Tautomeric forms of PPI dendrimers functionalized with 4-(4′-ethoxybenzoyloxy)salicylaldehyde chromophores

[Display omitted] ► SA chromophore groups are formed by bonding terminal groups to PPI dendrimers. ► SA chromophore groups reveal four most stable tautomeric forms. ► Tautomeric properties of SA groups depend on the dendrimer generation and solvent. ► Aggregation of SA chromophores facilitates forma...

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Bibliographic Details
Published in:Chemical physics 2012-08, Vol.404, p.2-8
Main Authors: Franckevičius, M., Vaišnoras, R., Marcos, M., Serrano, J.L., Gruodis, A., Galikova, N., Gulbinas, V.
Format: Article
Language:English
Subjects:
Chromophore groups
Keto-enol tautomerism
PPI dendrimers
Schiff base
trans–cis isomerism
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Summary:[Display omitted] ► SA chromophore groups are formed by bonding terminal groups to PPI dendrimers. ► SA chromophore groups reveal four most stable tautomeric forms. ► Tautomeric properties of SA groups depend on the dendrimer generation and solvent. ► Aggregation of SA chromophores facilitates formation of the trans-keto tautomers. ► Fluorescence of PPI SA dendrimers is attributed to nπ∗ states of keto tautomers. Bonding of the promesogenic unit derived from 4-(4′-ethoxybenzoyloxy)salicylaldehyde to the amino terminated PPI dendrimer chains results in formation of the salicylidenimine chromophore groups. Absorption and fluorescence investigations of the dendrimer solutions supported by the quantum chemistry calculations revealed that the chromophore groups may exist in enol and keto tautomeric forms with relative concentrations depending on the dendrimer generation and solvent. The dendrimer fluorescence is attributed to nπ∗ states of keto tautomers which may also be formed from excited enol tautomers.
ISSN:0301-0104
DOI:10.1016/j.chemphys.2011.12.017