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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 ?-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.

SUBMITTER: Olesinska M

PROVIDER: S-EPMC6849629 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Modular supramolecular dimerization of optically tunable extended aryl viologens.

Olesińska Magdalena M Wu Guanglu G Gómez-Coca Silvia S Antón-García Daniel D Szabó Istvan I Rosta Edina E Scherman Oren A OA

Chemical science 20190812 38

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 s ...[more]

PMID: 31803453

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