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Dendrimers in Action : Structure, Dynamics and Functionalization of Poly(Propylene Imine) Dendrimers

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Dendrimers in Action : Structure, Dynamics and Functionalization of Poly(Propylene Imine) Dendrimers Dendrimers in action : structure, dynamics and functionalization of poly(propylene imine) dendrimers Citation for published version (APA): Bosman, A. W. (1999). Dendrimers in action : structure, dynamics and functionalization of poly(propylene imine) dendrimers. Technische Universiteit Eindhoven. https://doi.org/10.6100/IR523548 DOI: 10.6100/IR523548 Document status and date: Published: 01/01/1999 Document Version: Publisher’s PDF, also known as Version of Record (includes final page, issue and volume numbers) Please check the document version of this publication: • A submitted manuscript is the version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website. • The final author version and the galley proof are versions of the publication after peer review. • The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal. If the publication is distributed under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license above, please follow below link for the End User Agreement: www.tue.nl/taverne Take down policy If you believe that this document breaches copyright please contact us at: [email protected] providing details and we will investigate your claim. Download date: 04. Oct. 2021 Tonny. Bosman Dendrimers in Action Structure, Dynamics, and Functionalization of Poly(propylene imine) Dendrimers Dendrimers in Action Structure, Dynamics, and Functionalization of Poly(propylene imine) Dendrimers PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Technische Universiteit Eindhoven, op gezag van de Rector Magnificus, prof.dr. M. Rem, voor een commissie aangewezen door het College voor Promoties in het openbaar te verdedigen op vrijdag 18 juni 1999 om 16.00 uur door Anton Willem Bosman geboren te Nijmegen Dit proefschrift is goedgekeurd door de promotoren: prof.dr. E.W. Meijer en prof.dr. D.A. Tomalia Copromotor: dr.ir. R.A.J. Janssen This research has been fmancially supported by the Council for Chemical Sciences ofthe Netherlands Organization for Scientific Research (CW-NWO). Cover design: Tonny Bosman, Ben Mobach Druk: Universiteitsdrukkerij, Technische Universiteit Eindhoven. CIP-DATA LIBRARY TECHNISCHE UNIVERSITEIT EINDHOVEN Bosman, Anton W. Dendrimers in action: strueture, dynamics and funetionalization of poly(propylene imine) dendrimers I by Anton W. Bosman.- Eindhoven: Technische Universiteit Eindhoven, 1999 Proefschrift.- ISBN 90-386-2561-8 NUGI813 Trefwoorden: dendrimeren I supramoleculaire structuren I nanostructuren Subject headings: dendrimers I supramolecular structures I nanostruetures die Chemie allein macht es nicht... H. Ringsdorf Ik schrijf mijn eigen lied ... A. Hazes in "Zij gelooft in mij" Aan mijn ouders VoorAnke Table of Contents Chapterl About Dendrimers 1 1.1 Introduetion 2 1.2 The Purity of Dendrimers 2 1.3 The Physical Behavior of Dendritic Molecules 6 1.3.1 Localization of End Groups in Dendrimers 6 1.3.2 Dendrimers versus Linear Macromolecules 12 1.3.3 Lower versus Higher Generation Dendrimers 14 1.3.4 The Behavior of Dendrimers on Surfaces and in Amphiphilic Materials 16 1.4 Aim and Scope of the Thesis 21 1.5 References and Notes 23 Chapter2 Soft-Core Dense-Shell Dendrimers 29 2.1 Introduetion 30 2.2 Topological Trapping ofFunctionalities in the Dendritic Box 31 2.2.1 Charge Transfer with the Dendritic Box 31 2.2.2 Photosensitizer in the Dendritic Box 35 2.2.3 Concluding Remarks 40 2.3 Perforated Dendritic Box 40 2.3.1 Preparation ofDAB-dendr-(NH-t-BOC-Gly)n 41 2.3.2 Hydrogen Bonding in Solid State 43 2.3.3 Hydrogen Bonding in Solution 44 2.3.4 Host-Guest Interaetions of DAB-dendr-(NH-t-BOC-Gly)64 versus DAB-dendr-(NH-t-BOC-L-Phe)a4 46 2.3.5 Concluding Remarks 48 2.4 Overall Conclusions 49 2.5 Experimental Section 50 2.6 Heferences and Notes 53 Chapter3 Nitroxyl-Functionalized Dendrimers 57 3.1 · Introduetion 58 3.2 Synthesis 59 3.3 EPR Spectroscopy 61 3.4 IR Speetroseopy 67 3.5 Influence of Spaeer Length on Biradieals 69 3.6 Condusion 71 3.7 Experimental Section 72 3.8 Referenees and Notes 73 Chapter4 Metallodendrimers 77 4.1 Introduetion 78 4.2 Poly(propylene imine) Dendrimers as Polyvalent Ligands 80 4.2.1 Cu(II)-eomplexes 80 4.2.2 Zn(II)-complexes 86 4.2.3 Ni(Il)-eomplexes 86 4.3 Catalysis 88 4.3.1 Azide-binding by Cu(Il)-dendrimers 88 4.3.2 Ester Hydrolysis with Zn(II)-dendrimers 89 4.4 Separation based on Nanoscopie Size 91 4.4.1 Nanofiltration 92 4.4.2 Metal Absorption 93 4.4.3 Reversible Azide-Binding 95 4.4.4 Ester Hydralysis in Membrane Reactor 96 4.5 Conclusions 98 4.6 Experimental Section 98 4.7 References and Notes 100 Chapter 5 Biomimicry with Dendrimers 105 5.1 Introduetion 106 5.2 Multi-Copper Hemocyanine Model 107 5.2.1 Synthesis and Metal-Binding Properties DAB-dendr-(PY2)n 108 5.2.2 Binding of Cu(l) and Û2 by DAB-dendr-(PY2)a2. 