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A novel Schiff base macrocycle based on 1,1′‐binaphthyl for fluorescence recognition
Author(s) -
Tokunaga Hiroki,
Kazama Kotoha,
Tsuboi Masaki,
Miyasaka Makoto
Publication year - 2021
Publication title -
luminescence
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.428
H-Index - 45
eISSN - 1522-7243
pISSN - 1522-7235
DOI - 10.1002/bio.4101
Subject(s) - schiff base , fluorescence , chemistry , metal ions in aqueous solution , metal , derivative (finance) , polyamine , condensation , proton nmr , photochemistry , crystallography , stereochemistry , organic chemistry , biochemistry , physics , quantum mechanics , financial economics , economics , thermodynamics
A novel chiral polyimine macrocycle C‐1 was designed and synthesized by the self‐condensation of the dialdehyde of the chiral dinaphtho[ 2,1‐d:1′,2′‐f ][1,3]dioxepine derivative and o ‐phenylenediamine by Schiff base formation, and the corresponding polyamine macrocycle C‐1H was obtained by the reduction of the polyimine macrocycle. The UV–vis and fluorescence spectral studies indicated that both C‐1 and C‐1H form the complex with metal ions in a 1:2 ratio. The fluorescence behaviour of C‐1 upon the addition of Zn 2+ or Cd 2+ showed a ‘turn‐on’ response accompanied by fluorescence enhancement at 510 nm six times for Cd 2+ and 13 times for Zn 2+ . In contrast, C‐1H revealed a ‘turn‐off’ response upon the addition of Co 2+ , Ni 2+ , and Cu 2+ .