Supramolecular dendritic π-conjugated systems: synthesis of glycinylurea functionalized π-conjugated diphenylanthracene guests and their complexation with dendritic hosts. Part I

Florina S. Precup, Albertus P.H.J. Schenning, Edbert W. Meijer, Gheorghe Hubca

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Glycinylurea functionalized π-conjugated diphenylanthracene guests (DPA guests) that bind to adamantyl urea modified dendritic hosts were synthesized and fully characterized by NMR spectroscopy (1H-NMR, 13C-NMR) and MALDI-TOF-MS. The resulting supramolecular assemblies have been investigated with respect to their binding properties. DPA guests molecules were able to click into urea functionalized N,N-bis[(3-adamantyl ureido) propyl] methyl amine host as a result of acid-base (between COOH of the guest and amines of the host) and hydrogen bonding interactions (between the urea linkages of dendrimer and the guest). The guest molecules were bound as 1:1 inclusion complexes and the association constants for both guests have been calculated. Subsequently, an adamantyl urea modified fifth generation poly(propylene imine) dendrimer was synthesized as a multivalent host which contains 32 N,Nbis[(3-adamantyl ureido) propyl] amine binding sites. Size exclusion chromatography showed that 32 of the DPA guests strongly bind to the fifth generation adamantyl functionalized dendritic host.

Original languageEnglish
Pages (from-to)133-140
Number of pages8
JournalRevista de Chimie
Volume58
Issue number2
Publication statusPublished - Feb 2007

Keywords

  • "Click-in" concept
  • Binding properties
  • Dendrimers
  • Guest
  • Host
  • Supramolecular assemblies

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