Toward poly(aminophthalimide), structures of dimers and trimers

H. Katayama, T.F.A. Greef, de, H. Kooijman, A.L. Spek, J.A.J.M. Vekemans, E.W. Meijer

Research output: Contribution to journalArticleAcademicpeer-review

6 Citations (Scopus)

Abstract

Poly(aminophthalimide) (PAP) dimers and trimers have been synthesized by palladium-catalyzed cross-coupling reactions of 3-aminophthalimides with 3-chloro- and 3,6-dichlorophthalimide, respectively. When Pd(OAc)2, XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), and K3PO4 are used, the C–N bond-forming reactions proceed quantitatively. The structures of those oligomers are examined by experimental and theoretical techniques including NMR, IR, single-crystal X-ray diffraction, and DFT calculations. The strong preference for cisoid structure of the diphthalimidylamine unit bearing a bifurcate hydrogen bonding is disclosed. Therefore, the aminophthalimide backbone is a highly promising candidate for the construction of a dynamically ordered helical structure.
Original languageEnglish
Pages (from-to)6642-6653
JournalTetrahedron
Volume63
Issue number28
DOIs
Publication statusPublished - 2007

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