Citation: Kuan Deng, Fei Yang, Zhi-Qi Cheng, Bi-Wen Ren, Hua Liu, Jiao Chen, Meng-Yao She, Le Yu, Xiao-Gang Liu, Hai-Tao Feng, Jian-Li Li. Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle[J]. Chinese Chemical Letters, ;2024, 35(10): 109464. doi: 10.1016/j.cclet.2023.109464 shu

Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle

Kuan Deng ^{a, 1} ,
Fei Yang ^{b, 1} ,
Zhi-Qi Cheng ^a ,
Bi-Wen Ren ^b ,
Hua Liu ^a ,
Jiao Chen ^{a, b} ,
Meng-Yao She ^{a, b, *,} ,
Le Yu ^a ,
Xiao-Gang Liu ^c ,
Hai-Tao Feng ^d ,
Jian-Li Li ^{a, *,}

a.
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, Shaanxi Key Laboratory for Carbon Neutral Technology, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China
b.
Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education; Biomedicine Key Laboratory of Shaanxi Province, Lab of Tissue Engineering, the College of Life Sciences, Faculty of Life Science & Medicine, Northwest University, Xi'an 710069, China
c.
Fluorescence Research Group, Singapore University of Technology and Design, Singapore 487372, Singapore
d.
Baoji AIE Research Center, Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, China

shemengyao@nwu.edu.cn

lijianli@nwu.edu.cn

Received Date: 25 October 2023
Revised Date: 23 December 2023
Accepted Date: 26 December 2023
Available Online: 30 December 2023

Figures(4)

