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

Susan L. Dawson, James Elman, Douglas E. Margevich, William McKenna, David A. Tirrell, Abraham Ulman

Research output: Contribution to journalArticle

Abstract

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).

Original languageEnglish (US)
Pages (from-to)187-196
Number of pages10
JournalACS Symposium Series
Volume627
StatePublished - 1996

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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