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

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A novel Schiff base macrocycle based on 1,1′-binaphthyl for fluorescence recognition
Luminescence ( IF 3.2 ) Pub Date : 2021-06-08 , DOI: 10.1002/bio.4101
Hiroki Tokunaga ₁ , Kotoha Kazama ₂ , Masaki Tsuboi ₁ , Makoto Miyasaka _{1,

2,

3}

Affiliation

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⁺.

中文翻译：

基于1,1'-联萘的新型席夫碱大环用于荧光识别

通过手性二萘并[ 2,1-d:1',2'-f ][1,3]二氧杂环庚烷衍生物与邻苯二胺的二醛自缩合设计合成了一种新型手性聚亚胺大环C-1通过席夫碱的形成，通过聚亚胺大环的还原得到相应的聚胺大环C-1H。UV-vis 和荧光光谱研究表明C-1和C-1H与金属离子以 1:2 的比例形成络合物。加入Zn ²⁺或Cd ²⁺后C-1的荧光行为显示了“开启”响应，伴随着 510 nm 处的荧光增强，Cd ²⁺为 6倍，Zn ²⁺为 13 倍。相比之下，C-1H在添加 Co ²⁺、Ni ²⁺和 Cu ^{2+ 后}显示出“关闭”响应。

更新日期：2021-06-08

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