Avoiding Steric Congestion in Dendrimer Growth through Proportionate Branching: A Twist on da Vinci’s Rule of Tree Branching

Making defect-free macromolecules is a challenging issue in chemical synthesis. This challenge is especially pronounced in dendrimer synthesis where exponential growth quickly leads to steric congestion. To overcome this difficulty, proportionate branching in dendrimer growth is proposed. In proport...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-10, Vol.77 (20), p.8879-8887
Main Authors: Yue, Xuyi, Taraban, Marc B, Hyland, Laura L, Yu, Yihua Bruce
Format: Article
Language:English
Subjects:
Applied sciences
Dendrimers - chemical synthesis
Dendrimers - chemistry
Exact sciences and technology
Fluorocarbons - chemical synthesis
Fluorocarbons - chemistry
Molecular Structure
Organic polymers
Physicochemistry of polymers
Polymers with particular structures
Preparation, kinetics, thermodynamics, mechanism and catalysts
Propionates - chemical synthesis
Propionates - chemistry
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Summary:Making defect-free macromolecules is a challenging issue in chemical synthesis. This challenge is especially pronounced in dendrimer synthesis where exponential growth quickly leads to steric congestion. To overcome this difficulty, proportionate branching in dendrimer growth is proposed. In proportionate branching, both the number and the length of branches increase exponentially but in opposite directions to mimic tree growth. The effectiveness of this strategy is demonstrated through the synthesis of a fluorocarbon dendron containing 243 chemically identical fluorine atoms with a MW of 9082 Da. Monodispersity is confirmed by nuclear magnetic resonance spectroscopy, mass spectrometry, and small-angle X-ray scattering. Growing different parts proportionately, as nature does, could be a general strategy to achieve defect-free synthesis of macromolecules.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo301718y