Threading-gated photochromism in [2]pseudorotaxanes

Threading-gated photochromism in [2]pseudorotaxanes

Rigid, Y-shaped imidazole compounds containing the bis(thienyl)ethene moiety were designed and synthesized. The 4,5-bis(benzothienyl)-2-phenylimidazolium cations were then used as axles for [2]pseudorotaxane formation with 24-membered crown ether wheels. It was demonstrated using 1 H NMR spectroscop...

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Veröffentlicht in:Chemical science (Cambridge) 2019-05, Vol.1 (19), p.514-5113
Hauptverfasser: Baggi, Giorgio, Casimiro, Lorenzo, Baroncini, Massimo, Silvi, Serena, Credi, Alberto, Loeb, Stephen J
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container_issue 19
container_start_page 514
container_title Chemical science (Cambridge)
container_volume 1
creator Baggi, Giorgio
Casimiro, Lorenzo
Baroncini, Massimo
Silvi, Serena
Credi, Alberto
Loeb, Stephen J
description Rigid, Y-shaped imidazole compounds containing the bis(thienyl)ethene moiety were designed and synthesized. The 4,5-bis(benzothienyl)-2-phenylimidazolium cations were then used as axles for [2]pseudorotaxane formation with 24-membered crown ether wheels. It was demonstrated using 1 H NMR spectroscopy, UV-Vis absorption and emission spectroscopies that this host-guest interaction results in significant changes in the photochromic properties of the imidazolium axles. This is a rare example of gated photochromism, which exploits the recognition event of an interpenetrated molecular system to tune the photochromic properties in one of the components. Photochromic axles bearing a bis(thienyl)ethene moiety exhibit threading-gated photochromism, where formation of a [2]pseudorotaxane with crown ether rings significantly enhances the photochromic properties of the axles.
doi_str_mv 10.1039/c9sc00913b
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title Threading-gated photochromism in [2]pseudorotaxanes
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