The synthesis and characterization of chiral dendrimer 1 in its racemic form is reported. The chirality of this macromolecule, with a molecular weight of 2831, is based on a pentaerythritol core, acting as a stereocenter with four dendritic substituents of different generation. The synthesis is making use of a newly developed, general route to a multisubstituted pentaerythritol derivative.Resolution of 1 is hampered by conformational flexibility. The latter, however, allows detailed 'H-NMR characterization indicating the stratified structure of the dendrimer. Considerable resolution of the 'H-NMR signals of the inner protons in c&6 and C~DSN suggests that 1 adopts an overall chiral shape in solution.
The synthesis and characterization of two chiral dendrimers, 1 and 2, in their racemic form is presented. The chirality is based on the construction of four constitutionally different, but chemically resembling, branches to an achiral core. A multi‐substituted pentaerythritol derivative is used as core and Fréchet's aromatic‐ether dendritic wedges of different generation are used as branches. The synthetic approach makes use of the consecutive attachment of the four branches by selective deprotection of the core. Both chiral dendrimers of different size have been synthesized from the same precursor. 1H‐NMR Spectroscopy indicates an overall chiral shape for 1, while for both 1 and 2 stratified structures are observed. Several attempts to resolve both dendrimers have not been successful so far, giving rise to a discussion on the degree of chirality in these dendrimers of nanometer dimensions.
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