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Supramolecular Catalysis by Carboxylated Pillar[n]arenes
Author(s) -
Kosiorek Sandra,
Rad Nazar,
Sashuk Volodymyr
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000082
Subject(s) - supramolecular catalysis , supramolecular chemistry , catalysis , pillar , cucurbituril , chemistry , substrate (aquarium) , hydrolysis , nanotechnology , combinatorial chemistry , organic chemistry , polymer chemistry , materials science , molecule , oceanography , structural engineering , engineering , geology
Pillar[n]arenes constitute the most recognizable macrocyclic compounds discovered recently. So far, research has been focused on their binding properties, while the catalytic properties were poorly explored. Herein we present the study of the binding as well as the catalytic properties of pillar[5]‐ and pillar[6]arenes functionalized with carboxylic groups in water. We show that electrostatic stabilization is not the main driving force during the binding, however, it is crucial for catalysis. The macrocycles promote the hydrolysis of a wide variety of hydrazones, and their catalytic activity, in essence, is determined by the barrier of the passage of the substrate through the macrocyclic cavity. This opens up new perspectives for these macrocycles that could make a strong competition to traditional supramolecular catalysts such as cyclodextrins or cucurbiturils.