Self-assembly of a "double dynamic covalent" amphiphile featuring a glucose-responsive imine bond.
Glucose binding via boronate ester linkages selectively triggers imine bond formation between 4-formylphenylboronic acid and octylamine, leading to the formation of vesicular aggregates in aqueous solutions. This "double dynamic covalent assembly" allows the facile selective sensing of glucose against the otherwise serious interferant fructose, without the need to resort to synthetic effort.
Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Xiamen University, Xiamen 361005, China. ybjiang@xmu.edu.cn and Chemistry, University of Southampton, Southampton SO17 1BJ, UK.
Xin
X
Wu
Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Xiamen University, Xiamen 361005, China. ybjiang@xmu.edu.cn.
Xuan-Xuan
XX
Chen
Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Xiamen University, Xiamen 361005, China. ybjiang@xmu.edu.cn.
Miao
M
Zhang
Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Xiamen University, Xiamen 361005, China. ybjiang@xmu.edu.cn.
Zhao
Z
Li
Chemistry, University of Southampton, Southampton SO17 1BJ, UK.
Philip A
PA
Gale
Department of Chemistry, College of Chemistry and Chemical Engineering, The MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Xiamen University, Xiamen 361005, China. ybjiang@xmu.edu.cn.
Yun-Bao
YB
Jiang
D000588:Amines / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D046911:Macromolecular Substances / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D010078:Oxazines / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D013501:Surface-Active Agents / Q000737:chemistry*
C000611982:4-formylphenylboronic acid; D000588:Amines; D001547:Benzaldehydes; D001897:Boronic Acids; D005456:Fluorescent Dyes; D007097:Imines; D046911:Macromolecular Substances; D010078:Oxazines; D013501:Surface-Active Agents; D005947:Glucose; C044808:nile red; C008699:octylamine; D005690:Galactose