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Issue 124, 2015
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Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives

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Abstract

In an attempt to create a flavone derivative able to take part in Excited State Intramolecular Double Proton Transfer (ESIDPT), we synthesized two carbonyl derivatives of 3,7-dihydroxyflavone, both containing two different proton-transfer sites as well as related carbonyl derivatives of 3-hydroxyflavone and 7-hydroxyflavone. All the examined hydroxyflavones were found to participate in the Excited State Intramolecular Proton Transfer (ESIPT). ESIPT which involves 3-hydroxyl and 4-carbonyl groups was found to have a higher barrier compared to ESIPT involving 7-hydroxyl and 6/8-carbonyl fragments. According to the data presented, 3,7-dihydroxy-2-phenyl-6-(3-phenylpropanoyl)-4H-chromen-4-one undergoes a two-stage ESIDPT with formation of an intermediate tautomer. This kind of ESIDPT leads to a tautomeric form with an abnormally low rate of radiative deactivation of the excited state, which conditions low fluorescence quantum yield. The behavior of 3,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde in the electronically excited state is similar to 3-hydroxyflavone derivatives, thus we conclude the occurrence of a single ESIPT in this compound.

Graphical abstract: Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives

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Publication details

The article was received on 15 Jul 2015, accepted on 19 Nov 2015 and first published on 23 Nov 2015


Article type: Paper
DOI: 10.1039/C5RA13912K
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RSC Adv., 2015,5, 102191-102203

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    Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives

    I. E. Serdiuk and A. D. Roshal, RSC Adv., 2015, 5, 102191
    DOI: 10.1039/C5RA13912K

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