Electron sharing and anion-π recognition in molecular triangular prisms

Severin T. Schneebeli; Marco Frasconi; Zhichang Liu; Yilei Wu; Daniel M. Gardner; Nathan L. Strutt; Chuyang Cheng; Raanan Carmieli; Michael R Wasielewski; J Fraser Stoddart

doi:10.1002/anie.201307984

Electron sharing and anion-π recognition in molecular triangular prisms

Severin T. Schneebeli, Marco Frasconi, Zhichang Liu, Yilei Wu, Daniel M. Gardner, Nathan L. Strutt, Chuyang Cheng, Raanan Carmieli, Michael R Wasielewski^*, J Fraser Stoddart

^*Corresponding author for this work

Chemistry

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

148 Scopus citations

Abstract

Stacking on a full belly: Triangular molecular prisms display electron sharing among their triangularly arranged naphthalenediimide (NDI) redox centers. Their electron-deficient cavities encapsulate linear triiodide anions, leading to the formation of supramolecular helices in the solid state. Chirality transfer is observed from the six chiral centers of the filled prisms to the single-handed helices.

Original language	English (US)
Pages (from-to)	13100-13104
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	49
DOIs	https://doi.org/10.1002/anie.201307984
State	Published - Dec 2 2013

Keywords

anion-π interactions
helical π-π stacking
macrocycles
mixed-valence compounds
radical anions

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201307984

Cite this

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title = "Electron sharing and anion-π recognition in molecular triangular prisms",

abstract = "Stacking on a full belly: Triangular molecular prisms display electron sharing among their triangularly arranged naphthalenediimide (NDI) redox centers. Their electron-deficient cavities encapsulate linear triiodide anions, leading to the formation of supramolecular helices in the solid state. Chirality transfer is observed from the six chiral centers of the filled prisms to the single-handed helices.",

keywords = "anion-π interactions, helical π-π stacking, macrocycles, mixed-valence compounds, radical anions",

author = "Schneebeli, {Severin T.} and Marco Frasconi and Zhichang Liu and Yilei Wu and Gardner, {Daniel M.} and Strutt, {Nathan L.} and Chuyang Cheng and Raanan Carmieli and Wasielewski, {Michael R} and Stoddart, {J Fraser}",

year = "2013",

month = dec,

day = "2",

doi = "10.1002/anie.201307984",

language = "English (US)",

volume = "52",

pages = "13100--13104",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

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TY - JOUR

T1 - Electron sharing and anion-π recognition in molecular triangular prisms

AU - Schneebeli, Severin T.

AU - Frasconi, Marco

AU - Liu, Zhichang

AU - Wu, Yilei

AU - Gardner, Daniel M.

AU - Strutt, Nathan L.

AU - Cheng, Chuyang

AU - Carmieli, Raanan

AU - Wasielewski, Michael R

AU - Stoddart, J Fraser

PY - 2013/12/2

Y1 - 2013/12/2

N2 - Stacking on a full belly: Triangular molecular prisms display electron sharing among their triangularly arranged naphthalenediimide (NDI) redox centers. Their electron-deficient cavities encapsulate linear triiodide anions, leading to the formation of supramolecular helices in the solid state. Chirality transfer is observed from the six chiral centers of the filled prisms to the single-handed helices.

AB - Stacking on a full belly: Triangular molecular prisms display electron sharing among their triangularly arranged naphthalenediimide (NDI) redox centers. Their electron-deficient cavities encapsulate linear triiodide anions, leading to the formation of supramolecular helices in the solid state. Chirality transfer is observed from the six chiral centers of the filled prisms to the single-handed helices.

KW - anion-π interactions

KW - helical π-π stacking

KW - macrocycles

KW - mixed-valence compounds

KW - radical anions

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U2 - 10.1002/anie.201307984

DO - 10.1002/anie.201307984

M3 - Article

C2 - 24227594

AN - SCOPUS:84888581674

SN - 1433-7851

VL - 52

SP - 13100

EP - 13104

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 49

ER -

Electron sharing and anion-π recognition in molecular triangular prisms

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 958572: Experimental Crystal Structure Determination

CCDC 958570: Experimental Crystal Structure Determination

CCDC 958571: Experimental Crystal Structure Determination

Cite this

Electron sharing and anion-π recognition in molecular triangular prisms

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 958572: Experimental Crystal Structure Determination

CCDC 958570: Experimental Crystal Structure Determination

CCDC 958571: Experimental Crystal Structure Determination

Cite this