A Schiff base fluorescence probe for highly selective turn-on recognition of Zn2+. Issue 4 (25th January 2017)

• Record Type: Journal Article
• Authors: Zhu, Jinli; Zhang, Yuhuan; Chen, Yihan; Sun, Tongming; Tang, Yanfeng; Huang, Yang; Yang, Qingqing; Ma, Danyang; Wang, Yipu; Wang, Miao
• Is Part Of: Tetrahedron letters. Volume 58:Issue 4(2017)
• Page Start: 365
• Page End: 370
• Publication Date: 2017-01-25
• Subjects: Zn2+ detection -- Schiff base -- Turn-on fluorescence -- Live cells; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.12.041
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A simple Schiff-based fluorescence sensor for Zn 2+, was synthesized. This sensor was of good selectivity and sensitivity for Zn 2+, especially without the interference of Cd 2+ . This sensor can be used in live cells. Abstract: A simple Schiff baseCTS, synthesized between 2-hydroxy-1-naphthaldehyde and 2-benzylthio-ethanamine, was found to be a good turn-on fluorescence probe for the detection of Zn 2+, due to the restriction of the rotation of the bond between CN and naphthalene ring and/or the blocking of the photo-induced electron transfer (PET) mechanism of the nitrogen atom to naphthalene ring. Excellent selectivity for Zn 2+ was evidenced, over many other competing ions, including Fe 3+, Cr 3+, Ni 2+, Co 2+, Fe 2+, Mn 2+, Ca 2+, Hg 2+, Pb 2+, Cu 2+, Mg 2+, Ba 2+, Cd 2+, Ag +, Li +, K +, and Na +, in EtOH/HEPES buffer (95:5, v/v, pH = 7.4). It was noteworthy that Cd 2+ had no interference with Zn 2+ . The stoichiometric complex ofCTS -Zn 2+ was determined to be 2:1 forCTS and Zn 2+ in molar, based on the Job plot and single crystal X-ray diffraction data. The binding constant of the complex was 85.7 M −2 with a detection limit of 5.03 × 10 −7 M. The fluorescence bio-imaging capability ofCTS to detect Zn 2+ in live cells was also studied. These results indicated thatCTS could serve as a favorable probe for Zn 2+ .