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A new rigid benzene‐bridged macrotricyclic ligand
Author(s) -
Krakowiak Krzysztof E.,
Xue Guoping,
Bradshaw Jerald S.,
Dalley N. Kent,
Nazarenko Alexander Y.,
Zhang Xian X.,
Izatt Reed M.
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370408
Subject(s) - chemistry , ligand (biochemistry) , benzene , stereochemistry , polymer chemistry , organic chemistry , receptor , biochemistry
A macrotricyclic ligand composed of two benzene rings connected by four 2,2′‐oxydiphenoxide bridges ( 2 ) has been prepared by treating 1,2,4,5‐tetrakis[2‐(2‐hydroxyphenoxy)phenoxymethyl]benzene with 1,2,4,5‐tetrakis(bromomethyl)benzene in acetonitrile in the presence of potassium carbonate. Ligand 2 is of interest because of its similarity to macrocycle 1 which interacts strongly with cesium ions. The proposed more direct route of treating an excess of 2,2′‐oxydiphenol with 1,2,4,5‐tetrakis(bromomethyl)benzene to prepare 2 did not give the desired macrocycle but gave bis(tribenzo‐11‐crown‐3) ( 8 ). An X‐ray crystal structure study of 2 showed that the benzene rings which are linked by the four 2,2′‐oxydiphenoxide bridges are connected in a nonsymmetric pattern. The structure of 8 was also determined using X‐ray diffraction methods, and is reported.