Controlling association kinetics in the formation of donor-acceptor pseudorotaxanes

Paul R. McGonigal; Hao Li; Chuyang Cheng; Severin T. Schneebeli; Marco Frasconi; Leah S. Witus; J. Fraser Stoddart

doi:10.1016/j.tetlet.2015.01.169

Controlling association kinetics in the formation of donor-acceptor pseudorotaxanes

Paul R. McGonigal, Hao Li, Chuyang Cheng, Severin T. Schneebeli, Marco Frasconi, Leah S. Witus, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

17 Scopus citations

Abstract

Abstract We report a systematic investigation of size-complementary stoppering groups used to determine the kinetics of threading a cyclophane, namely cyclobis(paraquat-p-phenylene), onto a series of molecular dumbbells. We have identified a set of simple functionalized phenyl and biaryl groups that present activation energy barriers between 16.7 and 26.6 kcal mol^-1 to threading the dumbbells. These barriers will be employed as 'steric speed bumps' to modulate kinetics in artificial molecular pumps that operate based upon a delicate balance of noncovalent bonding interactions.

Original language	English (US)
Article number	45839
Pages (from-to)	3591-3594
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.169
State	Published - May 25 2015

Keywords

Cyclophane
Inclusion complex
Kinetics
Pseudorotaxane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.01.169

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title = "Controlling association kinetics in the formation of donor-acceptor pseudorotaxanes",

abstract = "Abstract We report a systematic investigation of size-complementary stoppering groups used to determine the kinetics of threading a cyclophane, namely cyclobis(paraquat-p-phenylene), onto a series of molecular dumbbells. We have identified a set of simple functionalized phenyl and biaryl groups that present activation energy barriers between 16.7 and 26.6 kcal mol-1 to threading the dumbbells. These barriers will be employed as 'steric speed bumps' to modulate kinetics in artificial molecular pumps that operate based upon a delicate balance of noncovalent bonding interactions.",

keywords = "Cyclophane, Inclusion complex, Kinetics, Pseudorotaxane",

author = "McGonigal, {Paul R.} and Hao Li and Chuyang Cheng and Schneebeli, {Severin T.} and Marco Frasconi and Witus, {Leah S.} and Stoddart, {J. Fraser}",

note = "Funding Information: This material is based on work supported by the National Science Foundation (NSF) under CHE-1308107. P.R.M. thanks the US–UK Fulbright Commission for an All-Disciplines Scholarship. S.T.S. and L.S.W. acknowledge support from the International Institute for Nanotechnology (IIN) at Northwestern University . Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = may,

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doi = "10.1016/j.tetlet.2015.01.169",

language = "English (US)",

volume = "56",

pages = "3591--3594",

journal = "Tetrahedron Letters",

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T1 - Controlling association kinetics in the formation of donor-acceptor pseudorotaxanes

AU - McGonigal, Paul R.

AU - Li, Hao

AU - Cheng, Chuyang

AU - Schneebeli, Severin T.

AU - Frasconi, Marco

AU - Witus, Leah S.

AU - Stoddart, J. Fraser

N1 - Funding Information: This material is based on work supported by the National Science Foundation (NSF) under CHE-1308107. P.R.M. thanks the US–UK Fulbright Commission for an All-Disciplines Scholarship. S.T.S. and L.S.W. acknowledge support from the International Institute for Nanotechnology (IIN) at Northwestern University . Publisher Copyright: © 2015 Elsevier Ltd.

PY - 2015/5/25

Y1 - 2015/5/25

N2 - Abstract We report a systematic investigation of size-complementary stoppering groups used to determine the kinetics of threading a cyclophane, namely cyclobis(paraquat-p-phenylene), onto a series of molecular dumbbells. We have identified a set of simple functionalized phenyl and biaryl groups that present activation energy barriers between 16.7 and 26.6 kcal mol-1 to threading the dumbbells. These barriers will be employed as 'steric speed bumps' to modulate kinetics in artificial molecular pumps that operate based upon a delicate balance of noncovalent bonding interactions.

AB - Abstract We report a systematic investigation of size-complementary stoppering groups used to determine the kinetics of threading a cyclophane, namely cyclobis(paraquat-p-phenylene), onto a series of molecular dumbbells. We have identified a set of simple functionalized phenyl and biaryl groups that present activation energy barriers between 16.7 and 26.6 kcal mol-1 to threading the dumbbells. These barriers will be employed as 'steric speed bumps' to modulate kinetics in artificial molecular pumps that operate based upon a delicate balance of noncovalent bonding interactions.

KW - Cyclophane

KW - Inclusion complex

KW - Kinetics

KW - Pseudorotaxane

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VL - 56

SP - 3591

EP - 3594

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

M1 - 45839

ER -

Controlling association kinetics in the formation of donor-acceptor pseudorotaxanes

Abstract

Keywords

ASJC Scopus subject areas

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