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Photoreactions of n-alkyl-3-nitrophenyl ethers with aromatic amines in SDS micelles: A laser flash photolysis study

Paper ID Volume ID Publish Year Pages File Format Full-Text
27358 44018 2011 6 PDF Available
Title
Photoreactions of n-alkyl-3-nitrophenyl ethers with aromatic amines in SDS micelles: A laser flash photolysis study
Abstract

The quenching of the triplet state of three n-alkyl 3-nitrophenyl ethers: 3-nitroanisol (3-NA), n-butyl 3-nitrophenyl ether (3-NB) and n-decyl 3-nitrophenyl ether (3-ND) by four aniline derivatives: aniline (AN), N,N-dimethylaniline (DMA), 2,4,6-trimethylaniline (TMA), and 4-tetradecylaniline (TDA), was investigated in aqueous micellar SDS solutions by laser flash photolysis. The transient absorption spectra for 3-NA and 3-NB reveal the formation of long-lived intermediate species in the presence of all four quenchers, while for 3-ND no amine-induced intermediates are observed. Comparison of the transient absorption spectra of the probe 3-NA in the presence of DMA in aqueous and micellar solutions shows that the intermediate species are favored by the SDS micelles. With DMA and TMA as quenchers the intermediates are suggested to be the ion radicals generated by single electron transfer from the amine to the probe in the triplet excited state. For the quenchers AN and TDA, the intermediates may be σ-complexes. The relative quenching efficiencies generally decrease as the affinity of the quencher for the micellar phase (AN < DMA < TMA < TDA) increases and the mobility of the excited probe (3-NA > 2-NB) decreases.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Photoreactions of nitrophenyl ethers with anilines are studied in micellar SDS. ► Transient spectra show formation via electron transfer of long-lived intermediates. ► Nature of the intermediates is determined by amine and nitrophenyl ether structures.

Keywords
Photosubstitution reactions; Amines; Meisenheimer complex; Triplet state; n-Alkyl 3-nitrophenyl ether
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Photoreactions of n-alkyl-3-nitrophenyl ethers with aromatic amines in SDS micelles: A laser flash photolysis study
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 222, Issue 1, 5 July 2011, Pages 34–39
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
Full-text PDF Download
Online Support
Any Questions? feel free to contact us