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
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