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

Hiroki Tokunaga¹, Kotoha Kazama², Masaki Tsuboi¹

¹Materials Science and Engineering, Graduate School of Engineering, Tokyo Denki University, 5 Senju-Asahi-cho, Adachi-ku, Tokyo, Japan.

Luminescence : the Journal of Biological and Chemical Luminescence

|June 8, 2021

Summary

A new chiral macrocycle C-1 and its reduced form C-1H were synthesized. These compounds selectively bind metal ions, with C-1 showing enhanced fluorescence for Zn2+ and Cd2+, and C-1H exhibiting fluorescence quenching for Co2+, Ni2+, and Cu2+.

Keywords:

BINOL derivative fluorescence macrocycle

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Area of Science:

Supramolecular Chemistry
Organic Synthesis
Coordination Chemistry

Background:

Chiral macrocycles are crucial in molecular recognition and sensing.
Schiff base chemistry enables the construction of complex macrocyclic architectures.
Developing selective metal ion sensors is vital for environmental and biological monitoring.

Purpose of the Study:

To design and synthesize a novel chiral polyimine macrocycle (C-1) and its corresponding polyamine (C-1H).
To investigate the metal ion complexation behavior of C-1 and C-1H using spectroscopic methods.
To explore the potential of these macrocycles as fluorescent sensors for specific metal ions.

Main Methods:

Synthesis of chiral polyimine macrocycle C-1 via Schiff base condensation.
Reduction of C-1 to the corresponding polyamine macrocycle C-1H.
UV-vis and fluorescence spectroscopy to study metal ion complexation.
Analysis of metal ion binding stoichiometry (1:2 ratio for both C-1 and C-1H).

Main Results:

C-1 exhibits a 'turn-on' fluorescence response for Zn2+ and Cd2+, with significant enhancement at 510 nm (6x for Cd2+, 13x for Zn2+).
C-1H displays a 'turn-off' fluorescence response upon addition of Co2+, Ni2+, and Cu2+ ions.
Both macrocycles form stable complexes with metal ions in a 1:2 ratio.

Conclusions:

The novel chiral macrocycles C-1 and C-1H demonstrate selective metal ion binding capabilities.
C-1 serves as an effective 'turn-on' fluorescent sensor for Cd2+ and Zn2+.
C-1H functions as a 'turn-off' fluorescent sensor for Co2+, Ni2+, and Cu2+.
These findings highlight the potential of chiral macrocycles in developing selective metal ion detection systems.