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An Octa‐Urea [Pd 2 L 4 ] 4+ Cage that Selectively Binds to n‐ octyl‐α‐D‐Mannoside
Author(s) -
Schaapkens Xander,
Holdener Joël H.,
Tolboom Jens,
Bobylev Eduard O.,
Reek Joost N. H.,
Mooibroek Tiddo J.
Publication year - 2021
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.202100229
Subject(s) - chemistry , supramolecular chemistry , urea , molecular recognition , selectivity , affinities , binding affinities , glycoside , stereochemistry , molecule , organic chemistry , receptor , catalysis , biochemistry
Designing compounds for the selective molecular recognition of carbohydrates is a challenging task for supramolecular chemists. Macrocyclic compounds that incorporate isophtalamide or bisurea spacers linking two aromatic moieties have proven effective for the selective recognition of all‐equatorial carbohydrates. Here, we explore the molecular recognition properties of an octa‐urea [Pd 2 L 4 ] 4+ cage complex ( 4 ). It was found that small anions like NO 3 − and BF 4 − bind inside 4 and inhibit binding of n ‐octyl glycosides. When the large non‐coordinating anion ‘BAr F ’ was used, 4 showed excellent selectivity towards n ‐octyl‐α‐D‐Mannoside with binding in the order of K a ≈16 M −1 versus non‐measurable affinities for other glycosides including n ‐octyl‐β‐D‐Glucoside (in CH 3 CN/H 2 O 91 : 9).