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A Highly Stable Quadruply Hydrogen-Bonded Heterocomplex Useful for Supramolecular Polymer Blends
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 x 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.
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Cited by
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Yan, X., Wang, F., Zheng, B., & Huang, F. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35091b · Cited by 1,631
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Characterization of supramolecular gels
Yu, G., Yan, X., Han, C., & Huang, F. (2013) · Chemical Society Reviews · doi:10.1039/c3cs60080g · Cited by 626
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Biedermann, F., & Schneider, H.-J. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00583 · Cited by 554
Yu, G., Zhou, X., Zhang, Z., Han, C., Mao, Z., Gao, C., & Huang, F. (2012) · Journal of the American Chemical Society · doi:10.1021/ja3099905 · Cited by 486
Metadata
- Authors
- Park, T., Zimmerman, S. C., & Nakashima, S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-04-16
- Volume
- 127
- Issue
- 18
- Pages
- 6520-6521
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2138957868
- Cited by
- 208
- References
- 0
- FWCI
- 6.75
- Type
- journal article
- Language
- en
- Open access
- closed
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- Park, T., Zimmerman, S. C., & Nakashima, S. (2005). A Highly Stable Quadruply Hydrogen-Bonded Heterocomplex Useful for Supramolecular Polymer Blends. Journal of the American Chemical Society. https://doi.org/10.1021/ja050996j
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