Competitive inclusion of molecular photo-switches in host cavities

He Huang; Alberto  Juan; Nathalie Katsonis; Jurriaan Huskens

doi:10.1016/j.tet.2017.05.026

Competitive inclusion of molecular photo-switches in host cavities

He Huang
, Alberto Juan
, Nathalie Katsonis
, Jurriaan Huskens^*

^*Corresponding author for this work

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

23 Citations (Scopus)

285 Downloads (Pure)

Abstract

Azobenzene is a widely used guest molecule to build up dynamic photo-responsive host-guest systems. Here, we studied the host-guest complexation of a water-soluble, ortho-fluorinated azobenzene with two different host molecules, a cyclodextrin (β-CD) and a cucurbit[8]uril (CB[8]), and demonstrate that in the presence of both, the guest forms two stable supramolecular complexes selectively. In its trans-form, it favors binding to β-CD, whereas in its cis-form it favors complexation to CB[8]. Upon light-triggered photo-isomerization, the photoswitch was reversibly and selectively transferred from one host cavity to the other. This light-driven host exchange provides a new tool for supramolecular systems.

Original language	English
Pages (from-to)	4913-4917
Number of pages	5
Journal	Tetrahedron
Volume	73
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2017.05.026
Publication status	Published - 17 Aug 2017

Keywords

Dynamic molecular systems
Photochromic switches
Supramolecular chemistry

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10.1016/j.tet.2017.05.026

ArticleFinal published version, 912 KBLicence: CC BY

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title = "Competitive inclusion of molecular photo-switches in host cavities",

abstract = "Azobenzene is a widely used guest molecule to build up dynamic photo-responsive host-guest systems. Here, we studied the host-guest complexation of a water-soluble, ortho-fluorinated azobenzene with two different host molecules, a cyclodextrin (β-CD) and a cucurbit[8]uril (CB[8]), and demonstrate that in the presence of both, the guest forms two stable supramolecular complexes selectively. In its trans-form, it favors binding to β-CD, whereas in its cis-form it favors complexation to CB[8]. Upon light-triggered photo-isomerization, the photoswitch was reversibly and selectively transferred from one host cavity to the other. This light-driven host exchange provides a new tool for supramolecular systems.",

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AU - Huang, He

AU - Juan, Alberto

AU - Katsonis, Nathalie

AU - Huskens, Jurriaan

PY - 2017/8/17

Y1 - 2017/8/17

N2 - Azobenzene is a widely used guest molecule to build up dynamic photo-responsive host-guest systems. Here, we studied the host-guest complexation of a water-soluble, ortho-fluorinated azobenzene with two different host molecules, a cyclodextrin (β-CD) and a cucurbit[8]uril (CB[8]), and demonstrate that in the presence of both, the guest forms two stable supramolecular complexes selectively. In its trans-form, it favors binding to β-CD, whereas in its cis-form it favors complexation to CB[8]. Upon light-triggered photo-isomerization, the photoswitch was reversibly and selectively transferred from one host cavity to the other. This light-driven host exchange provides a new tool for supramolecular systems.

AB - Azobenzene is a widely used guest molecule to build up dynamic photo-responsive host-guest systems. Here, we studied the host-guest complexation of a water-soluble, ortho-fluorinated azobenzene with two different host molecules, a cyclodextrin (β-CD) and a cucurbit[8]uril (CB[8]), and demonstrate that in the presence of both, the guest forms two stable supramolecular complexes selectively. In its trans-form, it favors binding to β-CD, whereas in its cis-form it favors complexation to CB[8]. Upon light-triggered photo-isomerization, the photoswitch was reversibly and selectively transferred from one host cavity to the other. This light-driven host exchange provides a new tool for supramolecular systems.

KW - Dynamic molecular systems

KW - Photochromic switches

KW - Supramolecular chemistry

UR - https://www.scopus.com/pages/publications/85019434390

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DO - 10.1016/j.tet.2017.05.026

M3 - Article

AN - SCOPUS:85019434390

SN - 0040-4020

VL - 73

SP - 4913

EP - 4917

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Competitive inclusion of molecular photo-switches in host cavities

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