An o-hydroxyl aldehyde structure based naphthalimide derivative: Reversible photochromic properties and its application in ClO- detection in living cells

Xinxue Tang; Hao Sun; Jing Nie; Xiang'en Han; Yun Zhao; Ran Zhang; Zhonghai Ni

doi:10.1016/j.saa.2019.04.049

An o-hydroxyl aldehyde structure based naphthalimide derivative: Reversible photochromic properties and its application in ClO^- detection in living cells

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Aug 5:219:154-163. doi: 10.1016/j.saa.2019.04.049. Epub 2019 Apr 22.

Authors

Xinxue Tang¹, Hao Sun¹, Jing Nie¹, Xiang'en Han², Yun Zhao¹, Ran Zhang¹, Zhonghai Ni³

Affiliations

¹ School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou 221116, People's Republic of China.
² School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou 221116, People's Republic of China. Electronic address: xiangenh@163.com.
³ School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou 221116, People's Republic of China. Electronic address: nizhonghai@cumt.edu.cn.

PMID: 31035125
DOI: 10.1016/j.saa.2019.04.049

Abstract

A bifunctional organic compound 2-butyl-6-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de] isoquinoline-5-carbaldehyde (BHC) with photochromic properties in solid state and probe detection for ClO^- in complete water solution was synthesized and fully characterized. A 'white-yellow-white' reversible photochromic behavior could be observed when alternating UV/vis light irradiation on the solid BHC powder. Good fatigue resistance and adjustable bleaching rate were shown when heating conditions changes. In addition, BHC displayed a high selectivity and low detection limit (1.16 × 10^-8 M) for ClO^-. The photoluminescent fluorescence "on-off" recognition result can be easily identified and BHC has been tested for safely imaging living cells and detecting hypochlorite anion in vitro and vivo. A better water solubility of BHC effectively reduces damage caused by organic solvent in cell imaging progress.

Keywords: Cell imaging; ClO(−) detection; Fatigue resistance; Reversible photochromic; Water solubility.

MeSH terms

Aldehydes / chemistry*
Anions / analysis
Fluorescence
Fluorescent Dyes / chemistry*
HeLa Cells
Humans
Hypochlorous Acid / analysis*
Isoquinolines / chemistry*
Models, Molecular
Naphthalimides / chemistry*
Optical Imaging / methods

Substances

Aldehydes
Anions
Fluorescent Dyes
Isoquinolines
Naphthalimides
Hypochlorous Acid