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Triggering Activity of Catalytic Rod‐Like Supramolecular Polymers
Author(s) -
Huerta Elisa,
van Genabeek Bas,
Lamers Brigitte A. G.,
Koenigs Marcel M. E.,
Meijer E. W.,
Palmans Anja R. A.
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.201405410
Subject(s) - moiety , supramolecular chemistry , supramolecular polymers , catalysis , polymer , substrate (aquarium) , aldol reaction , proline , polymer chemistry , chemistry , selectivity , benzene , materials science , stereochemistry , combinatorial chemistry , molecule , organic chemistry , biochemistry , amino acid , oceanography , geology
Supramolecular polymers based on benzene‐1,3,5‐tricarboxamides (BTAs) functionalized with an L ‐ or D ‐proline moiety display high catalytic activity towards aldol reactions in water. High turnover frequencies (TOF) of up to 27×10 −4 s −1 and excellent stereoselectivities (up to 96 % de , up to 99 % ee ) were observed. In addition, the catalyst could be reused and remained active at catalyst loadings and substrate concentrations as low as 0.1 mol % and 50 m M , respectively. A temperature‐induced conformational change in the supramolecular polymer triggers the high activity of the catalyst. The supramolecular polymer’s helical sense in combination with the configuration of the proline ( L ‐ or D ‐) is responsible for the observed selectivity.