Noncovalent synthesis of supramolecular dendritic architectures in water

M.A.C. Broeren, J.G. Linhardt, H. Malda, B.F.M. Waal, de, R.M. Versteegen, J.T. Meijer, D.W.P.M. Lowik, J.C.M. van Hest, M.H.P. Genderen, van, E.W. Meijer

Research output: Contribution to journalArticleAcademicpeer-review

14 Citations (Scopus)

Abstract

Water-soluble guest-host complexes are prepared in a two-step process. For this a new, polydisperse ethylene glycol containing guest molecule is synthesized that is soluble in both chloroform and water. This guest is able to bind to urea-adamantyl-modified poly(propylene imine) dendrimers in chloroform in a noncovalent manner. When the chloroform is slowly evaporated and D2O is added, the hydrophobic dendrimer is solubilized in water. This is not possible when the hydrophobic dendrimer is directly added to the hydrophilic guests in water. When the unmodified poly(ethylene glycol) starting material is used, no solubilization occurs, and this indicates that the urea-acetic acid head group is necessary to solubilize the dendrimer. Approximately 26 guests are required for solubilization of the dendrimer. A lower number of guests results in aggregation and precipitation of the dendrimer. A monodisperse guest molecule has been used in NMR studies to show that the guest molecule binds with its acidic head group to the periphery of the dendrimer. This methodology opens the way to functional dendrimer aggregates in aqueous media.
Original languageEnglish
Pages (from-to)6431-6437
Number of pages7
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume43
Issue number24
DOIs
Publication statusPublished - 2005

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Dendrimers
Water
Chloroform
Chlorine compounds
Urea
Molecules
Ethylene Glycol
Ethylene glycol
Acetic acid
Acetic Acid
Polyethylene glycols
Polypropylenes
Agglomeration
Nuclear magnetic resonance

Cite this

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title = "Noncovalent synthesis of supramolecular dendritic architectures in water",
abstract = "Water-soluble guest-host complexes are prepared in a two-step process. For this a new, polydisperse ethylene glycol containing guest molecule is synthesized that is soluble in both chloroform and water. This guest is able to bind to urea-adamantyl-modified poly(propylene imine) dendrimers in chloroform in a noncovalent manner. When the chloroform is slowly evaporated and D2O is added, the hydrophobic dendrimer is solubilized in water. This is not possible when the hydrophobic dendrimer is directly added to the hydrophilic guests in water. When the unmodified poly(ethylene glycol) starting material is used, no solubilization occurs, and this indicates that the urea-acetic acid head group is necessary to solubilize the dendrimer. Approximately 26 guests are required for solubilization of the dendrimer. A lower number of guests results in aggregation and precipitation of the dendrimer. A monodisperse guest molecule has been used in NMR studies to show that the guest molecule binds with its acidic head group to the periphery of the dendrimer. This methodology opens the way to functional dendrimer aggregates in aqueous media.",
author = "M.A.C. Broeren and J.G. Linhardt and H. Malda and {Waal, de}, B.F.M. and R.M. Versteegen and J.T. Meijer and D.W.P.M. Lowik and {van Hest}, J.C.M. and {Genderen, van}, M.H.P. and E.W. Meijer",
year = "2005",
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volume = "43",
pages = "6431--6437",
journal = "Journal of Polymer Science, Part A: Polymer Chemistry",
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Noncovalent synthesis of supramolecular dendritic architectures in water. / Broeren, M.A.C.; Linhardt, J.G.; Malda, H.; Waal, de, B.F.M.; Versteegen, R.M.; Meijer, J.T.; Lowik, D.W.P.M.; van Hest, J.C.M.; Genderen, van, M.H.P.; Meijer, E.W.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 43, No. 24, 2005, p. 6431-6437.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Noncovalent synthesis of supramolecular dendritic architectures in water

AU - Broeren, M.A.C.

AU - Linhardt, J.G.

AU - Malda, H.

AU - Waal, de, B.F.M.

AU - Versteegen, R.M.

AU - Meijer, J.T.

AU - Lowik, D.W.P.M.

AU - van Hest, J.C.M.

AU - Genderen, van, M.H.P.

AU - Meijer, E.W.

PY - 2005

Y1 - 2005

N2 - Water-soluble guest-host complexes are prepared in a two-step process. For this a new, polydisperse ethylene glycol containing guest molecule is synthesized that is soluble in both chloroform and water. This guest is able to bind to urea-adamantyl-modified poly(propylene imine) dendrimers in chloroform in a noncovalent manner. When the chloroform is slowly evaporated and D2O is added, the hydrophobic dendrimer is solubilized in water. This is not possible when the hydrophobic dendrimer is directly added to the hydrophilic guests in water. When the unmodified poly(ethylene glycol) starting material is used, no solubilization occurs, and this indicates that the urea-acetic acid head group is necessary to solubilize the dendrimer. Approximately 26 guests are required for solubilization of the dendrimer. A lower number of guests results in aggregation and precipitation of the dendrimer. A monodisperse guest molecule has been used in NMR studies to show that the guest molecule binds with its acidic head group to the periphery of the dendrimer. This methodology opens the way to functional dendrimer aggregates in aqueous media.

AB - Water-soluble guest-host complexes are prepared in a two-step process. For this a new, polydisperse ethylene glycol containing guest molecule is synthesized that is soluble in both chloroform and water. This guest is able to bind to urea-adamantyl-modified poly(propylene imine) dendrimers in chloroform in a noncovalent manner. When the chloroform is slowly evaporated and D2O is added, the hydrophobic dendrimer is solubilized in water. This is not possible when the hydrophobic dendrimer is directly added to the hydrophilic guests in water. When the unmodified poly(ethylene glycol) starting material is used, no solubilization occurs, and this indicates that the urea-acetic acid head group is necessary to solubilize the dendrimer. Approximately 26 guests are required for solubilization of the dendrimer. A lower number of guests results in aggregation and precipitation of the dendrimer. A monodisperse guest molecule has been used in NMR studies to show that the guest molecule binds with its acidic head group to the periphery of the dendrimer. This methodology opens the way to functional dendrimer aggregates in aqueous media.

U2 - 10.1002/pola.21068

DO - 10.1002/pola.21068

M3 - Article

VL - 43

SP - 6431

EP - 6437

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

SN - 0887-624X

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ER -