Aggregates of calix[4]arenes based on the 2,6‐diaminotriazine · imide system
Author(s) -
Vreekamp Remko H.,
Verboom Willem,
Reinhoudt David N.
Publication year - 1996
Publication title -
recueil des travaux chimiques des pays‐bas
Language(s) - English
Resource type - Journals
ISSN - 0165-0513
DOI - 10.1002/recl.19961150705
Subject(s) - hydrogen bond , intramolecular force , calixarene , chloroform , chemistry , intermolecular force , imide , uracil , polymer chemistry , stereochemistry , molecule , organic chemistry , dna , biochemistry
The synthesis of several calix[4]arenes functionalized with uracil or diaminotriazine moieties is described. The association between these complementary calix[4]arenes is strongly influenced by processes related to the position and directionality of the hydrogen‐bonding moieties. In the case of bis(uracil)calix[4]arene ( 4 ), self‐association is observed ( K = 3.4 · 10 3 M −1 in CDCl 3 ) whereas, in the case of bis(diamidotriazine)calix[4]arene ( 16 ), it was concluded from 1 H‐NMR studies that intermolecular association is hampered by the formation of intramolecular hydrogen bonds. Due to the divergent orientation of the hydrogen‐bonding groups of bis(diaminotriazine)calix[4]arene ( 15b ), it forms hydrogen‐bonded strands through interaction with 5‐ethyl‐5‐phenylbarbituric acid ( 17 ), resulting in the formation of a gel in chloroform.
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