Solid-phase approaches toward cyclic oligomers

David B. Shortell; Liam C. Palmer; James M. Tour

doi:10.1016/S0040-4020(01)00930-9

Solid-phase approaches toward cyclic oligomers

David B. Shortell, Liam C. Palmer, James M. Tour^*

^*Corresponding author for this work

CRN - Center for Regenerative Nanomedicine

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

9 Scopus citations

Abstract

Strategies were sought to effect cyclizations of oligo(m-phenylene ethynylene) by exploiting pseudo-high dilution effects on polymer supports. Using Pd/Cu-catalyzed coupling protocols, Merrifield's resin (1% crosslinked chloromethylated polystyrene) proved inadequate for site isolation; inter-site couplings ensued on the flexible support. Conversely, use of the Argopore resin, a more highly crosslinked polystyrene, inhibited inter-site interactions, and no identifiable final product could be separated from the resin. Spectroscopic and mass spectrometric methods indicated that the product from the Argopore resin might be a threaded catenane.

Original language	English (US)
Pages (from-to)	9055-9065
Number of pages	11
Journal	Tetrahedron
Volume	57
Issue number	44
DOIs	https://doi.org/10.1016/S0040-4020(01)00930-9
State	Published - Oct 29 2001

Funding

This work was funded by the National Science Foundation. The trimethylsilylacetylene was kindly provided by Dr I. Chester of the FAR Research Inc.

Keywords

Macrocycle
Pseudo-high dilution
Supramolecular

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)00930-9

Cite this

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title = "Solid-phase approaches toward cyclic oligomers",

abstract = "Strategies were sought to effect cyclizations of oligo(m-phenylene ethynylene) by exploiting pseudo-high dilution effects on polymer supports. Using Pd/Cu-catalyzed coupling protocols, Merrifield's resin (1% crosslinked chloromethylated polystyrene) proved inadequate for site isolation; inter-site couplings ensued on the flexible support. Conversely, use of the Argopore resin, a more highly crosslinked polystyrene, inhibited inter-site interactions, and no identifiable final product could be separated from the resin. Spectroscopic and mass spectrometric methods indicated that the product from the Argopore resin might be a threaded catenane.",

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author = "Shortell, {David B.} and Palmer, {Liam C.} and Tour, {James M.}",

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T1 - Solid-phase approaches toward cyclic oligomers

AU - Shortell, David B.

AU - Palmer, Liam C.

AU - Tour, James M.

N1 - Funding Information: This work was funded by the National Science Foundation. The trimethylsilylacetylene was kindly provided by Dr I. Chester of the FAR Research Inc.

PY - 2001/10/29

Y1 - 2001/10/29

N2 - Strategies were sought to effect cyclizations of oligo(m-phenylene ethynylene) by exploiting pseudo-high dilution effects on polymer supports. Using Pd/Cu-catalyzed coupling protocols, Merrifield's resin (1% crosslinked chloromethylated polystyrene) proved inadequate for site isolation; inter-site couplings ensued on the flexible support. Conversely, use of the Argopore resin, a more highly crosslinked polystyrene, inhibited inter-site interactions, and no identifiable final product could be separated from the resin. Spectroscopic and mass spectrometric methods indicated that the product from the Argopore resin might be a threaded catenane.

AB - Strategies were sought to effect cyclizations of oligo(m-phenylene ethynylene) by exploiting pseudo-high dilution effects on polymer supports. Using Pd/Cu-catalyzed coupling protocols, Merrifield's resin (1% crosslinked chloromethylated polystyrene) proved inadequate for site isolation; inter-site couplings ensued on the flexible support. Conversely, use of the Argopore resin, a more highly crosslinked polystyrene, inhibited inter-site interactions, and no identifiable final product could be separated from the resin. Spectroscopic and mass spectrometric methods indicated that the product from the Argopore resin might be a threaded catenane.

KW - Macrocycle

KW - Pseudo-high dilution

KW - Supramolecular

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JO - Tetrahedron

JF - Tetrahedron

IS - 44

ER -

Solid-phase approaches toward cyclic oligomers

Abstract

Funding

Keywords

ASJC Scopus subject areas

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