Abstract
The synthesis and characterization of double porphyrin cage compounds are described. They consist of two porphyrins that are each attached to a diphenylglycoluril‐based clip molecule via four ethyleneoxy spacers, and are linked together by a single alkyl chain using “click”‐chemistry. Following a newly developed multistep synthesis procedure we report three of these double porphyrin cages, linked by spacers of different lengths, i.e. 3, 5, and 11 carbon atoms. The structures of the double porphyrin cages were fully characterized by NMR, which revealed that they consist of mixtures of two diastereoisomers. Their zinc derivatives are capable of forming sandwich‐like complexes with the ditopic ligand 1,4‐diazabicyclo[2,2,2]octane (dabco).
Highlights
In the past decades, nature has served as a source of inspiration for scientists working on the design of new molecular systems that are capable of mimicking the action of enzymes, e.g. with respect to rate and substrate selectivity
We have presented a multistep route for the synthesis of covalently linked double porphyrin cage compounds
For the synthesis of these compounds, a mono-bromo-substituted porphyrin was synthesized in 6 steps starting from paraformaldehyde and pyrrole
Summary
Nature has served as a source of inspiration for scientists working on the design of new molecular systems that are capable of mimicking the action of enzymes, e.g. with respect to rate and substrate selectivity. One of the factors contributing to the high replication fidelity of DNApolymerases is the fact that they make use of sequential processive catalysis, meaning that the enzyme stays bound to the substrate while it performs multiple rounds of consecutive reactions.[2] During these reactions the movement of the polymerase along the biopolymer chain is discrete and unidirectional, as it repeatedly moves one nucleotide further to carry out the reaction. In this way, information is reliably copied and stored again by making use of the four nucleobases present in the DNA chain
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