Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties

doi:10.6023/cjoc201710017

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1119-1125.DOI: 10.6023/cjoc201710017 Previous Articles Next Articles

Special Issue: 有机超分子化学合辑

Articles

“马鞍型”环八四噻吩-三嗪体系的合成与聚集诱导发光(AIE)性质研究

张卫杰^a, 徐莉^b, 宋金生^a, 马志英^a, 王华^a

a 河南大学纳米材料工程研究中心开封 475004;
b 河南大学化学化工学院开封 475004

收稿日期:2017-10-16 修回日期:2018-02-08 发布日期:2018-02-11
通讯作者: 马志英,E-mail:mazy11@henu.edu.cn;王华,E-mail:hwang@henu.edu.cn E-mail:mazy11@henu.edu.cn;hwang@henu.edu.cn
基金资助:
国家自然科学基金（Nos.21672053，21672054，21703055）及河南省有机功能材料创新团队（No.C20150011）资助项目.

Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties

Zhang Weijie^a, Xu Li^b, Song Jinsheng^a, Ma Zhiying^a, Wang Hua^a

a Research Center for Nanomaterials, Henan University, Kaifeng 475004;
b College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004

Received:2017-10-16 Revised:2018-02-08 Published:2018-02-11
Contact: 10.6023/cjoc201710017 E-mail:mazy11@henu.edu.cn;hwang@henu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21672053, 21672054, 21703055), and the Innovation Scientists and Technicians Troop Construction Projects of Henan Province (No. C20150011).

1. Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties.PDF(1368KB)

Abstract

With saddle-shaped cyclooctatetrathiophene (COTh) and 1, 3, 5-triazine as building blocks, three derivatives bearing one, two and three COTh units are synthesized via Kumada-typed reaction. Theoretical calculations indicate that the two absorption peaks in long wavelength region are derived from intramolecular charge transfer (CT) absorption. 2, 4- Di(methoxyl)-6-(5, 8, 11-tris(trimethylsilyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (1), 2-meth- oxyl-4, 6-di(5, 8, 11-tris(trimethyl-silyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (2) and 2, 4, 6-tris- (5, 8, 11-tris(trimethylsilyl)cycloocta [1, 2-b:4, 3-b':5, 6-b":8, 7-b'"]tetrathiophen-2-yl)-1, 3, 5-triazine (3) exhibit intramolecular charge transfer (ICT) state emission peaked in region of 560～570 nm in solution at room temperature, and give both local emission of COTh peaked at 400 nm and ICT state emission peaked in region of 480～500 nm in rigid solution at 77 K. In tetrahydrofuran (THF)-H₂O binary solvent system, compounds 1, 2 and 3 show typical aggregation induced emissions (AIE), which may be controlled by mechanism of restriction of intramolecular rotations (RIR) and restriction of intramolecular vibration (RIV). Crystal structure of 1 shows that intramolecular two rings of triazine and its linked thiophene are planar. There are strong C-C interactions between intermolecular rings of triazine and thiophene, which restrict the intramolecular rotation between triazine and thiophene rings. Such intermolecular C-C interactions are helpful to decrease the process of non-irradiative decay and increase AIE emission.

Key words: cyclooctatetrathiophene, 1, 3, 5-triazine, crystal structure, aggregation induced emission

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Zhang Weijie, Xu Li, Song Jinsheng, Ma Zhiying, Wang Hua. Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties[J]. Chin. J. Org. Chem., 2018, 38(5): 1119-1125.

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“马鞍型”环八四噻吩-三嗪体系的合成与聚集诱导发光(AIE)性质研究

Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties

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