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Second Generation Calix[6]trenamides – Highly Selective Graftable Receptors for Neutral Guests and Contact Ion Pairs
Author(s) -
Lascaux Angélique,
Delahousse Guillaume,
Ghostin Jean,
Bouillon JeanPhilippe,
Jabin Ivan
Publication year - 2011
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/ejoc.201100673
Subject(s) - chemistry , calixarene , receptor , ammonium , lysine , combinatorial chemistry , stereochemistry , ion , molecule , organic chemistry , amino acid , biochemistry
With the aim of designing graftable calix[6]tren‐based receptors, calix[6]trenamides decorated with an appended functional arm were synthesized through [1+1] macrocyclization reactions between calix[6]trisamines and NTA‐lysine derivatives. NMR spectroscopy and ESI‐MS studies showed that one of these calix[6]trenamides, 5 , behaves as a unique heteroditopic receptor towards charged or neutral species. Notably, it can selectively bind contact ammonium fluoride salts through a highly cooperative process. In addition, acid–base control of its binding properties was clearly evidenced. This second generation of graftable receptors opens new perspectives in the design of sensors for charged or neutral species.