Non-doped, solid-state red-emitting phenothiazine-pyrene chalcones: Synthesis, aggregation-induced emission enhancement and mechanofluorochromism

被引：0

作者：

Kumari, Reshma ^{[1
]}

Milton, Marilyn Daisy ^{[1
]}

机构：

[1] Functional Organic Molecules Synthesis Laboratory, Department of Chemistry, University of Delhi, Delhi

来源：

Journal of Photochemistry and Photobiology A: Chemistry | 2025年 / 462卷

关键词：

Aggregation-induced emission enhancement (AIEE); Anti-counterfeiting; Mechaofluorochromism (MFC); Organic red-emitting dyes; Pyrene; Solid-state emission;

D O I：

10.1016/j.jphotochem.2024.116222

中图分类号：

学科分类号：

摘要：

We report the synthesis of a new series of red-emitting phenothiazine chalcones bearing pyrene moiety with the objective of improving the emission characteristics in the solid-state. The compounds exhibited large Stokes shift, positive solvatochromism, aggregation-induced emission enhancement, and reversible mechanofluorochromism (MFC). In contrast to the typical quenching observed in π–π stacked organic compounds, the pyrene-chalcone, Ch-H, which showed intermolecular π–π stacking through single crystal XRD studies, displayed a high quantum yield of 94.3% in solid-state, which was attributed to the crystallization-induced emission enhancement (CIEE) phenomenon. Interestingly, another pyrene-chalcone, Ch-Np, which lacked π–π stacking as observed through single crystal XRD, exhibited a poor quantum yield of 7.17% in the solid-state. The molar extinction coefficients of the solution of compounds were higher than the well-known N719 dye. The potential of highly luminescent chalcone, Ch-H, in anti-counterfeiting applications, was further demonstrated by writing and stamping on black paper, visible only under 365 nm but not under ordinary daylight. © 2024 Elsevier B.V.

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