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Adaptive maleimide-fused macrocyclic clamps: Synthesis, structures, and complexations with polycyclic aromatic hydrocarbons
Dyes and Pigments ( IF 4.5 ) Pub Date : 2024-04-20 , DOI: 10.1016/j.dyepig.2024.112158
Zi-Jian Jiang , Shan-Yuan Zhong , Yu-Hua Chen , Qing Liao , Mei-Jin Lin

The photoactive macrocyclic molecules attract attention because of their important roles in supramolecular chemistry as well as photoelectronic applications. Herein, two D-A conjugated macrocycles containing two maleimide nodes have been successfully obtained via an one-pot cascade reaction of Perkin and imidization condensations. Owing to the incorporation of two bulky 1,4-dimethoxybenzene moieties at the narrow maleimide corners, the obtained conjugated macrocycles have been equipped with two adaptive clamps, which can adjust to the guest sizes to capture the guest molecules. Interestingly, the co-crystallization with larger-sized polycyclic aromatic hydrocarbons (PAHs) leads to the 1:1 host-guest complexes, while with smaller-sized solvents results in the 1:2 complexes. Furthermore, the rotatable 1,4-dimethoxybenzene moieties endowed such macrocyclic fluorophores with pronounced solvatochromic and aggregation-induced emission enhancement (AIEE) phenomena.

中文翻译:


自适应马来酰亚胺稠合大环钳:合成、结构以及与多环芳烃的络合



光活性大环分子因其在超分子化学和光电应用中的重要作用而引起人们的关注。在此,通过Perkin和酰亚胺化缩合的一锅级联反应成功获得了两个含有两个马来酰亚胺节点的D-A共轭大环化合物。由于在狭窄的马来酰亚胺角处掺入了两个大的1,4-二甲氧基苯部分,所获得的共轭大环配备了两个自适应夹具,可以调整客体尺寸以捕获客体分子。有趣的是,与较大尺寸的多环芳烃 (PAH) 共结晶会形成 1:1 主客体复合物,而与较小尺寸的溶剂共结晶会形成 1:2 复合物。此外,可旋转的1,4-二甲氧基苯部分赋予此类大环荧光团明显的溶剂化显色和聚集诱导发射增强(AIEE)现象。
更新日期:2024-04-20
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