Bis(hydroxy-isoindolinone)s: synthesis, stereochemistry, polymer chemistry, and supramolecular assembly
Howard M Colquhoun1, Zhixue Zhu, Christine J Cardin
1Department of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, UK. h.m.colquhoun@rdg.ac.uk
Abstract:
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.
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