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Molecular Recognition at a Monolayer Interface : 2,4-Diaminopyrimidine—Succinimide Host—Guest Partners

Dawson, Susan L. and Elman, James and Margevich, Douglas E. and McKenna, William and Tirrell, David A. and Ulman, Abraham (1996) Molecular Recognition at a Monolayer Interface : 2,4-Diaminopyrimidine—Succinimide Host—Guest Partners. In: Hydrogels and Biodegradable Polymers for Bioapplications. ACS Symposium Series. No.627. American Chemical Society , Washington, D.C., pp. 187-196. ISBN 9780841234000.

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Molecular recognition at a 2,4-diaminopyrimidine terminated monolayer 1 (host) by a succinimide derivative (guest) has resulted in the formation of bilayers. The bilayers were prepared either from solution or by transfer from the air-water interface to the monolayer substrate. The preorganized 2,4-diaminopyrimidine is oriented for recognition with a molecule of complementary hydrogen bonding ability, succinimide 2. The resultant bilayer 3 is stabilized by the formation of three hydrogen bonds per host-guest pair. We present an example of a self-assembling process, wherein a relatively weak hydrogen bonding interaction (molecular recognition) leads to the formation of bilayers. The bilayer structures and the hydrogen bonding interactions were analyzed by external-reflection Fourier transform infrared spectroscopy (FTIR), ellipsometry, and X-ray photoelectron spectroscopy (XPS).

Item Type:Book Section
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URLURL TypeDescription chapter 15
Tirrell, David A.0000-0003-3175-4596
Additional Information:Copyright © 1996 American Chemical Society. RECEIVED July 6, 1995. Publication Date (Print): May 05, 1996. Publication Date (Print): July 23, 2009. S.L.D. would like to thank Eastman Kodak Company for the opportunity to conduct this work at their facility and acknowledges support from CUMIRP. We thank Professor Howard D. Stidham of the University of Massachusetts for a valuable discussion on pyrimidines, and D. J. Motyl of Eastman Kodak Company for his assistance in obtaining IR spectra.
Funding AgencyGrant Number
Eastman Kodak CompanyUNSPECIFIED
Center for University of Massachusetts-Industry Research on PolymersUNSPECIFIED
Series Name:ACS Symposium Series
Issue or Number:627
Record Number:CaltechAUTHORS:20150209-123523244
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Official Citation:Molecular Recognition at a Monolayer Interface Susan L. Dawson, James Elman, Douglas E. Margevich, William McKenna, David A. Tirrell, and Abraham Ulman Hydrogels and Biodegradable Polymers for Bioapplications. May 5, 1996, 187-196 Doi:10.1021/bk-1996-0627.ch015
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:54560
Deposited By: Anne Hormann
Deposited On:04 Mar 2015 00:34
Last Modified:03 Oct 2019 07:58

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