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Rapid and efficient synthesis of aliphatic ester dendrons and dendrimers
KTH, Superseded Departments, Fibre and Polymer Technology.ORCID iD: 0000-0002-9200-8004
KTH, Superseded Departments, Fibre and Polymer Technology.ORCID iD: 0000-0002-8348-2273
KTH, Superseded Departments, Fibre and Polymer Technology.ORCID iD: 0000-0002-9372-0829
2002 (English)In: Macromolecules, ISSN 0024-9297, E-ISSN 1520-5835, Vol. 35, no 22, 8307-8314 p.Article in journal (Refereed) Published
Abstract [en]

A divergent approach to synthesize dendritic aliphatic polyester structures based on 2,2-bis(hydroxymethyl) propionic acid (bis-MPA) is described. The key building block is the anhydride of isopropylidene-2,2-bis(methoxy) propionic acid which is synthesized in high yields through self-dehydration, utilizing N,N'-dicyclohexylcarbodiimide (DCC) as reagent. The high reactivity of the anhydride toward hydroxyl groups makes the divergent synthesis of dendrimers and dendrons viable. Dendritic growth occurs in the presence of protecting groups sensitive toward hydrogenolysis, such as benzyl esters and ethers. The acetonide-protecting group is easily removed under acidic conditions using DOWEX 50W-X2 resin in methanol. Fourth-generation dendrons and dendrimers were successfully synthesized in high yields utilizing 1.3-1.5 equiv of anhydride per hydroxyl group. Common characteristics of the esterification reaction were short reaction time, mild reaction conditions, easy monitoring by NMR analysis, and simple workup. This synthetic approach opens up the possibility to utilize orthogonal protecting groups of acetonide-protected 2,2-bis(hydroxymethyl) propionic anhydride as a novel building block.

Place, publisher, year, edition, pages
2002. Vol. 35, no 22, 8307-8314 p.
Keyword [en]
Carboxylic acids, Dehydration, Esterification, Methanol, Nuclear magnetic resonance spectroscopy, Polyesters, Resins, Synthesis (chemical)
National Category
Chemical Engineering
Identifiers
URN: urn:nbn:se:kth:diva-13159DOI: 10.1021/ma0205360ISI: 000178738000011OAI: oai:DiVA.org:kth-13159DiVA: diva2:321553
Note
QC 20100601Available from: 2010-06-01 Created: 2010-05-31 Last updated: 2017-12-12Bibliographically approved
In thesis
1. New approaches in synthesis and characterization of dendritic macromolecules based on bis-mpa
Open this publication in new window or tab >>New approaches in synthesis and characterization of dendritic macromolecules based on bis-mpa
2003 (English)Doctoral thesis, comprehensive summary (Other scientific)
Place, publisher, year, edition, pages
Stockholm: KTH, 2003. 62 p.
Keyword
dendritic aliphatic polyeester, anhydride chemistry, divergent growth, dendronized polymers
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-3578 (URN)
Public defence
2003-06-17, 00:00 (English)
Note
QC 20100531Available from: 2003-06-26 Created: 2003-06-26 Last updated: 2010-06-01Bibliographically approved

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Malkoch, MichelMalmström, EvaHult, Anders

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