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Synthesis, structural characterization, antibiotics sensing and coordination chemistry of a fluorescent 4-amino-1,8-naphthalimide Tröger’s base supramolecular scaffold
Supramolecular Chemistry ( IF 3.3 ) Pub Date : 2021-03-30 , DOI: 10.1080/10610278.2021.1889551
June I. Lovitt 1, 2 , Deivasigamani Umadevi 1 , Pandi Raja Lakshmi 3 , Brendan Twamley 1 , Thorfinnur Gunnlaugsson 1, 2, 4 , Sankarasekaran Shanmugaraju 3
Affiliation  

ABSTRACT

The solvothermal synthesis and structural characterization of two new supramolecular coordination polymers featuring a unique V-shaped ligand bis-[N-(3-pyridyl)methyl)]-9,18-methano-1,8-naphthalimide-[b,f][1,5]diazocine (TBNap), are reported. The ligand TBNap was synthesized as a racemic mixture and the molecular structure was analyzed crystallographically. TBNap showed a positive solvatochromism effect which was further supported by DFT calculations illustrating the D-π-A type fluorophore effects within the ligand structures. TBNap was further employed as a potential fluorescence probe for the discriminative sensing of structurally assorted antibiotics. A strong fluorescence quenching and preferential binding affinity were realized for nitro-containing antibiotics, i.e., Furazolidone, Nitrofurantoin and Nitrofurazone. The solvothermal reaction of TBNap with Cd(OAc)2‧2H2O afforded a one-dimensional coordination polymer (TB-CP-1, poly-[Cd(TBNap)(OAc)2]). Similarly, reaction between TBNap and CdCl2.4H2O in DMF-C2H5OH rendered a 4,4’-2D coordination sheet (TB-CP-2, poly-[CdCl2(TBNap)]·DMF). The extended polymeric structures are further propagated into 3D supramolecular network through multiple face-to-face π-π interaction.



中文翻译:

荧光4-氨基-1,8-萘二甲酰亚胺特罗格基础超分子支架的合成,结构表征,抗生素传感和配位化学

摘要

两种具有独特V型配体双-[ N-(3-吡啶基)甲基)]-9,18-甲醇-1,8-萘二甲酰亚胺-[ b,f ]的新型超分子配位聚合物的溶剂热合成和结构表征据报道[1,5]重氮电影TBNap)。配体TBNap合成为外消旋混合物,并通过晶体学分析分子结构。TBNap显示出正的溶剂变色效应,这由DFT计算进一步支持,该计算说明了配体结构内的D-π-A型荧光团效应。TBNap进一步被用作潜在的荧光探针,以判别结构上不同的抗生素。对于含硝基的抗生素,即呋喃唑酮,硝基呋喃妥因和硝基呋喃酮,实现了强大的荧光猝灭和优先的结合亲和力。TBNap与Cd(OAc)2·2H2O的溶剂热反应得到一维配位聚合物(TB-CP-1,-[Cd(TBNap)(OAc)2])。同样,在DMF-C2H5OH中TBNap和CdCl2.4H2O之间的反应产生了4,4'-2D配位片(TB-CP-2,-[CdCl2(TBNap)]·DMF)。扩展的聚合物结构通过多个面对面的π-π相互作用进一步传播到3D超分子网络中。

更新日期:2021-04-29
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