Design, synthesis, and characterization of conifer-shaped dendritic architectures

An elongated structural design leading to more conical-shaped dendritic architectures by using a combination of 1-->3, 1-->(2+1), and 1-->(2+1 Me) C-branched monomers is presented. Synthesis of the conifer-shaped macromolecule was achieved by reaction between isocyanate 20 and amine 26 in dry CH2Cl2. A resultant extended focal adamantane-modified dendron was deprotected to generate the water-soluble product, which was subsequently complexed with beta-cyclodextrin in D2O to create the desired tree-like product. Host-guest interactions of the adamantane moiety with the beta-cyclodextrin cavity were monitored by 1H NMR spectroscopy. All monomers, key intermediates, and final products were fully characterized by 1H and 13C NMR spectroscopy, ESI or MALDI-TOF mass spectrometry, and IR spectroscopy.