Synthesis of a New Amino-Furopyridine-Based Compound as a Novel Fluorescent pH Sensor in Aqueous Solution

Liyan Zhang; Yang Liu; Xiang Li; Yingjie Guo; Zhicheng Jiang; Tifeng Jiao; Jingyue Yang

doi:10.1021/acsomega.0c05734

Synthesis of a New Amino-Furopyridine-Based Compound as a Novel Fluorescent pH Sensor in Aqueous Solution

ACS Omega. 2021 Feb 5;6(7):4800-4806. doi: 10.1021/acsomega.0c05734. eCollection 2021 Feb 23.

Authors

Liyan Zhang¹, Yang Liu¹, Xiang Li², Yingjie Guo¹, Zhicheng Jiang¹, Tifeng Jiao^{1

3}, Jingyue Yang¹

Affiliations

¹ Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, 438West Hebei Street, Qinhuangdao 066004, P. R. China.
² Qinhuangdao Customs Technical Center, Qinhuangdao 066004, P. R. China.
³ State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, 438West Hebei Street, Qinhuangdao 066004, P. R. China.

Abstract

Development of new fluorescent molecules, especially pH-sensitive fluorescent dyes, is always in high demand due to their wide applications in various fields and the limited number of common chromophores. In this work, a family of 3-amino-N-phenylfuro[2,3-b]pyridine-2-carboxamides (AFP) was synthesized as novel fluorescent compounds. Besides fluorescence in an organic solvent, AFP 1 and AFP 2 exhibit good fluorescence properties in both acidic and basic aqueous solution, which could be explained by protonation or different conformations formed in solution. Density functional theory (DFT) calculations on the highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) of various conformations were performed for further support.