Development and application of Diels-Alder adducts displaying AIE properties

Timothy L. Gialelis; Tze Cin Owyong; Siyang Ding; Wenyi Li; Maoxing Yu; Neil M. O’Brien-Simpson; Zujin Zhao; Jonathan M. White; Bicheng Yao; Yuning Hong

Cell Reports Physical Science (Feb 2022)

Development and application of Diels-Alder adducts displaying AIE properties

Timothy L. Gialelis,
Tze Cin Owyong,
Siyang Ding,
Wenyi Li,
Maoxing Yu,
Neil M. O’Brien-Simpson,
Zujin Zhao,
Jonathan M. White,
Bicheng Yao,
Yuning Hong

Affiliations

Timothy L. Gialelis: Department of Biochemistry and Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Tze Cin Owyong: Department of Biochemistry and Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia; School of Chemistry, Bio21 Institute, The University of Melbourne, Parkville, VIC 3010, Australia
Siyang Ding: Department of Biochemistry and Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Wenyi Li: Melbourne Dental School, Bio21 Institute, The University of Melbourne, Parkville, VIC 3010, Australia
Maoxing Yu: State Key Laboratory of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, South China University of Technology, 510640 Guangzhou, China
Neil M. O’Brien-Simpson: Melbourne Dental School, Bio21 Institute, The University of Melbourne, Parkville, VIC 3010, Australia
Zujin Zhao: State Key Laboratory of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, South China University of Technology, 510640 Guangzhou, China
Jonathan M. White: School of Chemistry, Bio21 Institute, The University of Melbourne, Parkville, VIC 3010, Australia
Bicheng Yao: Department of Biochemistry and Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia
Yuning Hong: Department of Biochemistry and Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia; Corresponding author

Journal volume & issue: Vol. 3, no. 2
p. 100766

Abstract

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Summary: Exploring organic reactions to construct novel molecules with aggregation-induced emission (AIE) features is an essential branch of AIE research. The fast-paced application of AIE materials in various disciplines, including photoelectricity, molecular biology, medicine, and materials science, has led to an ever-growing need for new AIE molecules. Unlike the synthesis of most “earlier generations” of AIE fluorogens (AIEgens) that require tedious and harsh reactions, chemists now shift their synthetic focus to a selection of reliable and straightforward reactions. The Diels-Alder reaction has been overlooked in this field. Herein, we report a catalyst-free Diels-Alder reaction between 1,3-diphenylisobenzofuran and a series of electron-deficient alkynes to create AIEgens. Photophysical properties of our synthesized 1,3,4-triphenyl-1,4-dihydro-1,4-epoxynaphthalene (ENAP) derivatives are studied systematically, manifesting their AIE characteristics and structure-fluorescence property relationships. Finally, we highlight the diverse applications of some selected ENAP derivatives in latent fingerprint detection, cell imaging, and bacterial staining.

Published in Cell Reports Physical Science

ISSN: 2666-3864 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Science: Physics
Website: https://www.cell.com/cell-reports-physical-science

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