One-Pot Synthesis of Hyperbranched Polyethers

K. E. Uhrich; C. J. Hawker; J. M.J. Fréchet; S. R. Turner

doi:10.1021/ma00044a019

One-Pot Synthesis of Hyperbranched Polyethers

K. E. Uhrich, C. J. Hawker, J. M.J. Fréchet^*, S. R. Turner

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

256 Scopus citations

Abstract

A one-pot synthesis of a hyperbranched polyether using a A₂B type monomer under mild conditions is described. The monomer, 5-(bromomethyl)-1,3-dihydroxybenzene, undergoes self-condensation in the presence of potassium carbonate and 18-crown-6 to give polymers with weight-average molecular weights exceeding 10⁵. Spectroscopic analysis of the hyperbranched polymers reveals that both O-alkylation and C-alkylation occurs during polymerization. The polymers contain a large number of phenolic hydroxyl groups located both at chain ends and at monomer units involved in irregular growth. The phenolic groups of the hyperbranched polyethers can be modified readily and completely by simple acylation, benzylation, or silylation processes. Comparison of the size-exclusion chromatography data with absolute molecular weight measurements by low-angle laser light scattering supports the proposed hyperbranched structure of the polyethers.

Original language	English (US)
Pages (from-to)	4583-4587
Number of pages	5
Journal	Macromolecules
Volume	25
Issue number	18
DOIs	https://doi.org/10.1021/ma00044a019
State	Published - Aug 1 1992
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "One-Pot Synthesis of Hyperbranched Polyethers",

abstract = "A one-pot synthesis of a hyperbranched polyether using a A2B type monomer under mild conditions is described. The monomer, 5-(bromomethyl)-1,3-dihydroxybenzene, undergoes self-condensation in the presence of potassium carbonate and 18-crown-6 to give polymers with weight-average molecular weights exceeding 105. Spectroscopic analysis of the hyperbranched polymers reveals that both O-alkylation and C-alkylation occurs during polymerization. The polymers contain a large number of phenolic hydroxyl groups located both at chain ends and at monomer units involved in irregular growth. The phenolic groups of the hyperbranched polyethers can be modified readily and completely by simple acylation, benzylation, or silylation processes. Comparison of the size-exclusion chromatography data with absolute molecular weight measurements by low-angle laser light scattering supports the proposed hyperbranched structure of the polyethers.",

author = "Uhrich, {K. E.} and Hawker, {C. J.} and Fr{\'e}chet, {J. M.J.} and Turner, {S. R.}",

year = "1992",

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doi = "10.1021/ma00044a019",

language = "English (US)",

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journal = "Macromolecules",

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TY - JOUR

T1 - One-Pot Synthesis of Hyperbranched Polyethers

AU - Uhrich, K. E.

AU - Hawker, C. J.

AU - Fréchet, J. M.J.

AU - Turner, S. R.

PY - 1992/8/1

Y1 - 1992/8/1

N2 - A one-pot synthesis of a hyperbranched polyether using a A2B type monomer under mild conditions is described. The monomer, 5-(bromomethyl)-1,3-dihydroxybenzene, undergoes self-condensation in the presence of potassium carbonate and 18-crown-6 to give polymers with weight-average molecular weights exceeding 105. Spectroscopic analysis of the hyperbranched polymers reveals that both O-alkylation and C-alkylation occurs during polymerization. The polymers contain a large number of phenolic hydroxyl groups located both at chain ends and at monomer units involved in irregular growth. The phenolic groups of the hyperbranched polyethers can be modified readily and completely by simple acylation, benzylation, or silylation processes. Comparison of the size-exclusion chromatography data with absolute molecular weight measurements by low-angle laser light scattering supports the proposed hyperbranched structure of the polyethers.

AB - A one-pot synthesis of a hyperbranched polyether using a A2B type monomer under mild conditions is described. The monomer, 5-(bromomethyl)-1,3-dihydroxybenzene, undergoes self-condensation in the presence of potassium carbonate and 18-crown-6 to give polymers with weight-average molecular weights exceeding 105. Spectroscopic analysis of the hyperbranched polymers reveals that both O-alkylation and C-alkylation occurs during polymerization. The polymers contain a large number of phenolic hydroxyl groups located both at chain ends and at monomer units involved in irregular growth. The phenolic groups of the hyperbranched polyethers can be modified readily and completely by simple acylation, benzylation, or silylation processes. Comparison of the size-exclusion chromatography data with absolute molecular weight measurements by low-angle laser light scattering supports the proposed hyperbranched structure of the polyethers.

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U2 - 10.1021/ma00044a019

DO - 10.1021/ma00044a019

M3 - Article

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SP - 4583

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JO - Macromolecules

JF - Macromolecules

IS - 18

ER -

One-Pot Synthesis of Hyperbranched Polyethers

Abstract

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