Monosaccharide Detection with 4,7-Phenanthrolinium Salts:  Charge-Induced Fluorescence Sensing

Abstract

Herein we report the preparation of novel boronic acid-substituted 4,7-phenanthrolinium viologens and demonstrate their ability to quench the fluorescence of 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (pyranine). In an aqueous buffer solution at pH 7.4, the quenching is suppressed upon binding to monosaccharides, as was determined by Stern-Volmer analysis. Thus, the combination of the viologen and pyranine is shown to act as a saccharide sensor. A spectroscopic study reveals a ground-state complexation between the viologens and pyranine. In the presence of monosaccharide, the complex dissociates, resulting in a relative increase in the fluorescence. In comparison to the dipyridyl-derived viologen, the phenanthrolinederived viologen shows a greater fluorescence quenching as well as sensitivity to and an unusual selectivity for glucose.

Synthesis, Evaluation, and Computational Studies of Naphthalimide‐Based Long‐Wavelength Fluorescent Boronic Acid Reporters

“…[7,9,15,[31][32][33][34][35] Among those compounds, a boron-dipyrromethane (BODIPY) dye functionalized with a phenylboronic acid group (510 nm) was the only watersoluble fluorescent probe that showed fluorescence intensity increases upon sugar binding. [36] Long-wavelength emission has been observed with the 1,8-naphthalimide fluorophore, and the addition of a 4-amino group to this compound has been shown to significantly change its fluorescence properties.…”

Chiral Binol–Bisboronic Acid as Fluorescence Sensor for Sugar Acids

“…[1] Unsurprisingly the ability to derive synthetic receptors with the capacity to selectively detect specific saccharides (and related molecules) and signal their presence by altering the optical signature has captured the attention of supramolecular chemists. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] Binol is an important chiral building block and has been widely used in asymmetric catalysis, [17,18] and for enantioselective fluorescence sensors bearing a variety of recognition elements. [19][20][21][22][23][24][25][26][27][28][29][30] In early work, a binol-based bisboronic acid (1) was used to recognize the enantiomers of monosaccharides, such as d/l-glucose, -fructose, and -galactose.…”

N-[2-(Hydroxymethoxyboryl)benzyl]-4,7-phenanthrolinium bromide methanol solvate

“…The compound N-[2-(hydroxymethoxyboryl)benzyl]-4,7phenanthrolinium bromide methanol solvate, (I), is of interest as a saccharide sensor because the¯uorescence quenching of a pyranine±(I) complex is suppressed in the presence of monosaccharides (Camara et al, 2002;Suri et al, 2003). Another compound in this study, N,N H -bisbenzyl-4,7-phenanthrolinium dibromide methanol solvate, containing a dication, was reported in the previous paper (Olmstead et al, 2004).…”