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Chloride‐Anion‐Templated Synthesis of a Strapped‐Porphyrin‐Containing Catenane Host System
Author(s) -
Brown Asha,
Langton Matthew J.,
Kilah Nathan L.,
Thompson Amber L.,
Beer Paul D.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502721
Subject(s) - catenane , chemistry , porphyrin , hydrogen bond , chloride , pyridine , titration , combinatorial chemistry , polymer chemistry , crystallography , inorganic chemistry , photochemistry , organic chemistry , molecule
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.