A highly stable quadruply hydrogen-bonded heterocomplex useful for supramolecular polymer blends

Taiho Park, Steven C. Zimmerman, Shoji Nakashima

Research output: Contribution to journalArticlepeer-review

217 Scopus citations

Abstract

The butyl urea of guanosine (UG) presents an ADDA hydrogen-bonding array that is complementary to the DAAD array of 2,7-diamido-1,8-naphthyridine (DAN). The stability of the DAN·UG complex was measured by fluorimetry using the fluorescence resonance energy transfer (FRET) from the naphthyridine ring to a coumarin 343 moiety linked covalently to the UG unit. The quadruply hydrogen-bonded complex is extremely stable with a measured association constant, Kassoc, of 3 × 108 M-1. Unlike related hydrogen-bonding modules, the guanosine urea, UG, contains a relatively fixed tautomeric form and only weakly self-associates (Kdimer = ca. 200 M-1). The DAN unit was linked to a styrene-based monomer and copolymerized with styrene to form a polymer (PS-DAN) containing a controlled number of the DAAD recognition units. Likewise, a methacrylate monomer containing the UG unit was copolymerized with butyl methacrylate to form a polymer (PBMA-UG). Blends formed from PS-DAN and PBMA-UG were characterized by DSC, SEC, and viscometry. The importance of selective heterocomplexation and weak self-association in forming the blended networks was demonstrated by using a ureidopyrimidinone (UPy) unit, which also forms strong heterocomplexes with DAN but is able to strongly self-associate.

Original languageEnglish
Pages (from-to)6520-6521
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number18
DOIs
StatePublished - 11 May 2005
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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