Interactions-stabilized metastable trans-isomers and force-induced ESIPT release

Yiming Li; Zefeng Han; Hao Gu; Yuanbo Wang; Sheng Lu; Fang Wang; Xiaoqiang Chen

doi:10.1016/j.dyepig.2024.112560

Interactions-stabilized metastable trans-isomers and force-induced ESIPT release

Yiming Li, Zefeng Han, Hao Gu, Yuanbo Wang, Sheng Lu, Fang Wang, Xiaoqiang Chen

COLLEGE OF CHEMICAL ENGINEERING

Nanjing Tech University

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

Cis/trans isomerization is a candidate for immense fields, especially metastable states offering distinctive properties that arouse wide interests, but their stabilization remains challenging. We report a novel strategy to stabilize the thermodynamically metastable trans-isomers of 2-(2′-hydroxyphenyl)-4,5-diphenylimidazole (HDPI) derivatives, by introducing multiple intermolecular interactions. The TPE-HDPI compound with tetraphenylethylene (TPE) moiety promoted abundant intermolecular interactions to form trans-isomers in crystals, as confirmed by crystal and Hirschfeld surface analysis. The grinding-induced ESIPT release phenomenon observed by TRES spectra provides evidence for the transformation from the trans- to the cis- configuration.

Original language	English
Article number	112560
Journal	Dyes and Pigments
Volume	235
DOIs	https://doi.org/10.1016/j.dyepig.2024.112560
State	Published - Apr 2025

Keywords

Cis and trans states
Excited-state intermolecular proton transfer (ESIPT)
Intermolecular interactions
Isomerization

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10.1016/j.dyepig.2024.112560

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title = "Interactions-stabilized metastable trans-isomers and force-induced ESIPT release",

abstract = "Cis/trans isomerization is a candidate for immense fields, especially metastable states offering distinctive properties that arouse wide interests, but their stabilization remains challenging. We report a novel strategy to stabilize the thermodynamically metastable trans-isomers of 2-(2′-hydroxyphenyl)-4,5-diphenylimidazole (HDPI) derivatives, by introducing multiple intermolecular interactions. The TPE-HDPI compound with tetraphenylethylene (TPE) moiety promoted abundant intermolecular interactions to form trans-isomers in crystals, as confirmed by crystal and Hirschfeld surface analysis. The grinding-induced ESIPT release phenomenon observed by TRES spectra provides evidence for the transformation from the trans- to the cis- configuration.",

keywords = "Cis and trans states, Excited-state intermolecular proton transfer (ESIPT), Intermolecular interactions, Isomerization",

author = "Yiming Li and Zefeng Han and Hao Gu and Yuanbo Wang and Sheng Lu and Fang Wang and Xiaoqiang Chen",

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doi = "10.1016/j.dyepig.2024.112560",

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T1 - Interactions-stabilized metastable trans-isomers and force-induced ESIPT release

AU - Li, Yiming

AU - Han, Zefeng

AU - Gu, Hao

AU - Wang, Yuanbo

AU - Lu, Sheng

AU - Wang, Fang

AU - Chen, Xiaoqiang

PY - 2025/4

Y1 - 2025/4

N2 - Cis/trans isomerization is a candidate for immense fields, especially metastable states offering distinctive properties that arouse wide interests, but their stabilization remains challenging. We report a novel strategy to stabilize the thermodynamically metastable trans-isomers of 2-(2′-hydroxyphenyl)-4,5-diphenylimidazole (HDPI) derivatives, by introducing multiple intermolecular interactions. The TPE-HDPI compound with tetraphenylethylene (TPE) moiety promoted abundant intermolecular interactions to form trans-isomers in crystals, as confirmed by crystal and Hirschfeld surface analysis. The grinding-induced ESIPT release phenomenon observed by TRES spectra provides evidence for the transformation from the trans- to the cis- configuration.

AB - Cis/trans isomerization is a candidate for immense fields, especially metastable states offering distinctive properties that arouse wide interests, but their stabilization remains challenging. We report a novel strategy to stabilize the thermodynamically metastable trans-isomers of 2-(2′-hydroxyphenyl)-4,5-diphenylimidazole (HDPI) derivatives, by introducing multiple intermolecular interactions. The TPE-HDPI compound with tetraphenylethylene (TPE) moiety promoted abundant intermolecular interactions to form trans-isomers in crystals, as confirmed by crystal and Hirschfeld surface analysis. The grinding-induced ESIPT release phenomenon observed by TRES spectra provides evidence for the transformation from the trans- to the cis- configuration.

KW - Cis and trans states

KW - Excited-state intermolecular proton transfer (ESIPT)

KW - Intermolecular interactions

KW - Isomerization

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DO - 10.1016/j.dyepig.2024.112560

M3 - 文章

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SN - 0143-7208

VL - 235

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 112560

ER -

Interactions-stabilized metastable trans-isomers and force-induced ESIPT release

Abstract

Keywords

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