge. Three cyanoethylene-functionalized pyrene-based derivatives were designed and synthesized. All compounds exhibit remarkable aggregation-enhanced emission (AEE) activity by a 3–20 times enhancement in mixed H2O/THF solutions. More importantly, high fluorescence efficiency was recorded in the solid state, especially for the luminogen 2c, with more than 200 times observed increased efficiency from 0.3% in solution to 69.8% in the solid state. Meanwhile, excellent mechanochromism properties and reversibility against the grinding treatment was systematically investigated. The excellent fatigue resistance properties are a necessity for potential applications in the field of anti-counterfeiting fluorescent inks and for the encryption of security information.

Citation

Yang, G., Xue, Z. M., Liang, L., Meng, F., Liu, K. Y., Wang, J. H., Lin, H. T., Zhao, W. X., Chen, S. H., Yamato, T., Redshaw, C., & Wang, C. Z. (2025). Substituent effects on the mechanochromic behaviour of pyrene-based AIEgens. Journal of Photochemistry and Photobiology A: Chemistry, 459, 116020. https://doi.org/10.1016/j.jphotochem.2024.116020

• Journal Article Type: Article
• Acceptance Date: Sep 7, 2024
• Online Publication Date: Sep 16, 2024
• Publication Date: Feb 1, 2025
• Deposit Date: Sep 18, 2024
• Publicly Available Date: Sep 17, 2026
• Journal: Journal of Photochemistry and Photobiology A: Chemistry
• Print ISSN: 1010-6030
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 459
• Pages: 116020
• DOI: https://doi.org/10.1016/j.jphotochem.2024.116020
• Public URL: https://hull-repository.worktribe.com/output/4832878
• Additional Information: This article is maintained by: Elsevier; Article Title: Substituent effects on the mechanochromic behaviour of pyrene-based AIEgens; Journal Title: Journal of Photochemistry and Photobiology A: Chemistry; CrossRef DOI link to publisher maintained version: https://doi.org/10.1016/j.jphotochem.2024.116020; Content Type: article; Copyright: © 2024 Elsevier B.V. All rights are reserved, including those for text and data mining, AI training, and similar technologies.