With the goal of understanding the electron transfer mechanism of fluorophore-functionalized pillar-arenes, a pillar[5]arene bearing two dansyl fluorophore moieties at the opposite rims of its cavity has been synthesized, and the behavior of such a new host molecule has been thoroughly investigated in the presence of an N,N'-di-(6-bromohexyl)-viologen derivative. H-1 NMR, NOESY and DOSY experiments demonstrated that the pillar[5]arene recognizes the viologen derivative, forming a 1:1 host-guest complex by including one of the two bromoalkyl chains within its pi-rich cavity. Photophysical and electrochemical studies revealed that, upon guest addition to the host, the fluorescence intensity of the complex is progressively quenched by a photoinduced electron transfer process (PET) from one of the dansyl groups of the host to the viologen moiety of the guest. (C) 2022 Elsevier Ltd. All rights reserved.

Photoinduced electron transfer in host-guest interactions of a viologen derivative with a didansyl-pillar[5]arene

A. Pappalardo;G. Trusso Sfrazzetto;A. Notti;F. Nastasi;G. Gattuso;
2022-01-01

Abstract

With the goal of understanding the electron transfer mechanism of fluorophore-functionalized pillar-arenes, a pillar[5]arene bearing two dansyl fluorophore moieties at the opposite rims of its cavity has been synthesized, and the behavior of such a new host molecule has been thoroughly investigated in the presence of an N,N'-di-(6-bromohexyl)-viologen derivative. H-1 NMR, NOESY and DOSY experiments demonstrated that the pillar[5]arene recognizes the viologen derivative, forming a 1:1 host-guest complex by including one of the two bromoalkyl chains within its pi-rich cavity. Photophysical and electrochemical studies revealed that, upon guest addition to the host, the fluorescence intensity of the complex is progressively quenched by a photoinduced electron transfer process (PET) from one of the dansyl groups of the host to the viologen moiety of the guest. (C) 2022 Elsevier Ltd. All rights reserved.
2022
Pillararenes
Viologen
Dansyl
Photoinduced electron transfer
DOSY NMR
Host-guest complexation
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11769/548099
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