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Chloride-Anion-Templated Synthesis of a Strapped-Porphyrin-Containing Catenane Host System.

ABSTRACT: The synthesis, structure and anion-recognition properties of a new strapped-porphyrin-containing [2]catenane anion host system are described. The assembly of the catenane is directed by discrete chloride anion templation acting in synergy with secondary aromatic donor-acceptor and coordinative pyridine-zinc interactions. The [2]catenane incorporates a three-dimensional, hydrogen-bond-donating anion-binding pocket; solid-state structural analysis of the catenane?chloride complex reveals that the chloride anion is encapsulated within the catenane's interlocked binding cavity through six convergent CH????Cl and NH???Cl hydrogen-bonding interactions and solution-phase (1) H?NMR titration experiments demonstrate that this complementary hydrogen-bonding arrangement facilitates the selective recognition of chloride over larger halide anions in DMSO solution.

SUBMITTER: Brown A

PROVIDER: S-EPMC4691337 | biostudies-other | 2015 Dec

REPOSITORIES: biostudies-other

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Chloride-Anion-Templated Synthesis of a Strapped-Porphyrin-Containing Catenane Host System.

Brown Asha A Langton Matthew J MJ Kilah Nathan L NL Thompson Amber L AL Beer Paul D PD

Chemistry (Weinheim an der Bergstrasse, Germany) 20151028 49

The synthesis, structure and anion-recognition properties of a new strapped-porphyrin-containing [2]catenane anion host system are described. The assembly of the catenane is directed by discrete chloride anion templation acting in synergy with secondary aromatic donor-acceptor and coordinative pyridine-zinc interactions. The [2]catenane incorporates a three-dimensional, hydrogen-bond-donating anion-binding pocket; solid-state structural analysis of the catenane⋅chloride complex reveals that the ...[more]

PMID: 26508679

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