Role of Substitution Patterns in Four Regioisomeric Tetraphenylethylene-Thiophene Derivatives.

Shuai Hou, Hanxiao Tian, Ruiyao Li, Zishuai Huang, Dongyuan Zhu, Fan Xiao, Yunmeng Zhao, Jingjing Xu

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Article in Molecules (Basel, Switzerland), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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8 authors.

Shuai HouThe Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Frontiers Science Center of Biomimetic Catalysis, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China.

Hanxiao TianThe Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Frontiers Science Center of Biomimetic Catalysis, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China.

Ruiyao LiThe Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Frontiers Science Center of Biomimetic Catalysis, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China.

Zishuai HuangThe Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Frontiers Science Center of Biomimetic Catalysis, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China.

Dongyuan ZhuThe Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Frontiers Science Center of Biomimetic Catalysis, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China.

Fan XiaoThe Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Frontiers Science Center of Biomimetic Catalysis, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China.

Yunmeng ZhaoKey Laboratory of Smart Manufacturing in Energy Chemical Process, Ministry of Education, East China University of Science and Technology, Shanghai 200237, China.

Jingjing XuThe Education Ministry Key Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Frontiers Science Center of Biomimetic Catalysis, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China.ORCID 0000-0002-3838-624X

Funding

"111" Innovation and Talent Recruitment Base on Photochemical and Energy Materials D18020National Science Foundation of China 22305156Natural Science Foundation of Shanghai Municipality 22ZR1445900

6 · The paper itself

Abstract

Tetraphenylethylene (TPE)-thiophene compounds are promising candidates for stimuli-responsive luminescent materials, yet systematic investigations into the influence of substitution patterns on their photophysical properties remain limited. Herein, four regioisomeric TPE-thiophene derivatives have been synthesized by systematically varying the number and positions of TPE substituents on the thiophene core. A comprehensive spectroscopic characterization reveals that substitution patterns critically modulate the photoluminescence quantum yields (PLQYs). The ortho-monosubstituted isomer exhibits the highest PLQY (52.86% in solid state) compared with the meta-monosubstituted isomer (13.87% in solid state). Interestingly, thiophenes with two or three TPEs substituted at positions 2,5 or 2,3,5 have lower PLQYs, which is rare due to the common understanding that increasing the number of AIE parts should increase the PLQY. Further single-crystal structure analyses show that the key factor impacting the PLQY is the dihedral angles of the TPE subunit, which determines the degree of intramolecular twisting. This work establishes regiochemistry as a powerful design lever for tuning TPE-thiophene photophysics, offering underlying principles for the design of TPE-based thiophene molecules with high photoluminescent performance in the future.

Indexed as

aggregation-induced emissionPLQYsubstitution patterntetraphenylethylenethiophene

Identifiers

PMID40733219

DOI10.3390/molecules30142953

PMCPMC12298548

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