Self-Assembly, Binding, and Dynamic Properties of Heterodimeric Porphyrin Macrocycles

A series of heterodimeric tetralactam macrocycles have been self-assembled using two kinetically labile zinc porphyrin-pyridine interactions. The stability constants have been determined by UV−vis titrations in CHCl3. The stability constants depend on the degree of preorganization of the linker unit...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-08, Vol.70 (17), p.6616-6622
Main Authors: Ballester, Pablo, Costa, Antoni, Deyà, Pere M, Frontera, Antonio, Gomila, Rosa M, Oliva, Ana I, Sanders, Jeremy K. M, Hunter, Christopher A
Format: Article
Language:English
Subjects:
Chemistry
Coordination compounds
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Inorganic chemistry and origins of life
Organic chemistry
Preparations and properties
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Summary:A series of heterodimeric tetralactam macrocycles have been self-assembled using two kinetically labile zinc porphyrin-pyridine interactions. The stability constants have been determined by UV−vis titrations in CHCl3. The stability constants depend on the degree of preorganization of the linker units connecting the interacting groups. The ability of the self-assembled macrocycles to bind a terephthalamide guest was also investigated. One of the macrocycles was used for the construction of a [2]rotaxane. The dynamic properties of this system provide insight into the exchange mechanisms that operate in complex noncovalent assemblies.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0505369