Dual-state emission (DSE) molecules displayed conspicuous fluorescent performance both in solid and solution states. However, the construction of DSE molecules and the regulation of their emission wavelengths remains a great challenge. Based on the structure-function relationship of quinolinonitrile-type fluorophores, this work proposed a feasible strategy for modulating their fluorescent properties into DSE via limiting the torsion angle between the quinoline ring and C=C bond in the range of 4.7° to 30°. Based on this strategy, 53 compounds were obtained which displayed tunable emission wavelengths from 397 nm to 740 nm in solid-state and from 360 nm to 672 nm in solution. The feasibility of the strategy was supported by a series of theoretical calculations, optical characterizations, and crystal analysis, suggesting the compounds have great potential in imaging living cells and tissues with desired wavelengths.
- Fluorescence,
- Dual-state emission,
- Structure-function relationship,
- Wavelength regulation,
- Fluorescent imaging
1. [1]
  Y. Qin, Q. Ling, Y. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202308210. doi: 10.1002/anie.202308210
2. [2]
  M. Dai, B. Zhou, X. Fang, et al., ACS Appl. Mater. Interfaces 14 (2022) 40223–40231. doi: 10.1021/acsami.2c11164
3. [3]
  Q. Xu, L. Ma, X. Lin, et al., Chin. Chem. Lett. 33 (2022) 2965–2968. doi: 10.1016/j.cclet.2021.12.097
4. [4]
  K. Ma, H. Yang, X. Wu, et al., Angew. Chem. Int. Ed. 62 (2023) e202301518. doi: 10.1002/anie.202301518
5. [5]
  L. Wang, J. Liu, M. Ren, et al., Chin. Chem. Lett. 35 (2024) 108945. doi: 10.1016/j.cclet.2023.108945
6. [6]
  C. Wang, W. Jiang, D. Tan, et al., Chem. Sci. 14 (2023) 4786–4795. doi: 10.1039/D2SC06710B
7. [7]
  Y. Chen, H. Zhang, Y. Liu, et al., ACS Sens. 8 (2023) 2359–2367. doi: 10.1021/acssensors.3c00470
8. [8]
  X. Tian, D. Wu, W. Wei, et al., Chin. Chem. Lett. 35 (2024) 108912. doi: 10.1016/j.cclet.2023.108912
9. [9]
  B. Li, H. Liu, Y. He, et al., Angew. Chem. Int. Ed. 61 (2022) e202200025. doi: 10.1002/anie.202200025
10. [10]
  Y. Yang, M. Ma, L. Shen, et al., Angew. Chem. Int. Ed. 62 (2023) e202310408. doi: 10.1002/anie.202310408
11. [11]
  X. Ma, Y. Huang, W. Chen, et al., Angew. Chem. Int. Ed. 62 (2023) e202216109. doi: 10.1002/anie.202216109
12. [12]
  Y. Chen, C. Xue, J. Wang, et al., Chin. Chem. Lett. 33 (2022) 1637–1642. doi: 10.1016/j.cclet.2021.09.088
13. [13]
  B. Huang, X. Liu, G. Yang, et al., CCS Chem. 4 (2021) 2090–2101.
14. [14]
  E. Feng, L. Jiao, S. Tang, et al., Chem. Eng. J. 432 (2022) 134355. doi: 10.1016/j.cej.2021.134355
15. [15]
  N. Ahmed, W. Zareen, Y. Ye, Chin. Chem. Lett. 33 (2022) 2765–2772. doi: 10.1016/j.cclet.2021.12.092
16. [16]
  J. Luo, Z. Xie, J.W.Y. Lam, et al., Chem. Commun. (2001) 1740–1741.
17. [17]
  L. Liu, C. Li, J. Gong, et al., Angew. Chem. Int. Ed. 62 (2023) e202307776. doi: 10.1002/anie.202307776
18. [18]
  T. Zhang, X. Chen, C. Yuan, et al., Angew. Chem. Int. Ed. 62 (2023) e202211550. doi: 10.1002/anie.202211550
19. [19]
  Z. Li, S. Chen, Y. Huang, et al., Chem. Eng. J. 450 (2022) 138087. doi: 10.1016/j.cej.2022.138087
20. [20]
  J.L. BelmonteVázquez, Y.A. AmadorSánchez, L.A. RodríguezCortés, et al., Chem. Mater. 33 (2021) 7160–7184. doi: 10.1021/acs.chemmater.1c02460
21. [21]
  L.A RodríguezCortés, A. NavarroHuerta, B. RodríguezMolina, Matter 4 (2021) 2622–2624. doi: 10.1016/j.matt.2021.06.023
22. [22]
  W. Dai, P. Liu, S. Guo, et al., ACS Appl. Bio Mater. 2 (2019) 3686–3692. doi: 10.1021/acsabm.9b00596
23. [23]
  M. Huang, J. Zhou, K. Xu, et al., Dyes Pigm. 160 (2019) 839–847. doi: 10.1016/j.dyepig.2018.08.066
24. [24]
  Y. Li, Y. Lei, L. Dong, et al., Chem. Eur. J. 25 (2019) 573–581. doi: 10.1002/chem.201804074
25. [25]
  Q. Qiu, P. Xu, Y. Zhu, et al., Chem. Eur. J. 25 (2019) 15983–15987. doi: 10.1002/chem.201903857
26. [26]
  X. Zhang, Y. Zhou, M. Wang, et al., Chem. Asian J. 15 (2020) 1692–1700. doi: 10.1002/asia.202000322
27. [27]
  X. Hu, A.C. Sedgwick, D.N. Mangel, et al., J. Am. Chem. Soc. 144 (2022) 7382–7390. doi: 10.1021/jacs.2c01155
28. [28]
  G. Chen, W. Li, T. Zhou, et al., Adv. Mater. 27 (2015) 4496–4501. doi: 10.1002/adma.201501981
29. [29]
  S. Qu, Q. Lu, S. Wu, et al., J. Mater. Chem. 22 (2012) 24605–24609. doi: 10.1039/c2jm35002e
30. [30]
  A. Shundo, Y. Okada, F. Ito, et al., Macromolecules 45 (2012) 329–335. doi: 10.1021/ma201901x
31. [31]
  H. Wu, Z. Chen, W. Chi, et al., Angew. Chem. Int. Ed. 58 (2019) 11419–11423. doi: 10.1002/anie.201906507
