Synthesis of D-A Typed Phenylcyclooctatetrathiophenes and Their Performances on AIE and High Pressure Luminescence

doi:10.6023/cjoc202404001

Chinese Journal of Organic Chemistry

ARTICLE

D-A型苯基环八四噻吩的合成及其AIE与高压发光性能研究

杨玉杰^a, 曹微^b, 于际凯^b, 张志霞^a, 徐莉^*,a, 王华^*,b

^a河南大学化学与分子科学学院河南开封 475004;
^b河南大学纳米科学与工程研究院河南开封 475004

收稿日期:2024-04-01 修回日期:2024-06-21
基金资助:
国家自然科学基金(No. U2004213, 21672053)资助项目, 河南省有机功能材料科技创新团队项目(No. C20150011).

Synthesis of D-A Typed Phenylcyclooctatetrathiophenes and Their Performances on AIE and High Pressure Luminescence

Yang Yujie^a, Cao Wei^b, Yu Jikai^b, Xu Li^*,a, Wang Hua^*,b

^aCollege of Chemistry and Molecular Sciences, Henan University, Kaifeng, Henan 475004;
^bInstitute of Nanoscience and Engineerings, Henan University, Kaifeng, Henan 475004

Received:2024-04-01 Revised:2024-06-21
Contact: *E-mail: xuli@henu.edu.cn; hwang@henu.edu.cn
Supported by:
National Natural Science Foundation of China (Nos. U2004213, 21672053).

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Abstract

The saddle-shaped cyclooctatetrathiophene (COTh) is an interesting aggregation induced emission (AIE) molecule. In this work, the strong electron withdrawing group (-CN) and the strong electron donating group (-OMe) are introduced into the ortho, meta and para positions of benzene ring, reacting with COTh unit through Suzuki reaction to construct six D-A typed substituted phenyl Ar-COTh compounds. The single crystal structure of p-OMe-Ph-COTh shows multiple intermolecular interactons, such as S···C, C···O and O···H interactions among molecules. These D-A typed Ar-COThs exhibit significant AIE luminescence properties, which are mainly attributed to the intramolecular through space conjugation (ITSC) of COTh in excited state. The weak correlation between the emission peak and the substituent effect is observed. The fluorescence quantum yields of Ar-COThs in solid-state luminescence are higher than that of AIE state. Under high pressure, the emission peak of p-CN-Ph-COTh containing strong electron withdrawing group (-CN) showed strong bathochromic shift from 531 nm to 634 nm with a big difference of 103 nm under the external pressure change from 0.00 to 8.86 GPa; However, the emission peak of p-OMe-Ph-COTh containing electron donating group (-OMe) gave the only change of 29 nm under the pressure change from 0.00 to 12.0 GPa, demonstrating significant substituent and piezochromic effects.

Key words: Cyclooctatetrathiophene, D-A Compound, Synthesis, Aggregation-induced Emission (AIE), High Pressure Luminescence

Cite this article

Yang Yujie, Cao Wei, Yu Jikai, Xu Li, Wang Hua. Synthesis of D-A Typed Phenylcyclooctatetrathiophenes and Their Performances on AIE and High Pressure Luminescence[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202404001.

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D-A型苯基环八四噻吩的合成及其AIE与高压发光性能研究

Synthesis of D-A Typed Phenylcyclooctatetrathiophenes and Their Performances on AIE and High Pressure Luminescence

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