Abstract
Reactivity of gaseous 1-arylazo-2-naphthol dyes and their complexes with cellulose, after adsorption on cellulose, towards singlet molecular oxygen, 1O 2, are investigated based on frontier molecular orbital theory. Results reveal that electrophilic reactions may occur predominately for the studied species, with the oxidizing agent 1O 2 as electrophile. The − SO 3 − functionalized 1-arylazo-2-naphtol tautomers (soft nucleophiles) and their complexes with the cellulose are shown to be less reactive towards 1O 2 and under thermodynamic control; while the − SO 3 H functionalized 1-arylazo-2-naphtol tautomers (hard nucleuphiles) and their cellulose complexes are fairly reactive and under kinetic control. According to the frontier molecular orbital theory, the sites more vulnerable for 1O 2 attack (the atomic positions and double bounds) are similar for both azo dyes and their complexes with cellulose. Thermodynamic study reveals that the photo-oxidation reactions are exothermic and spontaneous, except for cycloaddition of hydrazone tautomers. TD-DFT calculations confirm the decolorization and color fading phenomenon during the photo-decomposition reaction.
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