32. [32]
  X. Mei, J. Wang, Z. Zhou, et al., J. Mater. Chem. C 5 (2017) 2135–2141. doi: 10.1039/C6TC05519B
33. [33]
  D.C. Green, J. Ihli, P.D. Thornton, et al., Nat. Commun. 7 (2016) 13524. doi: 10.1038/ncomms13524
34. [34]
  T. Ma, T. Li, L. Zhou, et al., Nat. Commun. 11 (2020) 1811. doi: 10.1038/s41467-020-15600-6
35. [35]
  Z. Wang, X. Wang, S. Cong, et al., Nat. Commun. 11 (2020) 302. doi: 10.1038/s41467-019-14194-y
36. [36]
  C. Shi, Z. Guo, Y. Yan, et al., ACS Appl. Mater. Interfaces 5 (2013) 192–198. doi: 10.1021/am302466m
37. [37]
  L.G. Kuz’mina, A.G. Sitin, E.N. Gulakova, et al., Crystallogr. Rep. 56 (2011) 611–621. doi: 10.1134/S1063774511040110
38. [38]
  J.E. Nycz, K. Czyż, M. Szala, et al., J. Mol. Struct. 1106 (2016) 416–423. doi: 10.1016/j.molstruc.2015.11.011
39. [39]
  A. Shao, Z. Guo, S. Zhu, et al., Chem. Sci. 5 (2014) 1383–1389. doi: 10.1039/c3sc52783b
40. [40]
  W. Fu, C. Yan, Z. Guo, et al., J. Am. Chem. Soc. 141 (2019) 3171–3177. doi: 10.1021/jacs.8b12820
41. [41]
  F. Xiao, X. Liu, K. Lin, et al., J. Phys. Chem. C 125 (2021) 16792–16802. doi: 10.1021/acs.jpcc.1c04340
42. [42]
  M. Huang, R. Yu, K. Xu, et al., Chem. Sci. 7 (2016) 4485–4491. doi: 10.1039/C6SC01254J
43. [43]
  C. Maeda, T. Todaka, T. Ueda, et al., Chem. Eur. J. 22 (2016) 7508–7513. doi: 10.1002/chem.201505150
1. [1]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
2. [2]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
3. [3]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
4. [4]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
5. [5]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
6. [6]
  Peide Zhu , Yangjia Liu , Yaoyao Tang , Siqi Zhu , Xinyang Liu , Lei Yin , Quan Liu , Zhiqiang Yu , Quan Xu , Dixian Luo , Juncheng Wang . Bi-doped carbon quantum dots functionalized liposomes with fluorescence visualization imaging for tumor diagnosis and treatment. Chinese Chemical Letters, 2024, 35(4): 108689-. doi: 10.1016/j.cclet.2023.108689
7. [7]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
8. [8]
  Rui Cheng , Xin Huang , Tingting Zhang , Jiazhuang Guo , Jian Yu , Su Chen . Solid superacid catalysts promote high-performance carbon dots with narrow-band fluorescence emission for luminescence solar concentrators. Chinese Chemical Letters, 2024, 35(8): 109278-. doi: 10.1016/j.cclet.2023.109278
9. [9]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
10. [10]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
11. [11]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
12. [12]
  Bohan Zhang , Bingzhe Wang , Guichuan Xing , Zikang Tang , Songnan Qu . Regulation of the multi-emission centers in carbon dots via a bottom-up synthesis approach. Chinese Chemical Letters, 2024, 35(9): 109358-. doi: 10.1016/j.cclet.2023.109358
13. [13]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
14. [14]
  Ziyi Liu , Xunying Liu , Lubing Qin , Haozheng Chen , Ruikai Li , Zhenghua Tang . Alkynyl ligand for preparing atomically precise metal nanoclusters: Structure enrichment, property regulation, and functionality enhancement. Chinese Journal of Structural Chemistry, 2024, 43(11): 100405-100405. doi: 10.1016/j.cjsc.2024.100405
15. [15]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
16. [16]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
17. [17]
  Botao QU , Qian WANG , Xiaogang NING , Yuxin ZHOU , Ruiping ZHANG . Deeply penetrating photoacoustic imaging in tumor tissues based on dual-targeted melanin nanoparticle. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1025-1032. doi: 10.11862/CJIC.20230416
18. [18]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
19. [19]
  Peng Jia , Yunna Guo , Dongliang Chen , Xuedong Zhang , Jingming Yao , Jianguo Lu , Liqiang Zhang . In-situ imaging electrocatalysis in a solid-state Li-O₂ battery with CuSe nanosheets as air cathode. Chinese Chemical Letters, 2024, 35(5): 108624-. doi: 10.1016/j.cclet.2023.108624
20. [20]
  Yan Wang , Huixin Chen , Fuda Yu , Shanyue Wei , Jinhui Song , Qianfeng He , Yiming Xie , Miaoliang Huang , Canzhong Lu . Oxygen self-doping pyrolyzed polyacrylic acid as sulfur host with physical/chemical adsorption dual function for lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(7): 109001-. doi: 10.1016/j.cclet.2023.109001

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(118)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142