Design, synthesis and application in biological imaging of a novel red fluorescent dye based on a rhodanine derivative

Zijing Li; Bin Huang; Yuan Wang; Wenbo Yuan; Yijing Wu; Ruitao Yu; Guichuan Xing; Taotao Zou; Youtian Tao

doi:10.1039/d0ra08998b

Design, synthesis and application in biological imaging of a novel red fluorescent dye based on a rhodanine derivative

RSC Adv. 2020 Dec 23;11(1):160-163. doi: 10.1039/d0ra08998b. eCollection 2020 Dec 21.

Authors

Zijing Li¹, Bin Huang², Yuan Wang³, Wenbo Yuan¹, Yijing Wu¹, Ruitao Yu¹, Guichuan Xing⁴, Taotao Zou³, Youtian Tao¹

Affiliations

¹ Key Laboratory of Flexible Electronics, Institute of Advanced Materials, Nanjing Tech University Nanjing P. R. China iamyttao@njtech.edu.cn.
² College of Life Sciences and Chemistry, Jiangsu Key Laboratory of Biofunctional Molecule, Jiangsu Second Normal University Nanjing P. R. China huangbinhb31@sina.com.
³ Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University Guangzhou P. R. China zoutt3@mail.sysu.edu.cn.
⁴ Institute of Applied Physics and Materials Engineering, University of Macau Macao SAR 999078 China gcxing@um.edu.mo.

Abstract

A novel acceptor-donor-acceptor type molecule, namely 2-triphenylamine-1,3-dia[2-(3-ethyl-4-oxo-thiazolidin-2-ylidene)-malononitrile] (2RDNTPA), is designed and synthesized. 2RDNTPA exhibits a large Stokes shift of 244 nm and red fluorescence emission of 629 nm with a decent photoluminescence quantum yield of 13%. Furthermore, as a potential red fluorescent dye, 2RDNTPA can be applied in fluorescence imaging of living cancer cells (HepG2) with negligible cytotoxicity and a half maximal inhibitory concentration much more than 100 μM.