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

Illia Serdiuk , A. D. Roshal

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.
Author Illia Serdiuk (FCh / DPCh / PK)
Illia Serdiuk,,
- Pracownia Krystalochemii
, A. D. Roshal
A. D. Roshal,,
-
Journal seriesRSC Advances, ISSN 2046-2069, (A 30 pkt)
Issue year2015
Vol5
No124
Pages102191-102203
Publication size in sheets0.6
DOIDOI:10.1039/c5ra13912k
URL http://pubs.rsc.org/en/content/articlepdf/2015/ra/c5ra13912k
Languageen angielski
LicenseJournal (articles only); published final; Uznanie Autorstwa - Użycie Niekomercyjne (CC-BY-NC); with publication
Score (nominal)35
ScoreMinisterial score = 35.0, 20-12-2017, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 20-12-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2015 = 3.289 (2) - 2015=3.485 (5)
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