Design and synthesis of readily degradable acyloxysilane dendrimers

Christopher M. Downing; Michael N. Missaghi; Mayfair C. Kung; Harold H. Kung

doi:10.1016/j.tet.2011.07.068

Design and synthesis of readily degradable acyloxysilane dendrimers

Christopher M. Downing, Michael N. Missaghi, Mayfair C. Kung, Harold H. Kung^*

^*Corresponding author for this work

Chemical and Biological Engineering

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

10 Scopus citations

Abstract

Two types of dendrimers with AB₂ branching, one with acyloxysilanes at the branching position (V type) and the other at the non-branching position (Y type), were synthesized using hydrosilylation with chlorosilanes followed by heterofunctional condensation with olefin-functional carboxylic acids, and examined as readily degradable template materials. The V type dendrimer was much more susceptible to ligand redistribution with chlorosilanes during preparation, whereas the Y type was less. The acyloxysilane linkages in these dendrimers could be cleaved readily by alcoholysis or hydrolysis on demand, making for suitable templates.

Original language	English (US)
Pages (from-to)	7502-7509
Number of pages	8
Journal	Tetrahedron
Volume	67
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2011.07.068
State	Published - Sep 30 2011

Funding

We thank the U.S. Department of Energy , grant DE-FG02-03ER15457 , for support for CMD though the Institute for Catalysis in Energy Processes (ICEP) at Northwestern University, and grant DE-FG02-01ER15184 for support of MNM. We thank the Integrated Molecular Structure Characterization Education and Research Center (IMSERC) at Northwestern University for NMR facilities.

Keywords

Acyloxysilane
Degradable dendrimer
Ligand redistribution

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.07.068

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title = "Design and synthesis of readily degradable acyloxysilane dendrimers",

abstract = "Two types of dendrimers with AB2 branching, one with acyloxysilanes at the branching position (V type) and the other at the non-branching position (Y type), were synthesized using hydrosilylation with chlorosilanes followed by heterofunctional condensation with olefin-functional carboxylic acids, and examined as readily degradable template materials. The V type dendrimer was much more susceptible to ligand redistribution with chlorosilanes during preparation, whereas the Y type was less. The acyloxysilane linkages in these dendrimers could be cleaved readily by alcoholysis or hydrolysis on demand, making for suitable templates.",

keywords = "Acyloxysilane, Degradable dendrimer, Ligand redistribution",

author = "Downing, {Christopher M.} and Missaghi, {Michael N.} and Kung, {Mayfair C.} and Kung, {Harold H.}",

note = "Funding Information: We thank the U.S. Department of Energy , grant DE-FG02-03ER15457 , for support for CMD though the Institute for Catalysis in Energy Processes (ICEP) at Northwestern University, and grant DE-FG02-01ER15184 for support of MNM. We thank the Integrated Molecular Structure Characterization Education and Research Center (IMSERC) at Northwestern University for NMR facilities. ",

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T1 - Design and synthesis of readily degradable acyloxysilane dendrimers

AU - Downing, Christopher M.

AU - Missaghi, Michael N.

AU - Kung, Mayfair C.

AU - Kung, Harold H.

N1 - Funding Information: We thank the U.S. Department of Energy , grant DE-FG02-03ER15457 , for support for CMD though the Institute for Catalysis in Energy Processes (ICEP) at Northwestern University, and grant DE-FG02-01ER15184 for support of MNM. We thank the Integrated Molecular Structure Characterization Education and Research Center (IMSERC) at Northwestern University for NMR facilities.

PY - 2011/9/30

Y1 - 2011/9/30

N2 - Two types of dendrimers with AB2 branching, one with acyloxysilanes at the branching position (V type) and the other at the non-branching position (Y type), were synthesized using hydrosilylation with chlorosilanes followed by heterofunctional condensation with olefin-functional carboxylic acids, and examined as readily degradable template materials. The V type dendrimer was much more susceptible to ligand redistribution with chlorosilanes during preparation, whereas the Y type was less. The acyloxysilane linkages in these dendrimers could be cleaved readily by alcoholysis or hydrolysis on demand, making for suitable templates.

AB - Two types of dendrimers with AB2 branching, one with acyloxysilanes at the branching position (V type) and the other at the non-branching position (Y type), were synthesized using hydrosilylation with chlorosilanes followed by heterofunctional condensation with olefin-functional carboxylic acids, and examined as readily degradable template materials. The V type dendrimer was much more susceptible to ligand redistribution with chlorosilanes during preparation, whereas the Y type was less. The acyloxysilane linkages in these dendrimers could be cleaved readily by alcoholysis or hydrolysis on demand, making for suitable templates.

KW - Acyloxysilane

KW - Degradable dendrimer

KW - Ligand redistribution

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JO - Tetrahedron

JF - Tetrahedron

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Design and synthesis of readily degradable acyloxysilane dendrimers

Abstract

Funding

Keywords

ASJC Scopus subject areas

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