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Positive Allosteric Control of Guests Encapsulation by Metal Binding to Covalent Porphyrin Cages
Author(s) -
Djemili Ryan,
Kocher Lucas,
Durot Stéphanie,
Peuronen Anssi,
Rissanen Kari,
Heitz Valérie
Publication year - 2019
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.201805498
Subject(s) - allosteric regulation , porphyrin , pyrazine , chemistry , molecule , covalent bond , metal , crystallography , metal ions in aqueous solution , zinc , stereochemistry , receptor , photochemistry , organic chemistry , biochemistry
Abstract The allosteric control of the receptor properties of two flexible covalent cages is reported. These receptors consist of two zinc(II) porphyrins connected by four linkers of two different sizes, each incorporating two 1,2,3‐triazolyl ligands. Silver(I) ions act as effectors, responsible for an on/off encapsulation mechanism of neutral guest molecules. Binding silver(I) ions to the triazoles opens the cages and triggers the coordination of pyrazine or the encapsulation of N , N ′‐dibutyl‐1,4,5,8‐naphthalene diimide. The X‐ray structure of the silver(I)‐complexed receptor with short connectors is reported, revealing the hollow structure with a cavity well‐defined by two eclipsed porphyrins. Rather unexpectedly, the crystallographic structure of this receptor with pyrazine as a guest molecule showed that the cavity is occupied by two pyrazines, each binding to the zinc(II) porphyrin in a monotopic fashion.