Extremely strong contiguous hydrogen bonding arrays

Research output: ThesisDoctoral Thesis

Abstract

When multiple hydrogen bonds lie in-plane and parallel to each other in close proximity, they experience additional positive or negative secondary electrostatic interactions. When a pair of molecules are arranged such that every hydrogen bond acceptor is on one molecule and every hydrogen bond donor is on another, the positive secondary electrostatic interactions are maximised, and thus the association constant of the complex is enhanced. This thesis will present the development of a family of quadruple hydrogen bonded complexes containing only positive secondary interactions, which confers unprecedented stability. The complexes are sufficiently stable to maintain strong binding in polar solvents such as acetonitrile and can be switched “on” and “off” with acid and base. They will be developed into synthons for acid-base responsive supramolecular recognition, for use in stimuli-responsive supramolecular polymers and gelators.
Original languageEnglish
QualificationPhD
Awarding Institution
  • University of Edinburgh
Award date29 Jun 2013
Place of PublicationEdinburgh
Publication statusPublished - 29 Jun 2013
Externally publishedYes

Keywords

  • hydrogen bonds
  • electrostatic interactions
  • bonding arrays

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  • Research Output

    AAAA-DDDD quadruple hydrogen-bond arrays featuring NH···N and CH···N hydrogen bonds

    Leigh, D. A., Robertson, C. C., Slawin, A. M. Z. & Thomson, P. I. T., 3 Jul 2013, In : Journal of the American Chemical Society . 135, 26, p. 9939-9943 5 p.

    Research output: Contribution to journalArticle

    Open Access
  • 41 Citations (Scopus)

    An AAAA–DDDD quadruple hydrogen-bond array

    Blight, B. A., Hunter, C. A., Leigh, D. A., McNab, H. & Thomson, P. I. T., 21 Feb 2011, In : Nature Chemistry. 3, p. 244-48 5 p.

    Research output: Contribution to journalArticle

  • 104 Citations (Scopus)

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