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Rapid and efficient synthesis of aliphatic ester dendrons and dendrimers
KTH, Tidigare Institutioner                               , Fiber- och polymerteknologi.ORCID-id: 0000-0002-9200-8004
KTH, Tidigare Institutioner                               , Fiber- och polymerteknologi.ORCID-id: 0000-0002-8348-2273
KTH, Tidigare Institutioner                               , Fiber- och polymerteknologi.ORCID-id: 0000-0002-9372-0829
2002 (engelsk)Inngår i: Macromolecules, ISSN 0024-9297, E-ISSN 1520-5835, Vol. 35, nr 22, s. 8307-8314Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2002. Vol. 35, nr 22, s. 8307-8314
Emneord [en]
Carboxylic acids, Dehydration, Esterification, Methanol, Nuclear magnetic resonance spectroscopy, Polyesters, Resins, Synthesis (chemical)
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-13159DOI: 10.1021/ma0205360ISI: 000178738000011OAI: oai:DiVA.org:kth-13159DiVA, id: diva2:321553
Merknad
QC 20100601Tilgjengelig fra: 2010-06-01 Laget: 2010-05-31 Sist oppdatert: 2017-12-12bibliografisk kontrollert
Inngår i avhandling
1. New approaches in synthesis and characterization of dendritic macromolecules based on bis-mpa
Åpne denne publikasjonen i ny fane eller vindu >>New approaches in synthesis and characterization of dendritic macromolecules based on bis-mpa
2003 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
sted, utgiver, år, opplag, sider
Stockholm: KTH, 2003. s. 62
Emneord
dendritic aliphatic polyeester, anhydride chemistry, divergent growth, dendronized polymers
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-3578 (URN)
Disputas
2003-06-17, 00:00 (engelsk)
Merknad
QC 20100531Tilgjengelig fra: 2003-06-26 Laget: 2003-06-26 Sist oppdatert: 2010-06-01bibliografisk kontrollert

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