Benzoid-Quinoid Tautomerism of Schiff Bases and Their Structural Analogs: LII.* Schiff Bases Derived from 6-tert-Butyl-5-hydroxy- and 5-Hydroxy-6-iodo-2,3-tetra-methylenebenzo[b]furan-4-carbaldehydes View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2002-09

AUTHORS

V. P. Rybalkin, A. D. Dubonosov, E. N. Shepelenko, L. L. Popova, N. I. Makarova, A. V. Tsukanov, V. A. Bren', V. I. Minkin

ABSTRACT

Two series of Schiff bases, 4-aryl(alkyl)iminomethyl-6-tert-butyl-5-hydroxy- and 4-aryl(alkyl)iminomethyl-5-hydroxy-6-iodo-2,3-tetramethylenebenzo[b]furans were synthesized. These compounds in solution give rise to tautomeric benzoid-quinoid equilibrium; the fraction of the quinoid form in the equilibrium mixture increases with rise in solvent polarity and in going from N-aryl to N-alkyl derivatives. The benzoid tautomer shows fluorescence with an anomalous Stokes shift. The absorption and luminescence spectral properties of the examined Schiff bases make them promising as signal fragments of chemosensors for metal cations. More... »

PAGES

1326-1330

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1021607930539

DOI

http://dx.doi.org/10.1023/a:1021607930539

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1034957212


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