Boronic acid library for selective, reversible near-infrared fluorescence quenching of surfactant suspended single-walled carbon nanotubes in response to glucose

Kyungsuk Yum, Jin Ho Ahn, Thomas P. McNicholas, Paul W. Barone, Bin Mu, Jong Ho Kim, Rishabh M. Jain, Michael S. Strano

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

Figure Persented: 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.

Original languageEnglish (US)
Pages (from-to)819-830
Number of pages12
JournalACS Nano
Volume6
Issue number1
DOIs
StatePublished - Jan 24 2012
Externally publishedYes

Fingerprint

Boronic Acids
Single-walled carbon nanotubes (SWCN)
glucose
Surface-Active Agents
Glucose
Quenching
Surface active agents
Fluorescence
carbon nanotubes
quenching
surfactants
Infrared radiation
fluorescence
acids
Acids
Screening
screening
Sodium Cholate
Electrons
Excited states

Keywords

  • boronic acids
  • glucose
  • near-infrared fluorescence
  • near-infrared optical sensor
  • single-walled carbon nanotubes

ASJC Scopus subject areas

  • Engineering(all)
  • Materials Science(all)
  • Physics and Astronomy(all)

Cite this

Boronic acid library for selective, reversible near-infrared fluorescence quenching of surfactant suspended single-walled carbon nanotubes in response to glucose. / Yum, Kyungsuk; Ahn, Jin Ho; McNicholas, Thomas P.; Barone, Paul W.; Mu, Bin; Kim, Jong Ho; Jain, Rishabh M.; Strano, Michael S.

In: ACS Nano, Vol. 6, No. 1, 24.01.2012, p. 819-830.

Research output: Contribution to journalArticle

Yum, Kyungsuk ; Ahn, Jin Ho ; McNicholas, Thomas P. ; Barone, Paul W. ; Mu, Bin ; Kim, Jong Ho ; Jain, Rishabh M. ; Strano, Michael S. / Boronic acid library for selective, reversible near-infrared fluorescence quenching of surfactant suspended single-walled carbon nanotubes in response to glucose. In: ACS Nano. 2012 ; Vol. 6, No. 1. pp. 819-830.
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AU - Barone, Paul W.

AU - Mu, Bin

AU - Kim, Jong Ho

AU - Jain, Rishabh M.

AU - Strano, Michael S.

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N2 - Figure Persented: 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.

AB - Figure Persented: 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.

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