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Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases

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Introducing a rigid linear π-conjugated acetylene linker into a supramolecular building block consisting of a hydrogen-bond donor side and a hydrogen-bond acceptor side yields a decrease in cooperativity in the resulting formed quartet. This follows from our Kohn-Sham molecular orbital and Voronoi deformation density analyses of hydrogen-bonded macrocycles based on guanine and cytosine nucleobases. The acetylene linker abstracts electron density from the hydrogen-bond acceptor and donor, making the hydrogen-bond acceptor more negatively charged and the hydrogen-bond donor more positively charged and hence suppressing the donor–acceptor charge transfer interaction between the interacting fragments. This, ultimately, hampers the cooperativity in the hydrogen-bonded macrocycle. We envision that these findings could open the door to new design principles for the development of novel hydrogen-bond supramolecular macrocycles.

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European Journal of Organic Chemistry, 2024, p. e202301164

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cc-by-nc-nd (c) Almacellas, David, et al., 2024

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Articles publicats en revistes (Química Inorgànica i Orgànica)

# metadata.dc.title[].value
Cooperativity in Hydrogen-Bonded Macrocycles Derived from Nucleobases