Construction of emissive azobenzene derivatives by hydroxylation and aggregation

Jiawei You; Shuai Zhang; Qiuying Li; Weijie Zhang; Huili Ma; Jianquan Hou; Engui Zhao; Zikai He

doi:10.1016/j.dyepig.2023.111662

Construction of emissive azobenzene derivatives by hydroxylation and aggregation

Jiawei You, Shuai Zhang, Qiuying Li, Weijie Zhang, Huili Ma, Jianquan Hou, Engui Zhao, Zikai He

SCHOOL OF FLEXIBLE ELECTRONICS(FUTURE TECHNOLOGIES)|INSTITUTE OF ADVANCED MATERIALS(IAM)

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

4 Scopus citations

Abstract

Azobenzene derivatives are well-known for their photoisomerization. Due to E-Z isomerization, azobenzene derivatives are seldom fluorescent, which hinders their high-tech applications. Herein, we report two azobenzene derivatives, TPE-Azo-OH and TPE-Azo-2OH, with photoisomerization properties and solid-state fluorescence. Theoretical investigations revealed that the unusual fluorescence contributed from the S₂ (π, π*) by state-mixing in solid state. TPE-Azo-2OH exhibits even stronger fluorescence due to the suppression of photoisomerization by intramolecular hydrogen bond. Furthermore, upon reduction, these azobenzene derivatives exhibit fluorescence transformation from red to green. These new azobenzene derivatives with AIE attributes and stimuli-responsiveness are expected to provide a new platform for developing photo-responsive luminescent materials.

Original language	English
Article number	111662
Journal	Dyes and Pigments
Volume	220
DOIs	https://doi.org/10.1016/j.dyepig.2023.111662
State	Published - Dec 2023

Keywords

Azobenzene
Fluorescence
Intramolecular hydrogen bond
Photoisomerization

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10.1016/j.dyepig.2023.111662

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title = "Construction of emissive azobenzene derivatives by hydroxylation and aggregation",

abstract = "Azobenzene derivatives are well-known for their photoisomerization. Due to E-Z isomerization, azobenzene derivatives are seldom fluorescent, which hinders their high-tech applications. Herein, we report two azobenzene derivatives, TPE-Azo-OH and TPE-Azo-2OH, with photoisomerization properties and solid-state fluorescence. Theoretical investigations revealed that the unusual fluorescence contributed from the S2 (π, π*) by state-mixing in solid state. TPE-Azo-2OH exhibits even stronger fluorescence due to the suppression of photoisomerization by intramolecular hydrogen bond. Furthermore, upon reduction, these azobenzene derivatives exhibit fluorescence transformation from red to green. These new azobenzene derivatives with AIE attributes and stimuli-responsiveness are expected to provide a new platform for developing photo-responsive luminescent materials.",

keywords = "Azobenzene, Fluorescence, Intramolecular hydrogen bond, Photoisomerization",

author = "Jiawei You and Shuai Zhang and Qiuying Li and Weijie Zhang and Huili Ma and Jianquan Hou and Engui Zhao and Zikai He",

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year = "2023",

month = dec,

doi = "10.1016/j.dyepig.2023.111662",

language = "英语",

volume = "220",

journal = "Dyes and Pigments",

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TY - JOUR

T1 - Construction of emissive azobenzene derivatives by hydroxylation and aggregation

AU - You, Jiawei

AU - Zhang, Shuai

AU - Li, Qiuying

AU - Zhang, Weijie

AU - Ma, Huili

AU - Hou, Jianquan

AU - Zhao, Engui

AU - He, Zikai

PY - 2023/12

Y1 - 2023/12

N2 - Azobenzene derivatives are well-known for their photoisomerization. Due to E-Z isomerization, azobenzene derivatives are seldom fluorescent, which hinders their high-tech applications. Herein, we report two azobenzene derivatives, TPE-Azo-OH and TPE-Azo-2OH, with photoisomerization properties and solid-state fluorescence. Theoretical investigations revealed that the unusual fluorescence contributed from the S2 (π, π*) by state-mixing in solid state. TPE-Azo-2OH exhibits even stronger fluorescence due to the suppression of photoisomerization by intramolecular hydrogen bond. Furthermore, upon reduction, these azobenzene derivatives exhibit fluorescence transformation from red to green. These new azobenzene derivatives with AIE attributes and stimuli-responsiveness are expected to provide a new platform for developing photo-responsive luminescent materials.

AB - Azobenzene derivatives are well-known for their photoisomerization. Due to E-Z isomerization, azobenzene derivatives are seldom fluorescent, which hinders their high-tech applications. Herein, we report two azobenzene derivatives, TPE-Azo-OH and TPE-Azo-2OH, with photoisomerization properties and solid-state fluorescence. Theoretical investigations revealed that the unusual fluorescence contributed from the S2 (π, π*) by state-mixing in solid state. TPE-Azo-2OH exhibits even stronger fluorescence due to the suppression of photoisomerization by intramolecular hydrogen bond. Furthermore, upon reduction, these azobenzene derivatives exhibit fluorescence transformation from red to green. These new azobenzene derivatives with AIE attributes and stimuli-responsiveness are expected to provide a new platform for developing photo-responsive luminescent materials.

KW - Azobenzene

KW - Fluorescence

KW - Intramolecular hydrogen bond

KW - Photoisomerization

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U2 - 10.1016/j.dyepig.2023.111662

DO - 10.1016/j.dyepig.2023.111662

M3 - 文章

AN - SCOPUS:85169782307

SN - 0143-7208

VL - 220

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 111662

ER -

Construction of emissive azobenzene derivatives by hydroxylation and aggregation

Abstract

Keywords

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