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Modular supramolecular dimerization of optically tunable extended aryl viologens

Cucurbit[8]uril (CB[8]) mediated assembly of extended aryl viologens (EVs) into optically tunable dimers is reported for the first time. We show that the modular design and synthesis of a new class of π-conjugated viologen derivatives with rigid aromatic or heteroaromatic bridging units as well as e...

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Autores principales: Olesińska, Magdalena, Wu, Guanglu, Gómez-Coca, Silvia, Antón-García, Daniel, Szabó, Istvan, Rosta, Edina, Scherman, Oren A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6849629/
https://www.ncbi.nlm.nih.gov/pubmed/31803453
http://dx.doi.org/10.1039/c9sc03057c
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author Olesińska, Magdalena
Wu, Guanglu
Gómez-Coca, Silvia
Antón-García, Daniel
Szabó, Istvan
Rosta, Edina
Scherman, Oren A.
author_facet Olesińska, Magdalena
Wu, Guanglu
Gómez-Coca, Silvia
Antón-García, Daniel
Szabó, Istvan
Rosta, Edina
Scherman, Oren A.
author_sort Olesińska, Magdalena
collection PubMed
description Cucurbit[8]uril (CB[8]) mediated assembly of extended aryl viologens (EVs) into optically tunable dimers is reported for the first time. We show that the modular design and synthesis of a new class of π-conjugated viologen derivatives with rigid aromatic or heteroaromatic bridging units as well as electron donating molecular recognition motifs enable their self-assembly into 2 : 2 complexes with CB[8]. The quantitative dimerization process involving these two molecular components in an aqueous solution enables excimer-like interactions between closely packed charged guests giving rise to distinct spectroscopic behavior. The nature of these dimers (CB[8](2)·(EV[X]R)(2)) in the ground and excited states was characterized by NMR, isothermal titration calorimetry, and steady-state spectroscopic measurements.
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spelling pubmed-68496292019-12-04 Modular supramolecular dimerization of optically tunable extended aryl viologens Olesińska, Magdalena Wu, Guanglu Gómez-Coca, Silvia Antón-García, Daniel Szabó, Istvan Rosta, Edina Scherman, Oren A. Chem Sci Chemistry Cucurbit[8]uril (CB[8]) mediated assembly of extended aryl viologens (EVs) into optically tunable dimers is reported for the first time. We show that the modular design and synthesis of a new class of π-conjugated viologen derivatives with rigid aromatic or heteroaromatic bridging units as well as electron donating molecular recognition motifs enable their self-assembly into 2 : 2 complexes with CB[8]. The quantitative dimerization process involving these two molecular components in an aqueous solution enables excimer-like interactions between closely packed charged guests giving rise to distinct spectroscopic behavior. The nature of these dimers (CB[8](2)·(EV[X]R)(2)) in the ground and excited states was characterized by NMR, isothermal titration calorimetry, and steady-state spectroscopic measurements. Royal Society of Chemistry 2019-08-12 /pmc/articles/PMC6849629/ /pubmed/31803453 http://dx.doi.org/10.1039/c9sc03057c Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Olesińska, Magdalena
Wu, Guanglu
Gómez-Coca, Silvia
Antón-García, Daniel
Szabó, Istvan
Rosta, Edina
Scherman, Oren A.
Modular supramolecular dimerization of optically tunable extended aryl viologens
title Modular supramolecular dimerization of optically tunable extended aryl viologens
title_full Modular supramolecular dimerization of optically tunable extended aryl viologens
title_fullStr Modular supramolecular dimerization of optically tunable extended aryl viologens
title_full_unstemmed Modular supramolecular dimerization of optically tunable extended aryl viologens
title_short Modular supramolecular dimerization of optically tunable extended aryl viologens
title_sort modular supramolecular dimerization of optically tunable extended aryl viologens
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6849629/
https://www.ncbi.nlm.nih.gov/pubmed/31803453
http://dx.doi.org/10.1039/c9sc03057c
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