Design and Synthesis of Novel Aggregation-Induced Luminescence Molecules Based on Isoquinoline

doi:10.6023/cjoc202204038

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3776-3783.DOI: 10.6023/cjoc202204038 Previous Articles Next Articles

ARTICLES

基于异喹啉骨架结构的新型聚集诱导发光分子的设计与合成

谭佳敏^a, 余雅君^a, 关猛^a, 赵云辉^a^,^*(), 唐子龙^b, 周智华^a, 郭涛^c^,^*()

^a湖南科技大学化学化工学院精细聚合物可控制备及功能应用湖南省重点实验室湖南湘潭 411201
^b湖南科技大学理论有机化学与功能分子教育部重点实验室湖南湘潭 411201
^c河南工业大学化学化工学院郑州 450001

收稿日期:2022-04-15 修回日期:2022-06-18 发布日期:2022-07-13
通讯作者: 赵云辉, 郭涛
基金资助:
国家自然科学基金(21877034); 湖南省自然科学基金(2020JJ4028); 湖南省科技创新计划(2021RC5028); 河南省科技攻关(212102210202)

Design and Synthesis of Novel Aggregation-Induced Luminescence Molecules Based on Isoquinoline

Jiamin Tan^a, Yajun Yu^a, Meng Guan^a, Yunhui Zhao^a(), Zilong Tang^b, Zhihua Zhou^a, Tao Guo^c()

^aHunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201
^bKey Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education, Hunan University of Science and Technology, Xiangtan, Hunan 411201
^cSchool of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001

Received:2022-04-15 Revised:2022-06-18 Published:2022-07-13
Contact: Yunhui Zhao, Tao Guo
Supported by:
National Natural Science Foundation of China(21877034); Natural Science Foundation of Hunan Provincial(2020JJ4028); Postgraduate Scientific Research Innovation Project of Hunan Province(2021RC5028); Science and Technology Foundation of Henan Province(212102210202)

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Abstract

Aggregation induced emission (AIE) molecules have been widely used in chemistry, biosensor, cell imaging and organic light-emitting diode (OLED) due to their excellent spectral properties. It was found for the first time that isoquinoline benzoxazine molecules exhibited good fluorescent emission in a high proportion of water/acetonitrile mixed solution, showing an obvious AIE phenomenon. On this basis, a novel type of AIE molecules fused with tetraphenylene and isoquinoline structural units were designed and synthesized. They were found exhibiting an excellent AIE phenomenon. It was confirmed by density functional theory (DFT) calculations that the splicing of the two structural units effectively reduced the energy gap of the frontier orbitals, which was helpful for the preparation of fluorescent molecules with longer emission wavelengths. In this study, AIE molecules based on the isoquinoline structure were discovered and prepared, which enriched the members of the AIE family. The AIE molecules based on the isoquinoline structure were first discovered and prepared in this study, which enriched the members of the AIE family.

Key words: isoquinoline, aggregation-induced emission, fluorescence, synthesis

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Jiamin Tan, Yajun Yu, Meng Guan, Yunhui Zhao, Zilong Tang, Zhihua Zhou, Tao Guo. Design and Synthesis of Novel Aggregation-Induced Luminescence Molecules Based on Isoquinoline[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3776-3783.

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Fig. & Tab. 7

Figure 1. Isoquinoline benzoxazine compound

Figure 2. (a) Fluorescence intensity of the compound 1h (10 μmol/L) in the solvent system with 0~99% water content; (b) the fluorescence intensity of compounds 1a~1j (10 μmol/L) in MeCN/H2O (V∶V=1∶99) (λex=340 nm)

Figure 3. Synthetic route of isoquinoline-based tetraphenyl ethylene AIE molecules

Figure 4. Isoquinoline-based tetraphenyl ethylene AIE molecules

Figure 5. (a) Fluorescence intensity of compound 7e in solvents containing 10%~99% water (λex=380 nm); (b) the fluorescence emission of compounds 7a~7e (the centrifugal tubes are 7a~7e from left to right)

Figure 6. (a) HOMO-LUMO gap of 1h (left) and 7e (right) calculated at the B3LYP/6-31G; (b) the fluorescence emission of compounds 1h and 7e

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基于异喹啉骨架结构的新型聚集诱导发光分子的设计与合成

Design and Synthesis of Novel Aggregation-Induced Luminescence Molecules Based on Isoquinoline

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