Reaction of Zn(II) with a BINOL-amino-acid Schiff base: An unusual off-on-off fluorescence response

TETRAHEDRON LETTERS

卷:59

Article

Wang, Xinjing¹  Shi, Dan¹  Xu, Yimang¹  Yu, Shanshan¹  Zhao, Feng¹  Wang, Yachen¹  Hu, Lingling¹  Tian, Jun¹  Yu, Xiaoqi¹  Pu, Lin^1,2 

[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China

[2] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

关键词: Fluorescence sensor;    Zinc;    BINOL;    Schiff base;    Amino acid;   

DOI  :  10.1016/j.tetlet.2018.04.069

来源: Elsevier

【 摘 要 】

An amino-acid based Schiff base (S)-2 is prepared from the condensation of (S)-3,3'-diformyl BINOL (BINOL = l,1'-bi-2-naphthol) with L-valine in the presence of tetrabutylammonium hydroxide in methanol. This compound is found to exhibit off-on-off fluorescence response toward Zn2+. The spectroscopic studies reveal that (S)-2 reacts with 1 equiv Zn2+ to form a dimeric [2+2] complex with greatly enhanced fluorescence. Excess amount of Zn2+ might cause dissociation of this dimeric complex to give significantly reduced fluorescence. (C) 2018 Elsevier Ltd. All rights reserved.

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