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+.

Fluorescent Schiff base sensors as a versatile tool for metal ion detection: strategies, mechanistic insights, and applications

“…3.2 Multi-metal ion sensors 57,[254][255][256][257][258][259][260][261][262][263][264] Nowadays, the development of sensors with multiple ion recognition sites is a challenging and emerging area of interest, because of the advantages of such systems such as cost reduction and faster analytical processing.…”

New Dinuclear Macrocyclic Copper(II) Complexes as Potentially Fluorescent and Magnetic Materials

“…A large number of donor atoms, such as O, N, S, P, and supramolecular construction, afford sufficient space for coordination atoms to create mono-, di-, and polynuclear complexes [17][18][19]. Macrocycle architecture consisting of a combination of binaphthyl groups can also show fluorescent properties.…”

Regio- and Enantioselective Macrocyclization from Dynamic Imine Formation: Chemo- and Enantioselective Fluorescent Recognition of Lysine

“…The dynamic covalent chemistry of imines has been actively utilized in the construction of materials of diverse structures such as macrocycles, cages, polymers, and covalent organic networks. − The reversible formation of imines from aldehydes and amines and the subsequent transiminations have allowed the development of many highly selective reaction processes for materials synthesis. C 2 - and C 3 -symmetric chiral diamines and triamines have been used to react with symmetric and achiral di- or polyaldehydes to make chiral macrocycles and cages. − Symmetric chiral dialdehydes have also been reacted with symmetric chiral diamines to make chiral macrocycles. − For example, racemic C 2 -symmetric chiral dialdehyde 1 was found to react with one enantiomer of the C 2 -symmetric chiral diamine 2 to generate a D 2 -symmetric chiral macrocycle 3 for the chirality-matched partners and a polymer for the mismatched ones (Scheme ). That is, an enantioselective condensation occurred to give the chiral macrocyclic product.…”