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

doi:10.6023/cjoc202204038

有机化学 ›› 2022, Vol. 42 ›› Issue (11): 3776-3783.DOI: 10.6023/cjoc202204038 上一篇下一篇

研究论文

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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摘要/Abstract

聚集诱导发光(AIE)分子因其优异的光谱性能已广泛应用于化学、生物传感器、细胞成像和有机发光二极管(OLED)等研究领域. 发现异喹啉并苯并噁嗪分子在高比例水/乙腈混合溶液中有着良好的荧光发射, 呈现明显的AIE现象. 在此基础上, 继续设计、合成了一类融合四苯乙烯和异喹啉结构单元的新型AIE分子, 研究发现该类分子亦具有良好的AIE现象. 通过密度泛函理论(DFT)计算证实了两个结构单元的拼接有效地降低了前线轨道的能隙, 有助于制备发射波长更长的荧光分子. 该研究首次发现并制备了基于异喹啉结构的AIE分子, 丰富了AIE家族成员.

关键词: 异喹啉, 聚集诱导发光, 荧光, 合成

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

引用此文

谭佳敏, 余雅君, 关猛, 赵云辉, 唐子龙, 周智华, 郭涛. 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[J]. 有机化学, 2022, 42(11): 3776-3783.

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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图/表 7

图1. 异喹啉并苯并噁嗪化合物.

Figure 1. Isoquinoline benzoxazine compound

图2. (a) 化合物1h (10 μmol/L)在0~99%水含量的溶剂体系中的荧光强度变化; (b)化合物1a~1j (10 μmol/L)在MeCN/H2O (V∶V=1∶99)溶剂体系中的荧光强度(λex=340 nm)

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)

图3. 异喹啉基四苯乙烯型AIE分子的合成路线

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

图4. 异喹啉基四苯乙烯型AIE分子

Figure 4. Isoquinoline-based tetraphenyl ethylene AIE molecules

图5. (a)化合物7e在10%~99%水含量的溶剂体系中的荧光强度变化(λex=380 nm); (b)化合物7a~7e的荧光发射(离心管从左到右依次为7a~7e)

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)

图6. (a) 1h和7e的优化结构及前沿分子轨道结构; (b) 1h和7e的荧光发射

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

Figure 7. (a)异喹啉并苯并咪唑化合物8的荧光性能; (b)分子扭转示意图; (c) 1h与7e的模拟分子结构 (a) Fluorescent properties of 6-phenylbenzo[4,5]imi- dazo[2,1-a]isoquinoline 8 (λex=360 nm); (b) the molecular torsion diagram of compound 1a and 8; (c) the simulated molecular structure of 1h与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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