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Fast and Convenient Divergent Synthesis of Aliphatic Ester Dendrimers by Anhydride Coupling
Abstract
A novel divergent approach was developed for the synthesis of dendritic aliphatic polyester structures using an acetal-protected anhydride derivative of 2,2-bis(hydroxymethyl)propionic acid as the acylating agent. This divergent synthesis is remarkable, because unlike all others, it only requires a small excess of reagent to achieve quantitative growth, and it requires no means of purification other than a simple solvent extraction or precipitation. A monodisperse sixth generation dendrimer with molecular weight of 30 711 Dalton and 192 masked hydroxyl groups was prepared in high yield and purity using 1,1,1-tris(hydroxyphenyl)ethane as the core molecule. Linear and star-shaped poly(ethylene glycol) (PEG) derivatives of narrow polydispersity were also used as core molecules in the divergent synthesis of dendritic-linear copolymer hybrids up to the fourth generation without requiring any chromatographic purification.
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Cited by
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Grayson, S. M., & Fréchet, J. M. J. (2001) · Chemical Reviews · doi:10.1021/cr990116h · Cited by 1,619
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Jain, K., Kesharwani, P., Gupta, U., & Jain, N. K. (2010) · International Journal of Pharmaceutics · doi:10.1016/j.ijpharm.2010.04.027 · Cited by 710
Stimuli-Responsive Supramolecular Assemblies of Linear-Dendritic Copolymers
Gillies, E. R., Jonsson, T. B., & Fréchet, J. M. J. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0463738 · Cited by 549
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Janaszewska, A., Lazniewska, J., Trzepiński, P., Marcinkowska, M., & Klajnert-Maculewicz, B. (2019) · Biomolecules · doi:10.3390/biom9080330 · Cited by 409
Metadata
- Authors
- Ihre, H., Padilla De Jesús, O. L., & Fréchet, J. M. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-06-01
- Volume
- 123
- Issue
- 25
- Pages
- 5908-5917
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2041051099
- Cited by
- 296
- References
- 0
- FWCI
- 12.35
- Type
- journal article
- Language
- en
- Open access
- closed
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- Ihre, H., Padilla De Jesús, O. L., & Fréchet, J. M. J. (2001). Fast and Convenient Divergent Synthesis of Aliphatic Ester Dendrimers by Anhydride Coupling. Journal of the American Chemical Society. https://doi.org/10.1021/ja010524e
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
