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2,6-Diphenylpyridine-based fluorophores: Synthesis, photophysical properties and effects of protonation

Paper ID Volume ID Publish Year Pages File Format Full-Text
26162 43937 2013 7 PDF Available
Title
2,6-Diphenylpyridine-based fluorophores: Synthesis, photophysical properties and effects of protonation
Abstract

A new series of 2,6-diphenylpyridine-based fluorophores with different type of substituents (R = Br, H, OMe, NMe2 and NPh2 for 2–6) were prepared, and their photophysical properties in neutral and protonated state were investigated. With the increasing of the donor ability of substituents in 2–6, their UV/vis and emission spectra show a successive red shift. In addition, a large intramolecular charge transfer (ICT) was observed in 5 and 6, which can be confirmed by time-dependent density functional theory (TD-DFT) calculation, and X-ray crystallographic analysis for 5. All compounds studied in this work show proton-sensitive fluorescence. It was found that 2 and 3 were capable of ratiometric emission signaling of protons, 4 and 6 showed proton-induced quenching in their fluorescence, while 5 revealed a proton-induced ON–OFF–ON switching of its emission.

► A series of 2,6-diphenylpyridine-based fluorophores were prepared. ► Solvent dependent UV/vis and emission spectra was observed. ► TD-DFT calculation and X-ray crystallographic analysis confirmed intramolecular charge transfer. ► All compounds studied in this work show proton-sensitive fluorescence.

Keywords
2,6-Diphenylpyridine; Emission spectrum; Intramolecular charge transfer; Proton-sensitive fluorescence
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2,6-Diphenylpyridine-based fluorophores: Synthesis, photophysical properties and effects of protonation
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 251, 1 January 2013, Pages 106–112
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
100% Money Back Guarantee
Full-text PDF Download
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