A Dynamic and Responsive Host in Action: Light-Controlled Molecular Encapsulation

Seán T.J. Ryan; Jesús del Barrio; Reynier Suardíaz; Daniel F. Ryan; Edina Rosta; Oren A. Scherman

doi:10.1002/anie.201607693

A Dynamic and Responsive Host in Action: Light-Controlled Molecular Encapsulation

Seán T.J. Ryan, Jesús del Barrio^*, Reynier Suardíaz, Daniel F. Ryan, Edina Rosta, Oren A. Scherman

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

The rational design of a flexible molecular box, oAzoBox⁴⁺, incoporating both photochromic and supramolecular recognition motifs is described. We exploit the E↔Z photoisomerization properties of azobenzenes to alter the shape of the cavity of the macrocycle upon absorption of light. Imidazolium motifs are used as hydrogen-bonding donor components, allowing for sequestration of small molecule guests in acetonitrile. Upon E→Z photoisomerization of oAzoBox⁴⁺ the guest is expelled from the macrocyclic cavity.

Original language	English
Pages (from-to)	16096-16100
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	52
Early online date	28 Oct 2016
DOIs	https://doi.org/10.1002/anie.201607693
Publication status	Published - 23 Dec 2016

Keywords

host–guest systems
hydrogen bonds
macrocycles
photochemistry
supramolecular chemistry

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title = "A Dynamic and Responsive Host in Action: Light-Controlled Molecular Encapsulation",

abstract = "The rational design of a flexible molecular box, oAzoBox4+, incoporating both photochromic and supramolecular recognition motifs is described. We exploit the E↔Z photoisomerization properties of azobenzenes to alter the shape of the cavity of the macrocycle upon absorption of light. Imidazolium motifs are used as hydrogen-bonding donor components, allowing for sequestration of small molecule guests in acetonitrile. Upon E→Z photoisomerization of oAzoBox4+ the guest is expelled from the macrocyclic cavity.",

keywords = "host–guest systems, hydrogen bonds, macrocycles, photochemistry, supramolecular chemistry",

author = "Ryan, \{Se{\'a}n T.J.\} and \{del Barrio\}, Jes{\'u}s and Reynier Suard{\'i}az and Ryan, \{Daniel F.\} and Edina Rosta and Scherman, \{Oren A.\}",

year = "2016",

month = dec,

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doi = "10.1002/anie.201607693",

language = "English",

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pages = "16096--16100",

journal = "Angewandte Chemie - International Edition",

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T1 - A Dynamic and Responsive Host in Action

T2 - Light-Controlled Molecular Encapsulation

AU - Ryan, Seán T.J.

AU - del Barrio, Jesús

AU - Suardíaz, Reynier

AU - Ryan, Daniel F.

AU - Rosta, Edina

AU - Scherman, Oren A.

PY - 2016/12/23

Y1 - 2016/12/23

N2 - The rational design of a flexible molecular box, oAzoBox4+, incoporating both photochromic and supramolecular recognition motifs is described. We exploit the E↔Z photoisomerization properties of azobenzenes to alter the shape of the cavity of the macrocycle upon absorption of light. Imidazolium motifs are used as hydrogen-bonding donor components, allowing for sequestration of small molecule guests in acetonitrile. Upon E→Z photoisomerization of oAzoBox4+ the guest is expelled from the macrocyclic cavity.

AB - The rational design of a flexible molecular box, oAzoBox4+, incoporating both photochromic and supramolecular recognition motifs is described. We exploit the E↔Z photoisomerization properties of azobenzenes to alter the shape of the cavity of the macrocycle upon absorption of light. Imidazolium motifs are used as hydrogen-bonding donor components, allowing for sequestration of small molecule guests in acetonitrile. Upon E→Z photoisomerization of oAzoBox4+ the guest is expelled from the macrocyclic cavity.

KW - host–guest systems

KW - hydrogen bonds

KW - macrocycles

KW - photochemistry

KW - supramolecular chemistry

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U2 - 10.1002/anie.201607693

DO - 10.1002/anie.201607693

M3 - Article (Academic Journal)

C2 - 27791303

AN - SCOPUS:84995923598

SN - 1433-7851

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EP - 16100

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 52

ER -

A Dynamic and Responsive Host in Action: Light-Controlled Molecular Encapsulation

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