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Influence of the spacer on the photoreactivity of flurbiprofen-tyrosine dyads

Paper ID Volume ID Publish Year Pages File Format Full-Text
26188 43938 2016 7 PDF Available
Title
Influence of the spacer on the photoreactivity of flurbiprofen-tyrosine dyads
Abstract

•Photobehaviour dependence on interchromophoric distance.•Stereoselective dynamic fluorescence quenching.•Intramolecular Electron transfer and exciplex formation.

The photoreactivity of diastereomeric dyads containing (S)- or (R)-flurbiprofen (FBP) and (S)-Tyr, either directly linked (1) or separated by a cyclic spacer (3) has been investigated. The main feature is a remarkable intramolecular quenching of FBP fluorescence, especially in 1. The process is clearly configuration dependent, being more efficient for the (R,S)- diastereomer in 1 and for the (S,S)- analogue in 3. Noteworthy, exciplex emission is detected in the 380–500 nm region in the case of 3. Fluorescence decay kinetics from the femtosecond to the nanosecond time-domains provides evidence for the dynamic nature of the quenching. In agreement with the steady-state and time-resolved observations, molecular modelling points to a more favourable geometric arrangement of the two interacting chromophores in 1 than in 3.

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Keywords
Exciplex; Fluorescence quenching; Fluorescence upconversion; Laser flash photolysis; Time-correlated single photon counting
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Influence of the spacer on the photoreactivity of flurbiprofen-tyrosine dyads
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volumes 322–323, 15 May–1 June 2016, Pages 95–101
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
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Price was $35.95
You save - $31
Price after discount Only $4.95
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