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New pyrrolo[3,2-b]pyrroles with AIE characteristics for detection of dichloromethane and chloroform

Yu, Shuning; Li, Shaoling; Xie, Zhixin; Liu, Wei; Islam, Md Monarul; Redshaw, Carl; Cao, Mei Juan; Chen, Qing; Feng, Xing

Authors

Shuning Yu

Shaoling Li

Zhixin Xie

Wei Liu

Md Monarul Islam

Mei Juan Cao

Qing Chen

Xing Feng



Abstract

Three new pyrrolo[3,2-b]pyrrole derivatives containing methoxyphenyl, pyrene or tetraphenylethylene (TPE) units (compounds 1–3) have been designed, synthesized and fully characterized. The aggregation-induced emission (AIE) properties of compounds 1–3 were tested in different water fraction (fw) of tetrahydrofuran (THF). The pyrrolo[3,2-b]pyrrole derivative 3 containing TPE units exhibited typical AIE features with an enhanced emission (∼32-fold) in the solid state versus in solution; compounds 1 and 2 exhibited an aggregation-caused quenching effect. In addition, the steric and electronic effects of the peripheral moieties on the emission behavior, both in solution and in the solid state, have been investigated. Moreover, pyrrolo[3,2-b]pyrrole 1 exhibits high sensitivity and selectivity for dichloromethane and chloroform solvents, with the system displaying a new emission peak and fast response time under ultraviolet irradiation.

Citation

Yu, S., Li, S., Xie, Z., Liu, W., Islam, M. M., Redshaw, C., Cao, M. J., Chen, Q., & Feng, X. (in press). New pyrrolo[3,2-b]pyrroles with AIE characteristics for detection of dichloromethane and chloroform. Luminescence, https://doi.org/10.1002/bio.4640

Journal Article Type Article
Acceptance Date Nov 7, 2023
Online Publication Date Dec 5, 2023
Deposit Date Dec 8, 2023
Publicly Available Date Dec 6, 2024
Journal Luminescence
Print ISSN 1522-7235
Electronic ISSN 1522-7243
Publisher Wiley
Peer Reviewed Peer Reviewed
DOI https://doi.org/10.1002/bio.4640
Keywords Aggregation-induced emission (AIE); Dichloromethane and chloroform molecules detection; Pyrrolo[3,2-b] pyrroles; Structure–property relationship
Public URL https://hull-repository.worktribe.com/output/4469983

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Copyright Statement
This is the peer reviewed version of the following article: Yu, S., Li, S., Xie, Z., Liu, W., Islam, M. M., Redshaw, C., Cao, M. J., Chen, Q., Feng, X., Luminescence 2023, 1., which has been published in final form at https://doi.org/10.1002/bio.4640. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.





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