Bis(hydroxy-isoindolinone)s: synthesis, stereochemistry, polymer chemistry, and supramolecular assembly
Colquhoun, H. M., Zhu, Z., Cardin, C. J., White, A. J.P., Drew, M. G. B. and Gan, Y. (2010) Bis(hydroxy-isoindolinone)s: synthesis, stereochemistry, polymer chemistry, and supramolecular assembly. Organic Letters, 12 (17). pp. 3756-3759. ISSN 1523-7060
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To link to this article DOI: 10.1021/ol101338m
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 pseudorotaxanes stabilized by electronically complementary aromatic π−π-stacking and shape-complementary van der Waals interactions.