title: Boronic acid library for selective, reversible near-infrared fluorescence quenching of surfactant suspended single-walled carbon nanotubes in response to glucose.
abstract: We describe the high-throughput screening of a library of 30 boronic acid derivatives to form complexes with sodium cholate suspended single-walled carbon nanotubes (SWNTs) to screen for their ability to reversibly report glucose binding via a change in SWNT fluorescence. The screening identifies 4-cyanophenylboronic acid which uniquely causes a reversible wavelength red shift in SWNT emission. The results also identify 4-chlorophenylboronic acid which demonstrates a turn-on fluorescence response when complexed with SWNTs upon glucose binding in the physiological range of glucose concentration. The mechanism of fluorescence modulation in both of these cases is revealed to be a photoinduced excited-state electron transfer that can be disrupted by boronate ion formation upon glucose binding. The results allow for the elucidation of design rules for such sensors, as we find that glucose recognition and transduction is enabled by para-substituted, electron-withdrawing phenyl boronic acids that are sufficiently hydrophobic to adsorb to the nanotube surface.
authors: Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors: Kyungsuk
authors: K
authors: Yum
authors: Jin-Ho
authors: JH
authors: Ahn
authors: Thomas P
authors: TP
authors: McNicholas
authors: Paul W
authors: PW
authors: Barone
authors: Bin
authors: B
authors: Mu
authors: Jong-Ho
authors: JH
authors: Kim
authors: Rishabh M
authors: RM
authors: Jain
authors: Michael S
authors: MS
authors: Strano
mesh_terms: D015374:Biosensing Techniques / Q000295:instrumentation; D001897:Boronic Acids / Q000737:chemistry*; D003460:Crystallization / Q000379:methods*; D004867:Equipment Design; D019544:Equipment Failure Analysis; D005947:Glucose / Q000032:analysis* / Q000737:chemistry; D037742:Nanotubes, Carbon / Q000737:chemistry* / Q000648:ultrastructure; D010316:Particle Size; D013050:Spectrometry, Fluorescence / Q000295:instrumentation*; D019265:Spectroscopy, Near-Infrared / Q000295:instrumentation*; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D037742:Nanotubes, Carbon; D013501:Surface-Active Agents; D005947:Glucose