Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(5): 1119-1125. doi: 10.6023/cjoc201710017 shu

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

Corresponding author: Ma Zhiying, mazy11@henu.edu.cn Wang Hua, hwang@henu.edu.cn
Received Date: 16 October 2017
Revised Date: 8 February 2018
Available Online: 11 May 2018
Fund Project: the National Natural Science Foundation of China 21672054Project 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)the National Natural Science Foundation of China 21703055the National Natural Science Foundation of China 21672053the Innovation Scientists and Technicians Troop Construction Projects of Henan Province C20150011

Figures(6)

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.
- cyclooctatetrathiophene,
- 1, 3, 5-triazine,
- crystal structure,
- aggregation induced emission
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