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Excited state proton transfer assisted fluorescence resonance energy transfer in an inclusion complex of a β-CD derivative

Paper ID Volume ID Publish Year Pages File Format Full-Text
28162 44062 2012 6 PDF Available
Title
Excited state proton transfer assisted fluorescence resonance energy transfer in an inclusion complex of a β-CD derivative
Abstract

The inclusion complex of Rhodamin B (Rh B) with (N-6-deoxy-β-cyclodextrin-6-yl-1-aminocarbonyl)-3-(4-fluorobenzoyl)-7-pyridin-4-yl indolizine [designated as compound (1)] is shown to be a potential pH sensor based on fluorescence resonance energy transfer (FRET). By steady state and time-resolved fluorimetry it has been established that (i) an excited state proton transfer (ESPT) occurs between the two prototropic forms, (1·H+) and (1·H2+2) of (1), (ii) a FRET occurs in the inclusion complex whereby energy is transferred to Rh B and (iii) (1·H2+2)* is much more efficient than (1·H+)* in the FRET. Hence this FRET is ESPT-assisted. Donor–acceptor distance from the FRET result shows that the (4-fluorobenzoyl)-7-pyridin-4-yl indolizine cap of (1) opens up in the (1·H2+2) form.

Graphical abstractPhotograph displays fluorescence under exposure to UV lamp (356 nm). ESPT is demonstrated by (A) aqueous solution of compound (1) at pH 4.5 and (B) same solution at pH 2.0. ESPT-assisted FRET is demonstrated by (C) mixture of compound (1) and Rh B at pH 4.5, (D) same solution at pH 2.0.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Excited state proton transfer assisted FRET is observed with the inclusion complex of (N-6-deoxy-β-cyclodextrin-6-yl-1-aminocarbonyl)-3-(4-fluorobenzoyl)-7-pyrridin-4-yl indolizine, (1), with Rh B in the pH range 4.5–2.0. ► FRET to Rh B in the complex occurs much more efficiently from the diprotonated form than the monoprotonated form of (1). ► Compound (1) is a potential FRET based pH sensor. ► The fluorophore cap of the β-CD derivative opens up during protonation.

Keywords
ESPT; FRET; Inclusion complex; pH sensor
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Excited state proton transfer assisted fluorescence resonance energy transfer in an inclusion complex of a β-CD derivative
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 238, 15 June 2012, Pages 29–34
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
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