Molecular Tweezers with Freely Rotating Linker and Porphyrin Moieties

Rhys Murphy, Duc-Truc Pham, Stephen Lincoln, Martin Johnston

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    Molecular tweezers were synthesised by using a microwave accelerated alkene plus cyclobutane epoxide reaction between norbornyl appended porphyrin moieties and a diepoxide functionalised phenyl diimide spacer. The tweezers contain several rotational degrees of freedom; about the porphyrin with respect to the norbornyl linker, and between the two norbornyl backbone sections. The ability of ZnII metallated tweezer 1 to complex 1,4-diazabicyclo[2.2.2]octane (DABCO) was studied by UV/Vis and 1H NMR spectroscopy and multivariate global spectral analysis. The system was found to form a strong 1:1 intramolecular complex (1:DABCO) with an association constant of K11 = 8.1 × 107 M-1, transforming to a 1:2 open complex [1:(DABCO)2] with K12 = 2.7 × 109 M -2 at high concentrations of DABCO. Usually molecular tweezers possess a high degree of preorganisation, but we have found that the introduction of several rotational degrees of freedom has little impact on association constant strength.

    Original languageEnglish
    Pages (from-to)2985-2993
    Number of pages9
    JournalEuropean Journal of Organic Chemistry
    Volume2013
    Issue number15
    DOIs
    Publication statusPublished - 2013

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