Modular supramolecular dimerization of optically tunable extended aryl viologens

Magdalena Olesińska; Guanglu Wu; Silvia Gómez-Coca; Daniel Antón-García; Istvan Szabó; Edina Rosta; Oren A. Scherman

doi:10.1039/c9sc03057c

Modular supramolecular dimerization of optically tunable extended aryl viologens

Magdalena Olesińska, Guanglu Wu, Silvia Gómez-Coca, Daniel Antón-García, Istvan Szabó, Edina Rosta, Oren A. Scherman^*

^*Corresponding author for this work

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

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Abstract

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.

Original language	English
Pages (from-to)	8806-8811
Number of pages	6
Journal	Chemical Science
Volume	10
Issue number	38
DOIs	https://doi.org/10.1039/c9sc03057c
Publication status	Published - 12 Aug 2019

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title = "Modular supramolecular dimerization of optically tunable extended aryl viologens",

abstract = "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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T1 - Modular supramolecular dimerization of optically tunable extended aryl viologens

AU - Olesińska, Magdalena

AU - Wu, Guanglu

AU - Gómez-Coca, Silvia

AU - Antón-García, Daniel

AU - Szabó, Istvan

AU - Rosta, Edina

AU - Scherman, Oren A.

PY - 2019/8/12

Y1 - 2019/8/12

N2 - 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.

AB - 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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Modular supramolecular dimerization of optically tunable extended aryl viologens

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