Quinoline-derived electron-donating/withdrawing fluorophores for hydrazine detection and applications in environment and bioimaging

Kanagaraj Rajalakshmi; Selvaraj Muthusamy; Ho-Jin Lee; Palanisamy Kannan; Dongwei Zhu; Rathna Silviya Lodi; Meng Xie; Jimin Xie; Jong-Won Song; Yuanguo Xu

doi:10.1016/j.saa.2023.123282

Quinoline-derived electron-donating/withdrawing fluorophores for hydrazine detection and applications in environment and bioimaging

Spectrochim Acta A Mol Biomol Spectrosc. 2024 Jan 5:304:123282. doi: 10.1016/j.saa.2023.123282. Epub 2023 Aug 19.

Authors

Affiliations

¹ School of Chemistry and Chemical Engineering, School of Pharmacy, Jiangsu University, Zhenjiang 212013, China.
² School of Chemistry and Chemical Engineering, School of Pharmacy, Jiangsu University, Zhenjiang 212013, China. Electronic address: rajselva311@ujs.edu.cn.
³ Department of Natural Sciences, Southwest Tennessee Community College, Memphis, TN 38134, USA.
⁴ College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, PR China. Electronic address: ktpkannan@zjxu.edu.cn.
⁵ Department of Laboratory Medicine, The Affiliated People's Hospital and Department of Immunology, Jiangsu Key Laboratory of Laboratory Medicine, School of Medicine, Jiangsu University, Zhenjiang 212013, China.
⁶ Shandong Academy of Agricultural Science, Jinan China.
⁷ Department of Chemistry Education, Daegu University, Daegudae-ro 201, Gyeongsan-si, Gyeongsangbuk-do 38453, Republic of Korea. Electronic address: sjoshua@daegu.ac.kr.
⁸ School of Chemistry and Chemical Engineering, School of Pharmacy, Jiangsu University, Zhenjiang 212013, China. Electronic address: xuyg@ujs.edu.cn.

PMID: 37657372
DOI: 10.1016/j.saa.2023.123282

Abstract

Substitution can be employed to competently tune the photophysical properties of chemosensors. The effect of substituents on the absorption and emission properties of quinoline probes was investigated. Therefore, salicylaldehyde (S), N-diethylamino-salicylaldehyde (D), and nitro-salicylaldehyde (W)-based quinoline Schiff base derivatives were investigated with hydrazine and studied for their photophysical properties. The nucleophilic substitution reaction was used as a sensing mechanism between the probes and hydrazine and investigated with ¹H NMR, HR-MS characterizations, and DFT calculations. The sensitivity of QW-R is greater than that of QS-R and QD-R because of the stronger intramolecular charge transfer (ICT) in QW-R. The calculated LOD values are 28 nM for QS-R, 30 nM for QD-R, and 9 nM for QW-R. The probes were employed to monitor gaseous hydrazine using a smartphone and analyze solution forms of hydrazine in soil, water, and food samples, and living cells. Moreover, the in situ hydrazine release was monitored with bioimaging by administering an isoniazid drug. Significantly, the electronic effect of substituents over fluorescence showing, ranging from electron-donating to electron-withdrawing was investigated. We anticipate that this approach may be a promising strategy for the rational design of fluorescent sensors.

Keywords: 4-dintrobenzoate; Intramolecular charge transfer; Isoniazid-hydrazine; Nucleophilic substitution; Quinoline-2; Soil samples.