ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Investigations of the Photo-Fading of Tautomeric Azo Dyes. VI. The Photochemical Oxidation by Singlet Oxygen of Phenylazoacetylacetones and PhenylazopyrazolonesThe dye-sensitized photo-oxidation by singlet oxygen of phenylazoacetylacetones (1) and Phenylazopyrazolones (2) has been investigated. The photo-fading of dyes is accelerated in the presence of Methylene Blue, a sensitizer of singlet oxygen, in airsatured methanolAn excellent relationship exists between the fading-rate of a series of dyes (1) and Hammett-σ-constants. An unexpected trend was found for photo-fading of a series of dyes (2). The Hammett plot consists of two parts, with a negative slope derived from electron-releasing substituents and a positive slope derived from electron-withdrawing substituents. The anomalous photo-fading is due to an attack of singlet oxygen on the more reactive anion of the phenylazopyrazolones in the case of electron-withdrawing substituents. In methanol containing acetic acid the dyes (2) exist only as the hydrazone tautomers. Under these conditions the fading-rate show a linear relationship with σ-constants.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19843260617