Synthesis and Application of Specific N2H4 Fluorescent Probes with AIE Effect Based on Pyrazole Structure

Yun-Shang Yang; Zhen Zhang; Ying-Peng Zhang; Yu-Ning Liang; Xing-Xing Li; Zhi-Dong Teng

doi:10.1007/s10895-024-03695-9

Synthesis and Application of Specific N₂H₄ Fluorescent Probes with AIE Effect Based on Pyrazole Structure

J Fluoresc. 2024 Apr 19. doi: 10.1007/s10895-024-03695-9. Online ahead of print.

Authors

Yun-Shang Yang¹, Zhen Zhang², Ying-Peng Zhang³, Yu-Ning Liang², Xing-Xing Li², Zhi-Dong Teng⁴

Affiliations

¹ School of Petrochemical Engineering & Key Laboratory of Low Carbon Energy and Chemical Engineering of Gansu, Lanzhou University of Technology, Lanzhou, 730050, China. yangyunshang@tom.com.
² School of Petrochemical Engineering & Key Laboratory of Low Carbon Energy and Chemical Engineering of Gansu, Lanzhou University of Technology, Lanzhou, 730050, China.
³ School of Petrochemical Engineering & Key Laboratory of Low Carbon Energy and Chemical Engineering of Gansu, Lanzhou University of Technology, Lanzhou, 730050, China. yingpengzhang@126.com.
⁴ State Key Laboratory of Veterinary Etiological Biology and Key Laboratory of Animal Virology of Ministry of Agriculture, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Lanzhou, 730046, China. tengzhidong@caas.cn.

PMID: 38639858
DOI: 10.1007/s10895-024-03695-9

Abstract

Two fluorescent probes, Y_1-2 were synthesized from 2-acetonaphthone, 4-acetylbiphenyl, and phenyl hydrazine by Vilsmeier-Haack reaction and Knoevenagel condensation. Their recognition efficacies for N₂H₄ were tested by UV-visible absorption spectroscopy and fluorescence emission spectroscopy. The recognition mechanism were studies by density-functional theory calculations, and the effect of pH on N₂H₄ recognition was also studied. The results showed that the probe Y_1-2 has high selectivity and a low detection limit for N₂H₄, and the recognition of N₂H₄ can be accomplished at physiological pH. The probes have had obvious aggregation-induced luminescence effect, large Stokes shift, high sensitivity, and can be successfully applied to live cell imaging.

Keywords: AIE effect; Cell imaging; N2H4 recognition; Pyrazole.