Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

Wang, YY (Wang, Yu-Ying)^{[ 1 ]} ; Kong, Y (Kong, Yong)^{[ 2 ]} ; Zheng, Z (Zheng, Zhe)^{[ 1 ]} ; Geng, WC (Geng, Wen-Chao)^{[ 1 ]} ; Zhao, ZY (Zhao, Zi-Yi)^{[ 1 ]} ; Sun, HW (Sun, Hongwei)^{[ 1 ]} ; Guo, DS (Guo, Dong-Sheng)^{[ 1 ]}

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15: 1394-1406

DOI: 10.3762/bjoc.15.139

摘要

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-(p-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.