具有AIE和ESIPT双重性质的荧光分子的合成及光物理性质初探

引用本文: 刘思阳, 孙宇, 李云妍, 张岩. 具有AIE和ESIPT双重性质的荧光分子的合成及光物理性质初探[J]. 大学化学, 2023, 38(4): 269-276. doi: 10.3866/PKU.DXHX202211042 shu

Citation: Siyang Liu, Yu Sun, Yunyan Li, Yan Zhang. Synthesis and Photophysical Properties of Fluorescent Molecules with Aggregation-Induced Emission and Excited-State Intramolecular Proton Transfer Properties[J]. University Chemistry, 2023, 38(4): 269-276. doi: 10.3866/PKU.DXHX202211042 shu

具有AIE和ESIPT双重性质的荧光分子的合成及光物理性质初探

重庆师范大学化学学院, 重庆 401331

通讯作者: 张岩, yanzhang@cqnu.edu.cn

基金项目:
重庆市教委科学技术研究项目(KJQN202100502)

摘要: 化学实验训练是化学专业教学中不可或缺的一环，但陈旧的实验方案在一定程度上限制了学生的探索和创新精神。本实验方案深入结合科学前沿的热门领域，利用羰基的亲核加成反应，制备了一种具有聚集诱导发光(AIE)和激发态分子内质子转移(ESIPT)性质的荧光小分子。实验研究了该分子的基本光物理性质及酸碱刺激响应能力。整个反应过程不使用有毒或危险性试剂，反应物只需在乙醇中回流0.5 h即可完成，充分体现绿色有机合成的策略。实验过程紧凑有序，现象明显且荧光色彩变化丰富，能够更好地激发学生的实验热情。同时，本实验充分融合了有机合成基本操作及核磁共振、红外光谱、紫外可见吸收光谱、荧光光谱等多种现代分析和表征方法，是一个直观有效的开放性实验，可有效提升学生的专业综合素质、培养学生的创新性研究能力。

关键词:

English

Synthesis and Photophysical Properties of Fluorescent Molecules with Aggregation-Induced Emission and Excited-State Intramolecular Proton Transfer Properties

College of Chemistry, Chongqing Normal University, Chongqing 401331, China

Corresponding author: Yan Zhang, yanzhang@cqnu.edu.cn

Received Date: 15 November 2022

Abstract: Chemistry laboratory training is an integral part of chemistry teaching. However, outdated experimental protocols present limitations and can hinder students’ initiative and innate inclination toward exploration. In this study, novel scientific concepts were translated into experimental chemistry teaching. Small fluorescent molecules with aggregation-induced emission and excited-state intramolecular proton transfer properties were prepared using a carbonyl nucleophile addition reaction. The basic photophysical properties of the molecules and their fluorescence response to acid-base stimulation were evaluated experimentally. The non-toxic and non-noxious reagents used for the experiments were refluxed in ethanol for 0.5 h to implement green organic synthesis principles. The experiment was compact and the fluorescence and color changes of the as-synthesized molecules were conspicuous and remarkable. This can stimulate students’ enthusiasm for experimental chemistry. In addition to the basic organic synthesis reaction, this experiment included several modern analysis and characterization methods, such as nuclear magnetic resonance, Fourier-transform infrared spectroscopy, ultraviolet-visible absorption spectroscopy, and fluorescence spectroscopy. We are confident that this intuitive and effective basic experiment can effectively stimulate and cultivate the innate curiosity of students.

