Coumarin–tetraphenylethylene regioisomers: synthesis, photophysical and aggregation-induced emission properties

Reddy, T. Sheshashena; Moon, Hyungkyu; Choi, Myung–Seok

doi:10.1039/d0nj00037j

Cited by 4 publications

(2 citation statements)

References 46 publications

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“…Naphthalimide-based TPE (5) is highly emissive and mechanochromic in solid state. [4] Coumarin-based TPE regioisomers (6) reported by Myung-Seok Choi and his colleagues [5] showed strong fluorescent intensity and AIE enhancement. Notably, C7 substituted coumarin-TPE showed red-shift and large Stokes shift in its absorption spectrum.…”

Section: Introductionmentioning

confidence: 95%

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Synthesis of 1,1’‐diphenyl‐2‐thienyl‐2’‐(4‐substituted‐styryl)ethenes via oxidative Heck coupling reaction and photophysical studies

Thanh

Hai

Nguyễn

et al. 2021

Vietnam Journal of Chemistry

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In this paper, we report the synthesis of four new 1,1’‐diphenyl‐2‐thienyl‐2’‐(4‐substituted‐styryl) ethenes via one‐step oxidative Heck coupling reaction of 1,1’‐diphenyl‐2,2’‐dithienylethene (DPDTE). This is a useful method to alkenylate DPDTE in order to enhance its fluorescence as well as its aggregation‐induced emission (AIE) properties. 1,1’‐Diphenyl‐2‐thienyl‐2’‐(4‐methylstyryl)ethene showed low fluorescent intensity in CHCl3 solution but very high AIE intensities. On the other hand, 1,1’‐diphenyl‐2‐thienyl‐2’‐(4‐acetoxystyryl)ethene showed both high fluorescence in CHCl3 solution and AIE intensities.

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Section: Introductionmentioning

confidence: 95%

“…In one method, the first step is the bromination of TPE by N-bromosuccinimide, followed by the synthesis of phosphonium salt. [4,5] The final step is a Wittig olefination. In another method, a vinyl moiety was first introduced into TPE for further Heck crosscoupling reactions with aryl bromides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,1’‐diphenyl‐2‐thienyl‐2’‐(4‐substituted‐styryl)ethenes via oxidative Heck coupling reaction and photophysical studies

Thanh

Hai

Nguyễn

et al. 2021

Vietnam Journal of Chemistry

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A Novel Approach to the Structural Design of Dual‐State Emission Luminogens by Combining Tetraphenylethylene with Anthracene via Dihydroisoxazole

Lu,

Zhao,

Sun

2024

ChemPhotoChem

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Dual‐state emission luminescent materials (DSEgens), which exhibit bright emissions in boththe solid state and solution, have been attracting research interest in the design of multifunctional materials.The delicate manipulation of molecular structures remains challenging in the synthesis of DSEgens. In this article, two novel molecules with dual‐state emission were synthesized by combining tetraphenylethylene with anthracene via dihydroisoxazole. Tetraphenylethylene acts as a solid‐state emitter, while the anthracene core functions as an emitter in the solution state to achieve DSE fluorescence properties. The THF/DCM mixture resulted in successfully obtaining the crystal structures of TPE−An−H and TPE−An−Cl. The quantum yields (QYs) of TPE−An−H were 31 % and 42 % in EA and the solid state, respectively, while TPE−An−Cl exhibited QYs of 32 % and 34 %. The novel synthesis method in this paper combines AIE with ACQ via dihydroisoxazole to achieve dual‐state emission, offering a new and concise approach.

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A simple and sensitive coumarin-based fluorescence probe (ZXD-1) for determination of hydrogen peroxide and its application in bioimaging

Zeng,

Yu,

Liu

et al. 2024

Journal of Molecular Structure

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Coumarin–tetraphenylethylene regioisomers: synthesis, photophysical and aggregation-induced emission properties

Abstract: Coumarin–tetraphenylethylene (CTPE) regioisomers with different linkage types and substitution positions (coumarin C5, C6, C7) were synthesized, characterized, photophysical and aggregation-induced emission properties reported.

Cited by 4 publications

References 46 publications

Synthesis of 1,1’‐diphenyl‐2‐thienyl‐2’‐(4‐substituted‐styryl)ethenes via oxidative Heck coupling reaction and photophysical studies

Synthesis of 1,1’‐diphenyl‐2‐thienyl‐2’‐(4‐substituted‐styryl)ethenes via oxidative Heck coupling reaction and photophysical studies

A Novel Approach to the Structural Design of Dual‐State Emission Luminogens by Combining Tetraphenylethylene with Anthracene via Dihydroisoxazole

A simple and sensitive coumarin-based fluorescence probe (ZXD-1) for determination of hydrogen peroxide and its application in bioimaging

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