112 5.2.3 Concluding Remarks 114 5.3 Non-Covalent and Covalent Dendritic Multi-Porphyrin Arrays 114 5.3.1 Non-Covalent Multi-Porphyrin Assemblies 115 5.3.2 Covalent Multi-Porphyrin Assemblies 119 5.3.3 Concluding Remarks 123 5.4 Conclusions 123 5.5 Experimental Section 125 5.6 References and Notes 129 Summary 133 Samenvatting 135 Curriculum Vitae 137 List of Publications 139 Dankwoord 141 A bout Dendrimers* 1 Abstract: The esthetically appealing structures of dendrimers have attracted the interest {ram many different disciplines of science. In this chapter the literature on some controversial issues in dendrimer research is reviewed, aiming at an enhanced insight into the purity of dendrimers and their conformational behavior. The translation of dendrimer properties into functional materials, is the scope ofthe subsequent chapters. * Part ofthis work has been published: Bosman, A.W.; Janssen, H.M.; Meijer, E. W. Chem. Rev. 1999,99, xxxx. Chapter1 1.1 Introduetion Ideally, dendrimers are perfect monodisperse macromolecules with a regular and highly branched three-dimensional architecture. Dendrimers are produced in an iterative sequence of reaction steps, in which each additional iteration leads to a higher generation materiaL The first example of an iterative synthetic procedure towards well­ defined branched structures has been reported by Vögtle,1 who named thls procedure a "cascade synthesis". A few years later, in the early 1980s, Denkewalter patented the synthesis of 1-lysine-based dendrimers.2 The patents describe structures up to high generations, however, except for size exclusion chromatography (SEC) data,a no detailed characteristics of the materials are given. The first dendritic structures that have been thoroughly investigated and that have received widespread attention are Tomalia's PAMAM dendrimers4 and Newkome's "arborol" systems.5 Both dendrimers are constructed divergently, implying that the synthesis is started with a multifunctional core molecule and is elaborated to the periphery. At a later date and on the basis of the original work of Vögtle, 1 divergently produced poly(propylene imine) dendrimers have been reported by Mülhaupt6 and de Brabander.7 Today, these poly(propylene imine) dendrimers are commercially available. In 1990, Fréchet introduced the convergent approach towards dendrimers.s In convergent procedures, the synthesis is started at the periphery and elaborated to the core. Fréchet's aromatic polyether dendrimers are easily accessible and have been studied frequently, not only by the Fréchet group but also by other researchers. Finally, Moore's convergently produced phenylacetylene dendrimersll-11 are the last of the five classes of dendrimers, reported up to high generations, that are studied in detail and most known. Additionally, many other types of interesting, valuable, and esthetically pleasing dendritic systems have been developed, 12 and thus, a variety of dendritic scaffolds has beoome accessible with defined nanoscopic dimensions and discrete numbers offunctional end groups. Many of the intriguing properties of dendrimers as well as their syntheses and possible applications are discussed in excellent hooks and reviews that have been publisbed by various experts in the field.12-19 In this chapter, studies are highlighted that contribute to a better understanding of the properties of dendrimers and studies that offer insight into the possibilities for and the limitations of the use of dendritic materials. Some of these studies relate to three somewhat controversial issues. First, one can question the perfection of higher generation dendrimers. In the divergent synthetic approach, for example, several hundred reaction steps have to be conducted on the same molecular fragment to obtain higher generation species. Second, the conformational behavior of dendrimers is an issue of debate, giving rise to the following 2 About Dendrlmers questions: Are the end groups in dendrimers pointing outward or are they severely backfolded? Do dendrimers always have a globular shape or can this shape he highly distorted? Are cavities present inside the dendrimer? Is it possible to obtain site isolation in the core? How do the physical properties of dendrimers change at higher generations and how do these physical properties relate to those oflinear analogues? 1.2 The Purity of Dendrimers Two conceptually different synthetic approaches for the construction of high­ generation dendrimers exist: the divergent approach and the convergent approach.
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