Key words:

Aggregation-induced emission
/ Excited-state intramolecular proton transfer
/ Green chemistry
/ Salicylide
/ p-phenylenediamine

1. [1]
  Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; et al. Chem. Commun. 2001, 1740.Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; et al. Chem. Commun. 2001, 1740.
2. [2]
  Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718.Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718.
3. [3]
  Yan, D.; Wu, Q.; Wang, D.; Tang, B. Z. Angew. Chem. Int. Ed. 2018, 60, 15724.Yan, D.; Wu, Q.; Wang, D.; Tang, B. Z. Angew. Chem. Int. Ed. 2018, 60, 15724.
4. [4]
  Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361.Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361.
5. [5]
  Mei, J.; Hong, Y.; Lam, J. W. Y.; Qin, A.; Tang, Y.; Tang, B. Z. Adv. Mater. 2014, 26, 5429.Mei, J.; Hong, Y.; Lam, J. W. Y.; Qin, A.; Tang, Y.; Tang, B. Z. Adv. Mater. 2014, 26, 5429.
6. [6]
  Weller, A. Naturwissenschaften 1955, 42, 175.Weller, A. Naturwissenschaften 1955, 42, 175.
7. [7]
  Weller, A. Elektrochem. 1956, 60, 1144.Weller, A. Elektrochem. 1956, 60, 1144.
8. [8]
  Sedgwick, A. C.; Wu, L.; Han, H.-H.; Bull, S. D.; He, X.-P.; James, T. D.; Sessler, J. L.; Tang, B. Z.; Tian, H.; Yoon, J. Chem. Soc. Rev. 2018, 47, 8842.Sedgwick, A. C.; Wu, L.; Han, H.-H.; Bull, S. D.; He, X.-P.; James, T. D.; Sessler, J. L.; Tang, B. Z.; Tian, H.; Yoon, J. Chem. Soc. Rev. 2018, 47, 8842.
9. [9]
  Zhou, P. W.; Han, K. L. Acc. Chem. Res. 2018, 51, 1681.Zhou, P. W.; Han, K. L. Acc. Chem. Res. 2018, 51, 1681.
10. [10]
  Song, Z.; Kwok, R. T. K.; Zhao, E.; He, Z.; Hong, Y.; Lam, J. W. Y.; Liu, B.; Tang, B. Z. ACS Appl. Mater. Interfaces 2014, 6, 17245.Song, Z.; Kwok, R. T. K.; Zhao, E.; He, Z.; Hong, Y.; Lam, J. W. Y.; Liu, B.; Tang, B. Z. ACS Appl. Mater. Interfaces 2014, 6, 17245.
11. [11]
  Biswas, S.; Mengji, R.; Barman, S.; Venugopal, V.; Jana, A.; Singh, N. D. P. Chem. Commun. 2018, 54, 168.Biswas, S.; Mengji, R.; Barman, S.; Venugopal, V.; Jana, A.; Singh, N. D. P. Chem. Commun. 2018, 54, 168.
12. [12]
  Tsutsui, Y.; Zhang, W.; Ghosh, S.; Sakurai, T.; Yoshida, H.; Ozaki, M.; Akutagawa, T.; Seki, S. Adv. Opt. Mater. 2020, 8, 1902158.Tsutsui, Y.; Zhang, W.; Ghosh, S.; Sakurai, T.; Yoshida, H.; Ozaki, M.; Akutagawa, T.; Seki, S. Adv. Opt. Mater. 2020, 8, 1902158.
13. [13]
  李嘉梁, 汪博宇, 付薪宇, 宋志光, 朱万春, 范勇, 马强, 郭玉鹏. 大学化学, 2020, 35 (4), 60.
14. [14]
  赵梦龙, 苑岱雷, 叶梓, 房芳, 于月娜. 大学化学, 2022, 37 (5), 2109108.

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沈阳化工大学材料科学与工程学院沈阳 110142

具有AIE和ESIPT双重性质的荧光分子的合成及光物理性质初探

通讯作者: 张岩, yanzhang@cqnu.edu.cn

English

Synthesis and Photophysical Properties of Fluorescent Molecules with Aggregation-Induced Emission and Excited-State Intramolecular Proton Transfer Properties

Corresponding author: Yan Zhang, yanzhang@cqnu.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

具有AIE和ESIPT双重性质的荧光分子的合成及光物理性质初探

通讯作者: 张岩, yanzhang@cqnu.edu.cn

English

Synthesis and Photophysical Properties of Fluorescent Molecules with Aggregation-Induced Emission and Excited-State Intramolecular Proton Transfer Properties

Corresponding author: Yan Zhang, yanzhang@cqnu.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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