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Dendritic Structures Based on Bis(hydroxymethyl)propionic Acid as Platforms for Surface Reactions
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Surface Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Surface Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.ORCID iD: 0000-0002-9200-8004
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2005 (English)In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 21, no 10, 4512-4519 p.Article in journal (Refereed) Published
Abstract [en]

In this paper we present results related to the self-assembly of different generations of disulfide-cored 2,2-bis(hydroxymethyl)propionic acid-based dendritic structures onto gold surfaces. These molecular architectures, ranging from generation 1 to generation 3, contain removable acetonide protecting groups at their periphery that are accessible for hydrolysis with subsequent formation of OH-terminated surface-attached dendrons. The deprotection has been investigated in detail as a versatile approach to accomplish reactive surface platforms. A special focus has been devoted to the comparison of the properties of the layers formed by hydrolysis of the acetonide moieties directly on the surface and in solution, prior to the layer formation.

Place, publisher, year, edition, pages
2005. Vol. 21, no 10, 4512-4519 p.
Keyword [en]
Carboxylic acids; Dendrimers; Fourier transform infrared spectroscopy; Gold; Hydrolysis; Molecular structure; Self assembly; Absorbates; Acetonide moieties; Dendritic structures; Supramolecular reactions; Surface reactions
National Category
Polymer Chemistry Physical Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-7707DOI: 10.1021/la047077bISI: 000228983700040Scopus ID: 2-s2.0-18844439420OAI: oai:DiVA.org:kth-7707DiVA: diva2:12812
Note
QC 20100826Available from: 2007-11-23 Created: 2007-11-23 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Tuning Properties of Surfaces and Nanoscopic Objects using Dendronization and Controlled Polymerizations
Open this publication in new window or tab >>Tuning Properties of Surfaces and Nanoscopic Objects using Dendronization and Controlled Polymerizations
2007 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

In this study, dendronization and grafting via controlled polymerization techniques, atom transfer radical polymerization (ATRP) and ring-opening polymerization (ROP), have been explored. Modification of surfaces and cellulose using these techniques, which enable grafting of well-defined polymer architectures, has been investigated. The interest in using cellulose stems from its renewability, biocompatibility, high molecular weight, and versatile functionalization possibilities.

Dendronization was performed using disulfide-cored didendrons of 2,2-bis(methylol)propionic acid (bis-MPA) on gold surfaces, for the formation of self-assembled monolayers. It was found that the height of the monolayer increased with increasing dendron generation and that the end-group functionality controlled the wettability of the modified surface.

Superhydrophobic cellulose surfaces could be obtained when a ‘graft-on-graft’ architecture was obtained using ATRP from filter paper after subsequent post-functionalized using a perfluorinated compound. The low wettability could be explained by a combination of a high surface roughness and the chemical composition.

Biobased dendronized polymers were synthesized through the ‘attach to’ route employing dendronization of soluble cellulose, in the form of hydroxypropyl cellulose (HPC). The dendronized polymers were studied as nanosized objects using atomic force microscopy (AFM) and it was found that the dendron end-group functionality had a large effect on the molecular conformation on surfaces of spun cast molecules.

ATRP of vinyl monomers was conducted from an initiator-functionalized HPC and an initiator-functionalized first generation dendron, which was attached to HPC. The produced comb polymers showed high molecular weight and their sizes could be estimated via AFM of spun cast molecules on mica and from dynamic light scattering in solution, to around 100-200 nm. The comb polymers formed isoporous membranes, exhibiting pores of a few micrometers, when drop cast from a volatile solvent in a humid environment. HPC was also used to initiate ROP of ε-caprolactone, which was chain extended using ATRP to achieve amphiphilic comb block copolymers. These polymers could be suspended in water, cross-linked and were able to solubilize a hydrophobic compound.

Place, publisher, year, edition, pages
Stockholm: KTH, 2007. 70 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2007:83
Keyword
Dendrimers, dendronized polymers, cellulose, Atom Transfer Radical Polymerization, Ring-Opening Polymerization, surface modification, grafting, superhydrophobic, amphiphilic polymer, block copolymer, Atomic Force Microscopy
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-4550 (URN)978-91-7178-820-7 (ISBN)
Public defence
2007-12-14, D3, Huvudbyggnaden, Lindstedtsvägen 5, Stockholm, 14:00
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Note
QC 20100826Available from: 2007-11-23 Created: 2007-11-23 Last updated: 2010-08-26Bibliographically approved

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Malkoch, MichaelMalmström, EvaBlomberg, Eva

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