Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives
Illia Serdiuk , A. D. Roshal
AbstractIn 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.
|Journal series||RSC Advances, ISSN 2046-2069, (A 30 pkt)|
|Publication size in sheets||0.6|
|License||Journal (articles only); published final; ; with publication|
|Score|| = 35.0, ArticleFromJournal|
= 35.0, ArticleFromJournal
|Publication indicators||: 2015 = 3.289 (2) - 2015=3.485 (5)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.