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Functionalized Phosphonated Half‐Cage Molecules as Ligands for Metal Complexes
Author(s) -
Villemin Elise,
Herent MarieFrance,
MarchandBrynaert Jacqueline
Publication year - 2012
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.201200806
Subject(s) - chemistry , molecule , ligand (biochemistry) , metal , cage , iodide , stoichiometry , stereochemistry , polymer chemistry , combinatorial chemistry , organic chemistry , biochemistry , receptor , mathematics , combinatorics
Phosphonated molecules, featuring a half‐cage structure and a N ‐lateral chain with additional metal coordinating groups were designed as ligands of metal cations. These compounds were synthesized by a Diels–Alder (DA) strategy, using 1‐diethoxyphosphoryl‐1,3‐butadiene and a series of N ‐substituted maleimides as dienophiles. Two cycloadducts, bearing a terminal primary alcohol and a terminal iodide, respectively, were used as key intermediates for further functionalizations. Metal coordination properties of the ligands equipped with functionalized N ‐lateral chains were proven by an ESI‐HRMS study. The stoichiometry of one selected Eu III complex with a diphosphonated ligand was determined by photoluminescence spectroscopy in emission mode.