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A Modular Approach to Potential Synthetic Receptors with Large Surfaces Based on Crown[ n ]cavitands
Author(s) -
Higler Irene,
Boerrigter Harold,
Verboom Willem,
Kooijman Huub,
Spek Anthony L.,
Reinhoudt David N.
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199808)1998:8<1597::aid-ejoc1597>3.0.co;2-1
Subject(s) - cavitand , chemistry , alkylation , bridging (networking) , calixarene , aromaticity , molecule , host–guest chemistry , crown (dentistry) , stereochemistry , combinatorial chemistry , organic chemistry , supramolecular chemistry , medicine , dentistry , computer network , computer science , catalysis
Crown[ n ]cavitands were synthesized by alkylation of tetrahydroxycavitands with polyethyleneglycol ditosylates. The bridging of two hydroxy groups at adjacent aromatic rings by a pentaethyleneglycol unit is favored over the bridging of two hydroxy groups at opposite aromatic rings. The presence of a sodium base enhances the formation of the 1,2‐crown[ n ]cavitand and improves the yield. The combination of 1,2‐crown[6]cavitands with calix[4]arenes or resorcin[4]arenes resulted in potential receptor molecules with large hydrophobic surfaces.