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Starburst Dendrimers: Molecular-Level Control of Size, Shape, Surface Chemistry, Topology, and Flexibility from Atoms to Macroscopic Matter†
Dr. Donald A. Tomalia,
Dr. Adel M. Naylor,
Prof. William A. Goddard III,
Corresponding Author
Dr. Donald A. Tomalia
Applied Organic and Functional Polymers Research, The Dow Chemical Company, Midland, MI 48674 (USA)
Michigan Molecular Institute 1910 W. St. Andrews Road, Midland. MI 48640 (USA)Search for more papers by this authorDr. Adel M. Naylor
Arthur Amos Noyes Laboratory of Chemical Physics, California Institute of Technology Pasadena, CA 91125 (USA)
Search for more papers by this authorProf. William A. Goddard III
Arthur Amos Noyes Laboratory of Chemical Physics, California Institute of Technology Pasadena, CA 91125 (USA)
Search for more papers by this authorDr. Donald A. Tomalia,
Dr. Adel M. Naylor,
Prof. William A. Goddard III,
Corresponding Author
Dr. Donald A. Tomalia
Applied Organic and Functional Polymers Research, The Dow Chemical Company, Midland, MI 48674 (USA)
Michigan Molecular Institute 1910 W. St. Andrews Road, Midland. MI 48640 (USA)Search for more papers by this authorDr. Adel M. Naylor
Arthur Amos Noyes Laboratory of Chemical Physics, California Institute of Technology Pasadena, CA 91125 (USA)
Search for more papers by this authorProf. William A. Goddard III
Arthur Amos Noyes Laboratory of Chemical Physics, California Institute of Technology Pasadena, CA 91125 (USA)
Search for more papers by this author†
STARBURST is a registered trademark of The Dow Chemical Company.
Graphical Abstract
The synthesis of starburst polyamidoamines can be initiated by the addition of ammonia to methyl acrylate in a 1:3 ratio. The resulting triester is then treated with ethylenediamine in large excess, thereby affording a dendrimer of generation 0 containing three terminal NH2 groups. Reiteration of the two reactions leads 10 higher generations (generation 2 is shown here). Ideal growth results in dendrimers having a defined number of surface groups, which, in turn, may be modified chemically.
Abstract
Starburst dendrimers are three-dimensional, highly ordered oligomeric and polymeric compounds formed by reiterative reaction sequences starting from smaller molecules—“initiator cores” such as ammonia or pentaerythritol. Protecting group strategies are crucial in these syntheses, which proceed via discrete “Aufbau” stages referred to as generations. Critical molecular design parameters (CMDPs) such as size, shape, and surface chemistry may be controlled by the reactions and synthetic building blocks used. Starburst dendrimers can mimic certain properties of micelles and liposomes and even those of biomolecules and the still more complicated, but highly organized, building blocks of biological systems. Numerous applications of these compounds are conceivable, particularly in mimicking the functions of large biomolecules as drug carriers and immunogens. This new branch of “supramolecular chemistry” should spark new developments in both organic and macromolecular chemistry.
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