Modular synthesis of bipyridinium oligomers and corresponding donor-acceptor oligorotaxanes with crown ethers

Chris M. Gothard; Carson J. Bruns; Nosheen A. Gothard; Bartosz A. Grzybowski; J. Fraser Stoddart

doi:10.1021/ol302301r

Modular synthesis of bipyridinium oligomers and corresponding donor-acceptor oligorotaxanes with crown ethers

Chris M. Gothard, Carson J. Bruns, Nosheen A. Gothard, Bartosz A. Grzybowski, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

21 Scopus citations

Abstract

Donor-acceptor [4]- and [6]rotaxanes have been prepared from bipyridinium (BIPY ²⁺) oligomers and 1,5-dinaphtho[38]crown-10 (DN38C10) by a threading-followed-by-stoppering protocol employing click chemistry. An efficient, straightforward route to the BIPY ²⁺ oligomers has been developed that requires little to no chromatographic purification. Unlike most donor-acceptor oligorotaxanes that have been reported to date, 100% of the recognition sites on the dumbbells are occupied by rings.

Original language	English (US)
Pages (from-to)	5066-5069
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	19
DOIs	https://doi.org/10.1021/ol302301r
State	Published - Oct 5 2012

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol302301r

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title = "Modular synthesis of bipyridinium oligomers and corresponding donor-acceptor oligorotaxanes with crown ethers",

abstract = "Donor-acceptor [4]- and [6]rotaxanes have been prepared from bipyridinium (BIPY 2+) oligomers and 1,5-dinaphtho[38]crown-10 (DN38C10) by a threading-followed-by-stoppering protocol employing click chemistry. An efficient, straightforward route to the BIPY 2+ oligomers has been developed that requires little to no chromatographic purification. Unlike most donor-acceptor oligorotaxanes that have been reported to date, 100% of the recognition sites on the dumbbells are occupied by rings.",

author = "Gothard, {Chris M.} and Bruns, {Carson J.} and Gothard, {Nosheen A.} and Grzybowski, {Bartosz A.} and Stoddart, {J. Fraser}",

year = "2012",

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doi = "10.1021/ol302301r",

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journal = "Organic Letters",

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T1 - Modular synthesis of bipyridinium oligomers and corresponding donor-acceptor oligorotaxanes with crown ethers

AU - Gothard, Chris M.

AU - Bruns, Carson J.

AU - Gothard, Nosheen A.

AU - Grzybowski, Bartosz A.

AU - Stoddart, J. Fraser

PY - 2012/10/5

Y1 - 2012/10/5

N2 - Donor-acceptor [4]- and [6]rotaxanes have been prepared from bipyridinium (BIPY 2+) oligomers and 1,5-dinaphtho[38]crown-10 (DN38C10) by a threading-followed-by-stoppering protocol employing click chemistry. An efficient, straightforward route to the BIPY 2+ oligomers has been developed that requires little to no chromatographic purification. Unlike most donor-acceptor oligorotaxanes that have been reported to date, 100% of the recognition sites on the dumbbells are occupied by rings.

AB - Donor-acceptor [4]- and [6]rotaxanes have been prepared from bipyridinium (BIPY 2+) oligomers and 1,5-dinaphtho[38]crown-10 (DN38C10) by a threading-followed-by-stoppering protocol employing click chemistry. An efficient, straightforward route to the BIPY 2+ oligomers has been developed that requires little to no chromatographic purification. Unlike most donor-acceptor oligorotaxanes that have been reported to date, 100% of the recognition sites on the dumbbells are occupied by rings.

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Modular synthesis of bipyridinium oligomers and corresponding donor-acceptor oligorotaxanes with crown ethers

Abstract

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