Wang Yu-Ying, Kong Yong, Zheng Zhe, Geng Wen-Chao, Zhao Zi-Yi, Sun Hongwei, Guo Dong-Sheng
College of Chemistry, Key Laboratory of Functional Polymer Materials, State Key Laboratory of Elemento-Organic Chemistry, Tianjin Key Laboratory of Biosensing and Molecular Recognition, Nankai University, Tianjin 300071, P. R. China.
Research Institute of Petroleum Engineering, Sinopec, Beijing 100101, P. R. China.
Beilstein J Org Chem. 2019 Jun 25;15:1394-1406. doi: 10.3762/bjoc.15.139. eCollection 2019.
We herein describe the comprehensive investigation of the complexation behavior of a guanidinium-modified calix[5]arene pentaisohexyl ether (GC5A) with a variety of typical luminescent dyes. Fluorescein, eosin Y, rose bengal, tetraphenylporphine sulfonate and sulfonated aluminum phthalocyanine were employed as classical aggregation-induced quenching dyes. 2-(-Toluidinyl)naphthalene-6-sulfonic acid and 1-anilinonaphthalene-8-sulfonic acid were selected as representatives of intramolecular charge-transfer dyes. Phosphated tetraphenylethylene was involved as the classical aggregation-induced emission dye. Sulfonated acedan representing one example of two-photon fluorescent probes, was also investigated. A ruthenium(II) complex with carboxylated bipyridyl ligands was included as a representative candidate of luminescent transition-metal complexes. We determined the association constants of the GC5A-dye complexes by fluorescence titration and discuss the complexation-induced photophysical changes. In addition, a comparison of the complexation behavior of GC5A with that of other macrocycles and potential applications according to the diverse photophysical responses are provided.
我们在此描述了胍基修饰的杯[5]芳烃五异己基醚（GC5A）与多种典型发光染料的络合行为的全面研究。荧光素、曙红Y、孟加拉玫瑰红、四苯基卟啉磺酸盐和磺化铝酞菁被用作经典的聚集诱导猝灭染料。2-（-甲苯氨基）萘-6-磺酸和1-苯胺基萘-8-磺酸被选作分子内电荷转移染料的代表。磷酸化四苯乙烯作为经典的聚集诱导发光染料参与其中。磺化吖啶作为双光子荧光探针的一个例子也被研究。一种带有羧基化联吡啶配体的钌（II）配合物作为发光过渡金属配合物的代表性候选物被纳入研究。我们通过荧光滴定法测定了GC5A-染料配合物的缔合常数，并讨论了络合诱导的光物理变化。此外，还比较了GC5A与其他大环化合物的络合行为，并根据不同的光物理响应探讨了其潜在应用。
