Helical chirality in donor-acceptor catenanes

Scott A. Vignon; Jason Wong; Hsian Rong Tseng; J. Fraser Stoddart

doi:10.1021/ol0364881

Helical chirality in donor-acceptor catenanes

Scott A. Vignon^*, Jason Wong, Hsian Rong Tseng, J. Fraser Stoddart

^*Corresponding author for this work

Chemistry

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

60 Scopus citations

Abstract

A [2]catenane in which the macrocyclic polyether, bisparaphenylene[34] crown-10, is interlocked with the tetracationic cyclophane, cyclobis-(paraquat- p-phenylene), is shown by dynamic ¹H NMR spectroscopy, using (i) neutral and (ii) anionic chiral shift reagents (CSRs), to exist at low temperatures (197 K) in acetone-d₆ solutions as 1:1 and 2:1 mixtures of diastereoisomeric complexes and salts, respectively, as a consequence of the helical chirality associated with the [2]catenane interacting with the CSRs.

Original language	English (US)
Pages (from-to)	1095-1098
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	7
DOIs	https://doi.org/10.1021/ol0364881
State	Published - Apr 1 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Helical chirality in donor-acceptor catenanes",

abstract = "A [2]catenane in which the macrocyclic polyether, bisparaphenylene[34] crown-10, is interlocked with the tetracationic cyclophane, cyclobis-(paraquat- p-phenylene), is shown by dynamic 1H NMR spectroscopy, using (i) neutral and (ii) anionic chiral shift reagents (CSRs), to exist at low temperatures (197 K) in acetone-d6 solutions as 1:1 and 2:1 mixtures of diastereoisomeric complexes and salts, respectively, as a consequence of the helical chirality associated with the [2]catenane interacting with the CSRs.",

author = "Vignon, {Scott A.} and Jason Wong and Tseng, {Hsian Rong} and Stoddart, {J. Fraser}",

year = "2004",

month = apr,

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doi = "10.1021/ol0364881",

language = "English (US)",

volume = "6",

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journal = "Organic Letters",

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T1 - Helical chirality in donor-acceptor catenanes

AU - Vignon, Scott A.

AU - Wong, Jason

AU - Tseng, Hsian Rong

AU - Stoddart, J. Fraser

PY - 2004/4/1

Y1 - 2004/4/1

N2 - A [2]catenane in which the macrocyclic polyether, bisparaphenylene[34] crown-10, is interlocked with the tetracationic cyclophane, cyclobis-(paraquat- p-phenylene), is shown by dynamic 1H NMR spectroscopy, using (i) neutral and (ii) anionic chiral shift reagents (CSRs), to exist at low temperatures (197 K) in acetone-d6 solutions as 1:1 and 2:1 mixtures of diastereoisomeric complexes and salts, respectively, as a consequence of the helical chirality associated with the [2]catenane interacting with the CSRs.

AB - A [2]catenane in which the macrocyclic polyether, bisparaphenylene[34] crown-10, is interlocked with the tetracationic cyclophane, cyclobis-(paraquat- p-phenylene), is shown by dynamic 1H NMR spectroscopy, using (i) neutral and (ii) anionic chiral shift reagents (CSRs), to exist at low temperatures (197 K) in acetone-d6 solutions as 1:1 and 2:1 mixtures of diastereoisomeric complexes and salts, respectively, as a consequence of the helical chirality associated with the [2]catenane interacting with the CSRs.

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DO - 10.1021/ol0364881

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SP - 1095

EP - 1098

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Helical chirality in donor-acceptor catenanes

Abstract

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