给体-受体(D-A)型苯基环八四噻吩的合成及其聚集诱导发光与高压发光性能研究
收稿日期: 2024-04-01
修回日期: 2024-06-21
网络出版日期: 2024-07-10
基金资助
国家自然科学基金(U2004213); 国家自然科学基金(21672053); 河南省有机功能材料科技创新团队(C20150011)
Synthesis of Donor-Acceptor (D-A) Typed Phenylcyclooctatetrathiophenes and Their Performances on Aggregation Induced Emission and High Pressure Luminescence
Received date: 2024-04-01
Revised date: 2024-06-21
Online published: 2024-07-10
Supported by
National Natural Science Foundation of China(U2004213); National Natural Science Foundation of China(21672053); Organic Functional Materials Technology Innovation Team of Henan Province(C20150011)
“马鞍型”环八四噻吩(COTh)是一类有趣的聚集诱导发光(AIE)分子. 通过Suzuki反应, 将强吸电子基团氰基(CN)与强供电子基团甲氧基(OMe)引入到苯环的邻位、间位与对位, 构筑了6种取代苯基的给体-受体(D-A)型Ar-COTh化合物. p-OMe-Ph-COTh的单晶结构分析显示, 分子间存在多重S…C、C…O和O…H相互作用. 这些D-A型Ar-COTh化合物均表现出显著的AIE发光性质, 来源于COTh自身的分子内空间共轭效应(ITSC)所造成的较低能级的激发态发光, 发光峰位与取代基效应关联较小. 其固态发光的荧光量子产率高于AIE态发光. 高压下, 含强吸电子基团的p-CN-Ph-COTh随着压力从0.00 GPa到8.86 GPa的变化, 其荧光发射峰从531 nm红移到了634 nm, 二者相差达103 nm; 而含供电子基团的p-OMe-Ph-COTh随着压力从0.00 GPa到12.0 GPa的变化, 其发射峰只变化了29 nm, 体现出显著的取代基效应与高压发光性质.
关键词： 环八四噻吩(COTh); 给体-受体(D-A)化合物; 合成; 聚集诱导发光(AIE); 高压发光
杨玉杰 , 曹微 , 于际凯 , 张志霞 , 徐莉 , 王华 . 给体-受体(D-A)型苯基环八四噻吩的合成及其聚集诱导发光与高压发光性能研究[J]. 有机化学, 2024 , 44(8) : 2495 -2503 . DOI: 10.6023/cjoc202404001
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 donor-acceptor (D-A) typed substituted phenyl Ar-COTh compounds. The single crystal structure of p-OMe-Ph-COTh shows multiple intermolecular interactions, 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.
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