Supramolecular polymer chemistry: Self-assembling dendrimers using the DDA·AAD (GC-like) hydrogen bonding motif

Yuguo Ma, Sergei V. Kolotuchin, Steven C Zimmerman

Research output: Contribution to journalArticle

Abstract

Heterocyclic unit 2 containing complementary donor-donor-acceptor (DDA) and acceptor-acceptor-donor (AAD) hydrogen bonding arrays at an angle of about 60° was designed to self-assemble into a hexamer. To investigate whether this unit could self-assemble dendrimers, the 2,8-diamino-2-N-ethylpyrimido-(4,5-b)(1,8)naphthyridine-3H-4-one subunit was synthesized with a first (2a), second (2b), and third generation (2c) Fréchet-type dendron attached to the 8-amino group. The synthesis of 2a-c was accomplished in 11 steps beginning with 2,6-diaminopyridine and the corresponding dendron bromide. Studies using 1H NMR, size exclusion chromatography (SEC), and dynamic light scattering (DLS) support the cooperative formation of cyclic hexamers in apolar solvents. The stability of the self-assembled dendrimers is dependent on the size of the attached dendron, and mixing studies with 2a-c indicate their usefulness in constructing dynamic combinatorial libraries.

Original languageEnglish (US)
Pages (from-to)13757-13769
Number of pages13
JournalJournal of the American Chemical Society
Volume124
Issue number46
DOIs
StatePublished - Nov 20 2002

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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