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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


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A pseudorotaxane formed from a cucurbit[7]uril wheel and a bioinspired molecular axle with pH, light and redox-responsive properties

André Seco
  • Laboratório Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal
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/ Ana Marta Diniz
  • Health Technology College of Lisbon (ESTeSL) – Polytechnic Institute of Lisbon, 1990-096 Lisbon, Portugal
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/ João Sarrato
  • Laboratório Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal
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/ Henrique Mourão
  • Laboratório Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal
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/ Hugo Cruz
  • Laboratório Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal
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  • Laboratório Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal
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/ Nuno Basílio
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  • Laboratório Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516 Caparica, Portugal
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Published Online: 2019-10-25 | DOI: https://doi.org/10.1515/pac-2019-0225

Abstract

A pH-, light- and redox-responsive flavylium-bipyridinium molecular dyad (bioinspired in natural anthocyanins) was synthesized and employed to devise a pseudorotaxane with the macrocycle cucurbit[7]uril (CB7) in aqueous solution. The inclusion complex was characterized by UV-Vis absorption, fluorescence emission, NMR and electrochemical techniques which demonstrate formation of a stable binary complex between the dyad and CB7 both under acidic and neutral conditions. It is noteworthy that the flavylium-bipyridinium tricationic dyad is only stable in highly acidic media, undergoing a reversible hydration reaction at slightly acidic or neutral pH to give a trans-chalcone-bipyridinium dication. 1H NMR experiments showed that in this last species the CB7 binds to the bipyridinium unit while in the tricationic species the macrocycle is positioned between the flavylium and the bipyridinium moieties. The different location of the CB7 wheel in the two dyad states allows control of the shuttling movement using light and pH stimuli that trigger the interconversion between these two species.

This article offers supplementary material which is provided at the end of the article.

Keywords: flavylium photoswitches; molecular machines; NICE-2018; photochemistry; supramolecular chemistry

Article note

A collection of invited papers based on presentations at the 4th International Conference on Bioinspired and Biobased Chemistry & Materials (NICE-2018), Nice, France, 14–17 October 2018.

References

About the article

Published Online: 2019-10-25


Funding Source: H2020-MSCA-RISE-2016

Award identifier / Grant number: 734834

This work was supported by LAQV-REQUIMTE, which is financed by the Portuguese FCT/MCTES (UID/QUI/50006/2019) and co-financed by the ERDF under the PT2020 (POCI-01-0145-FEDER-007265). FCT/MCTES is also acknowledged for supporting the National Portuguese NMR Network (RECI/BBB-BQB/0230/2012), projects PTDC/QUI-COL/32351/2017, PTDC/QUI-QFI/30951/2017 and CEECIND/00466/2017 (N.B.) (Funder Id: http://dx.doi.org/10.13039/501100001871). EC is acknowledged for the INFUSION project grant no. 734834 under H2020-MSCA-RISE-2016 (Funder Id: http://dx.doi.org/10.13039/100010665). H.C. acknowledges postdoctoral grant SFRH/BPD/102705/2014.


Citation Information: Pure and Applied Chemistry, 20190225, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2019-0225.

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