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Excited state intramolecular charge transfer suppressed proton transfer process in 4-(diethylamino)-2-hydroxybenzaldehyde
S JANA, S DALAPATI,
Published in AMER CHEMICAL SOC
2013
PMID: 23642189
Volume: 117
   
Issue: 21
Pages: 4367 - 4376
Abstract
In this work, we report intramolecular charge transfer (ICT) suppressed excited state intramolecular proton transfer (ESIPT) process in 4-(diethylamino)-2-hydroxybenzaldehyde (DEAHB). Photophysical properties of DEAHB have been extensively studied in different solvents with varying pH, polarity, and hydrogen bonding capability of the solvent using steady state and time-resolved spectroscopy. To establish the competition between the ICT and ESIPT processes in DEAHB, we have synthesized and studied the photophysical properties of 4-(diethylamino)-2-methoxybenzaldehyde (DEAMB) molecule where only the charge transfer process has been observed. Recently, we have reported simple Schiff base molecules (J. Phys. Chem. A 2012, 116, 10948) formed by condensation of DEAHB and hydrazine (5-(diethylamino)-2-[(4-(diethylamino) benzylidene)hydrazonomethyl]phenol (DDBHP) and N,N′-bis(4-N,N- (diethylamino)salisalidene)hydrazine (DEASH)), where charge transfer is assisted by the proton transfer process. In the present case, the DEAHB molecule shows the reverse phenomenon; i.e., charge transfer is suppressed by the proton transfer process. Comparing the photophysical properties of DEAHB with DEAMB it is also found that ICT process in DEAHB is suppressed by the ESIPT process. © 2013 American Chemical Society.
About the journal
JournalJournal of Physical Chemistry A
PublisherAMER CHEMICAL SOC
ISSN1089-5639
Open AccessNo