Molecular Meccano, 52. - Template-directed synthesis of a rotacatenane

David B. Amabilino; Peter R. Ashton; José A. Bravo; Françisco M. Raymo; J. Fraser Stoddart; Andrew J P White; David J. Williams

doi:10.1002/(sici)1099-0690(199906)1999:6<1295::aid-ejoc1295>3.0.co;2-z

Molecular Meccano, 52. - Template-directed synthesis of a rotacatenane

David B. Amabilino, Peter R. Ashton, José A. Bravo, Françisco M. Raymo, J. Fraser Stoddart^*, Andrew J P White, David J. Williams

^*Corresponding author for this work

Chemistry

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

33 Scopus citations

Abstract

A [2]catenane, able to bind π-electron-rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so-called rotacatenane - i.e., a molecule composed of a dumbbell-shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single-crystal X-ray analyses. Furthermore, some of the co-conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable- temperature ¹H-NMR spectroscopy.

Original language	English (US)
Pages (from-to)	1295-1302
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	6
DOIs	https://doi.org/10.1002/(sici)1099-0690(199906)1999:6<1295::aid-ejoc1295>3.0.co;2-z
State	Published - Jun 1999

Keywords

Catenanes
Mechanically interlocked molecules
Molecular recognition
Rotaxanes
Template-directed synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/(sici)1099-0690(199906)1999:6<1295::aid-ejoc1295>3.0.co;2-z

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@article{02886e52daf747c19dca3ab8454995cc,

title = "Molecular Meccano, 52. - Template-directed synthesis of a rotacatenane",

abstract = "A [2]catenane, able to bind π-electron-rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so-called rotacatenane - i.e., a molecule composed of a dumbbell-shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single-crystal X-ray analyses. Furthermore, some of the co-conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable- temperature 1H-NMR spectroscopy.",

keywords = "Catenanes, Mechanically interlocked molecules, Molecular recognition, Rotaxanes, Template-directed synthesis",

author = "Amabilino, {David B.} and Ashton, {Peter R.} and Bravo, {Jos{\'e} A.} and Raymo, {Fran{\c c}isco M.} and Stoddart, {J. Fraser} and White, {Andrew J P} and Williams, {David J.}",

year = "1999",

month = jun,

doi = "10.1002/(sici)1099-0690(199906)1999:6<1295::aid-ejoc1295>3.0.co;2-z",

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pages = "1295--1302",

journal = "European Journal of Organic Chemistry",

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AU - Amabilino, David B.

AU - Ashton, Peter R.

AU - Bravo, José A.

AU - Raymo, Françisco M.

AU - Stoddart, J. Fraser

AU - White, Andrew J P

AU - Williams, David J.

PY - 1999/6

Y1 - 1999/6

N2 - A [2]catenane, able to bind π-electron-rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so-called rotacatenane - i.e., a molecule composed of a dumbbell-shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single-crystal X-ray analyses. Furthermore, some of the co-conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable- temperature 1H-NMR spectroscopy.

AB - A [2]catenane, able to bind π-electron-rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so-called rotacatenane - i.e., a molecule composed of a dumbbell-shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single-crystal X-ray analyses. Furthermore, some of the co-conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable- temperature 1H-NMR spectroscopy.

KW - Catenanes

KW - Mechanically interlocked molecules

KW - Molecular recognition

KW - Rotaxanes

KW - Template-directed synthesis

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M3 - Article

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SN - 1434-193X

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EP - 1302

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 6

ER -

Molecular Meccano, 52. - Template-directed synthesis of a rotacatenane

Abstract

Keywords

ASJC Scopus subject areas

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