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基于 1,1'-联萘的新型席夫碱大环化合物用于荧光识别。

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

机构信息

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

Department of Green and Sustainable Chemistry, Applied Chemistry, School of Engineering, Tokyo Denki University, 5 Senju-Asahi-cho, Adachi-ku, Tokyo, Japan.

出版信息

Luminescence. 2021 Sep;36(6):1561-1568. doi: 10.1002/bio.4101. Epub 2021 Jun 19.

DOI:10.1002/bio.4101
PMID:34101337
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 Zn or Cd showed a 'turn-on' response accompanied by fluorescence enhancement at 510 nm six times for Cd and 13 times for Zn . In contrast, C-1H revealed a 'turn-off' response upon the addition of Co , Ni , and Cu .

摘要

一种新型手性聚亚胺大环 C-1 通过手性二萘并[2,1-d:1',2'-f][1,3]二氧杂环戊烯衍生物的醛与邻苯二胺通过席夫碱形成自缩合而设计和合成,相应的聚亚胺大环 C-1H 通过聚亚胺大环的还原而获得。紫外可见和荧光光谱研究表明,C-1 和 C-1H 均以 1:2 的比例与金属离子形成配合物。C-1 与 Zn 或 Cd 加合时的荧光行为表现出“开启”响应,伴随 510nm 处荧光增强,Cd 增强六倍,Zn 增强十三倍。相比之下,C-1H 与 Co、Ni 和 Cu 加合时呈现“关闭”响应。

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