Optically induced azo-hydrazone tautomerism of some 2,6-dialkylphenol-based azobenzenes

Elga Markava; Daina Gustina; Inta Muzikante

doi:10.1117/12.425487

10 April 2001 Optically induced azo-hydrazone tautomerism of some 2,6-dialkylphenol-based azobenzenes

Elga Markava, Daina Gustina, Inta Muzikante

Proceedings Volume 4415, Optical Organic and Inorganic Materials; (2001) https://doi.org/10.1117/12.425487
Event: Advanced Optical Materials and Devices, 2000, Vilnius, United States

Abstract

The present publication is devoted to the studies of the azo- hydrazone tautomerism of some 3,5-dialkyl substituted azobenzenes. Four new 3,5-dialkyl-4-hydroxy azobenzenes containing electron acceptor SO₂ groups were synthesized and investigated in solutions, vacuum evaporated (VE) films and doped polymer films. We have observed that azo-hydrazone tautomeric equilibrium depends on the structure of the molecule and the polarity of the solvent. VE films of compounds containing a primary sulfonamide group SOP₂NH₂ exhibit predominating azo form absorption band at about 365 nm, which decreases or disappears on UV irradiation giving rise to characteristic hydrazone absorption band at 430 nm. For the thin VE films of related derivatives containing a secondary sulfonamide group SO₂NHC₄H₉ we have observed predominating hydrazone form absorption band at about 430 nm or a broad band at 380 - 430 nm suggesting a tautomeric mixture. Reversible trans-cis isomerization of 3,5-dimethyl-4- hydroxy azobenzenes containing secondary sulfonamide group in the doped PMMA film was investigated.

Citation Download Citation

Elga Markava, Daina Gustina, and Inta Muzikante "Optically induced azo-hydrazone tautomerism of some 2,6-dialkylphenol-based azobenzenes", Proc. SPIE 4415, Optical Organic and Inorganic Materials, (10 April 2001); https://doi.org/10.1117/12.425487

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