A novel Schiff base macrocycle based on 1,1'-binaphthyl for fluorescence recognition

Abstract

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 Zn²⁺ or Cd²⁺ showed a 'turn-on' response accompanied by fluorescence enhancement at 510 nm six times for Cd²⁺ and 13 times for Zn²⁺ . In contrast, C-1H revealed a 'turn-off' response upon the addition of Co²⁺ , Ni²⁺ , and Cu²⁺ .

Keywords: BINOL derivative; fluorescence; macrocycle.