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Biphasic Tautomerization Dynamics of Excited 7-Hydroxyquinoline in Reverse Micelles

Kwon, Oh-Hoon and Kim, Taeg Gyum and Lee, Young-Shin and Jang, Du-Jeon (2006) Biphasic Tautomerization Dynamics of Excited 7-Hydroxyquinoline in Reverse Micelles. Journal of Physical Chemistry B, 110 (24). pp. 11997-12004. ISSN 1520-6106. https://resolver.caltech.edu/CaltechAUTHORS:20170419-084724711

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Abstract

The excited-state tautomerization dynamics of 7-hydroxyquinoline in the water pools of reverse micelles has been investigated by monitoring time-resolved fluorescence spectra and kinetics as well as static absorption and emission spectra with a variation of water content and isotopic fractionation. The normal and the tautomeric species are found to reside preferentially in the bound- and the free-water regions of the micelles, respectively. The excited-state tautomerization of the normal species in the bound-water layers is suggested to occur via two different channels, depending on rotamers at the moment of excitation. The cis tautomerizes via proton relay from the enol group to the imino group along a hydrogen-bonded water bridge, unusual in water but common in alcohols, whereas the trans tautomerizes via the stepwise individual acid−base reactions of two prototropic groups as found in bulk water. Proton relay can take place because water in the pools has substantially reduced polarity and disrupted hydrogen-bond networks compared with bulk water.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jp0573184DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jp0573184PublisherArticle
ORCID:
AuthorORCID
Kwon, Oh-Hoon0000-0001-7114-8617
Additional Information:© 2006 American Chemical Society. Received: December 15, 2005; In Final Form: February 24, 2006. Publication Date (Web): May 25, 2006. The authors thank The Korea Research Foundation for Grant KRF-2004-015-C00230. Y.S.L. acknowledges the fellowship of the BK21 Program.
Funders:
Funding AgencyGrant Number
National Research Foundation of KoreaKRF-2004-015-C00230
BK21 ProgramUNSPECIFIED
Issue or Number:24
Record Number:CaltechAUTHORS:20170419-084724711
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170419-084724711
Official Citation:Biphasic Tautomerization Dynamics of Excited 7-Hydroxyquinoline in Reverse Micelles Oh-Hoon Kwon, Taeg Gyum Kim, Young-Shin Lee, and Du-Jeon Jang The Journal of Physical Chemistry B 2006 110 (24), 11997-12004 DOI: 10.1021/jp0573184
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76658
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:19 Apr 2017 16:48
Last Modified:09 Mar 2020 13:18

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