Formation of the intermediate nitronyl nitroxide-anthracene dyad sensing saccharides.
We design a new saccharides sensor based on the ensemble of compound 2 with a boronic group and compound 3 with two phenolic -OH groups, taking advantage of the fluorescence quenching ability of nitronyl nitroxides and reversible boronate formation between boronic acid and diol. The results show that the fluorescence of compound 2 was largely quenched upon addition of compound 3 due to the formation of the intermediate nitronyl nitroxide-anthracene dyad 1. Sequential addition of saccharides such as fructose to the ensemble of compounds 2 and 3 together with dyad 1 induced the fluorescence enhancement. These results clearly demonstrate the possibility to employ the ensemble of compounds 2 and 3 (with dyad 1) to sense saccharides.
Yu
Yanxin
Y
Beijing National Laboratory for Molecular Sciences, Organic Solids Laboratory, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
Zhang
Deqing
D
Tan
Wei
W
Wang
Zhiyong
Z
Zhu
Daoben
D
D000873:Anthracenes / Q000737:chemistry*; D015374:Biosensing Techniques / Q000379:methods*; D001896:Boron Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000737:chemistry*; D005453:Fluorescence; D006601:Hexoses / Q000032:analysis*; D007093:Imidazoles / Q000737:chemistry*; D009005:Monosaccharides / Q000032:analysis; D009589:Nitrogen Oxides / Q000737:chemistry
C518997:2-(3,4-dihydroxyphenyl)-4,4,5,5-tetramethyl-1-oxylimidazole 3-oxide; C518998:2-(4-(2-(anthracen-10-yloxy)ethoxycarbonyl)phenyl)-2-hydroxy-5-(4,4,5,5-tetramethyl-1-oxylimidazole 3-oxide-2-yl)-1,3,2-benzodioxaborinane; C518996:4-(2-(anthracen-10-yloxy)ethoxycarbonyl)phenylboronic acid; D000873:Anthracenes; D001896:Boron Compounds; D001897:Boronic Acids; D003497:Cyclic N-Oxides; D006601:Hexoses; D007093:Imidazoles; D009005:Monosaccharides; D009589:Nitrogen Oxides; C034020:anthracene; C039900:nitroxyl