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Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane

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Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. / Kosikova, Tamara; Hassan, Nurul Izzaty Binti; Cordes, David Bradford; Slawin, Alexandra Martha Zoya; Philp, Douglas.

In: Journal of the American Chemical Society, Vol. 137, No. 51, 30.12.2015, p. 16074–16083.

Research output: Contribution to journalArticle

Harvard

Kosikova, T, Hassan, NIB, Cordes, DB, Slawin, AMZ & Philp, D 2015, 'Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane', Journal of the American Chemical Society, vol. 137, no. 51, pp. 16074–16083. https://doi.org/10.1021/jacs.5b09738

APA

Kosikova, T., Hassan, N. I. B., Cordes, D. B., Slawin, A. M. Z., & Philp, D. (2015). Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. Journal of the American Chemical Society, 137(51), 16074–16083. https://doi.org/10.1021/jacs.5b09738

Vancouver

Kosikova T, Hassan NIB, Cordes DB, Slawin AMZ, Philp D. Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. Journal of the American Chemical Society. 2015 Dec 30;137(51):16074–16083. https://doi.org/10.1021/jacs.5b09738

Author

Kosikova, Tamara ; Hassan, Nurul Izzaty Binti ; Cordes, David Bradford ; Slawin, Alexandra Martha Zoya ; Philp, Douglas. / Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. In: Journal of the American Chemical Society. 2015 ; Vol. 137, No. 51. pp. 16074–16083.

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@article{1be9a342ebb542a1838e6afed8381e6c,
title = "Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane",
abstract = "Within a small interconnected reaction network, orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. Rotaxane formation is governed by a central, hydrogen bonding-mediated binding equilibrium between a macrocycle and a linear component, which associate to give a reactive pseudorotaxane. Both the pseudorotaxane and the linear component undergo irreversible, recognition-mediated 1,3-dipolar cycloaddition reactions with a stoppering maleimide group, forming rotaxane and thread, respectively. As a result of these orthogonal recognition-mediated processes, the rotaxane and thread can act as autocatalytic templates for their own formation and also operate as crosscatalytic templates for each other. However, the interplay between the recognition and reaction processes in this reaction network results in the formation of undesirable pseudorotaxane complexes, causing thread formation to exceed rotaxane formation in the current experimental system. Nevertheless, in the absence of competitive macrocycle-binding sites, realization of a replicating network favoring formation of rotaxane is possible.",
author = "Tamara Kosikova and Hassan, {Nurul Izzaty Binti} and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and Douglas Philp",
note = "The financial support for this work was provided by EPSRC (Grant EP/K503162/1 and EP/E017851/1) and the Ministry for Higher Education Malaysia.",
year = "2015",
month = "12",
day = "30",
doi = "10.1021/jacs.5b09738",
language = "English",
volume = "137",
pages = "16074–16083",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "AMER CHEMICAL SOC",
number = "51",

}

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TY - JOUR

T1 - Orthogonal recognition processes drive the assembly and replication of a [2]rotaxane

AU - Kosikova, Tamara

AU - Hassan, Nurul Izzaty Binti

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Philp, Douglas

N1 - The financial support for this work was provided by EPSRC (Grant EP/K503162/1 and EP/E017851/1) and the Ministry for Higher Education Malaysia.

PY - 2015/12/30

Y1 - 2015/12/30

N2 - Within a small interconnected reaction network, orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. Rotaxane formation is governed by a central, hydrogen bonding-mediated binding equilibrium between a macrocycle and a linear component, which associate to give a reactive pseudorotaxane. Both the pseudorotaxane and the linear component undergo irreversible, recognition-mediated 1,3-dipolar cycloaddition reactions with a stoppering maleimide group, forming rotaxane and thread, respectively. As a result of these orthogonal recognition-mediated processes, the rotaxane and thread can act as autocatalytic templates for their own formation and also operate as crosscatalytic templates for each other. However, the interplay between the recognition and reaction processes in this reaction network results in the formation of undesirable pseudorotaxane complexes, causing thread formation to exceed rotaxane formation in the current experimental system. Nevertheless, in the absence of competitive macrocycle-binding sites, realization of a replicating network favoring formation of rotaxane is possible.

AB - Within a small interconnected reaction network, orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. Rotaxane formation is governed by a central, hydrogen bonding-mediated binding equilibrium between a macrocycle and a linear component, which associate to give a reactive pseudorotaxane. Both the pseudorotaxane and the linear component undergo irreversible, recognition-mediated 1,3-dipolar cycloaddition reactions with a stoppering maleimide group, forming rotaxane and thread, respectively. As a result of these orthogonal recognition-mediated processes, the rotaxane and thread can act as autocatalytic templates for their own formation and also operate as crosscatalytic templates for each other. However, the interplay between the recognition and reaction processes in this reaction network results in the formation of undesirable pseudorotaxane complexes, causing thread formation to exceed rotaxane formation in the current experimental system. Nevertheless, in the absence of competitive macrocycle-binding sites, realization of a replicating network favoring formation of rotaxane is possible.

UR - http://pubs.acs.org/doi/suppl/10.1021/jacs.5b09738

U2 - 10.1021/jacs.5b09738

DO - 10.1021/jacs.5b09738

M3 - Article

VL - 137

SP - 16074

EP - 16083

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 51

ER -

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