Bis(hydroxy-isoindolinone)s: synthesis, stereochemistry, polymer chemistry, and supramolecular assembly.
Pseudoacid chlorides of 2,5-bis(4-fluorobenzoyl) terephthalic acid and 4,6-bis(4-fluorobenzoyl) isophthalic acid condense with primary amines to afford diastereomeric bis(hydroxyindolinone)s in good isolated yields and with diamines to give high molecular weight poly(hydroxyindolinone)s. Bis-N-pyrenemethyl bis(hydroxyindolinone)s assemble, even in dipolar solvents such as DMSO, with macrocyclic diimide-sulfones to give [3]pseudorotaxanes stabilized by electronically complementary aromatic pi-pi-stacking and shape-complementary van der Waals interactions.
Colquhoun
Howard M
HM
Department of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, UK. h.m.colquhoun@rdg.ac.uk
Zhu
Zhixue
Z
Cardin
Christine J
CJ
White
Andrew J P
AJ
Drew
Michael G B
MG
Gan
Yu
Y