Journal
JOURNAL OF FLUORESCENCE
Volume 12, Issue 2, Pages 147-154Publisher
KLUWER ACADEMIC/PLENUM PUBL
DOI: 10.1023/A:1016884011396
Keywords
boronic acids; glucose sensing; N-phenyl-1,8-naphthalimide; fluorescence sensing
Funding
- NCRR NIH HHS [P41 RR008119] Funding Source: Medline
- NIGMS NIH HHS [R15 GM057855] Funding Source: Medline
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Spectroscopic and photophysical properties of two fluorescent probes for monosaccharides are presented. Probes are based on the N-phenyl-1,8-naphthalimide structure having the boronic acid group [R-B(OH)(2)] in ortho in one case, and meta in the other case, positions of the N-phenyl group. Formation of the anionic form of the boronic acid group [R-B(OH)(3)(-)] induced a substantial decrease of the steady-state fluorescence of both compounds. Because no change in the fluorescence lifetime from the neutral to the anionic forms is observed, static quenching resulting from photoinduced electron transfer from the anionic form of the boronic acid is used to explain the decrease of the emission intensity. Both compounds show substantial decreases of their fluorescence intensity in the presence of sugars. In addition, this decrease of the fluorescence intensity is associated with an increase of the fluorescence lifetime for the ortho derivative while no effect on the lifetime is observed for the meta derivative. Both photoinduced electron transfer and steric hindrance are discussed to correlate the observed results.
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