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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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-10, Vol.1 (38), p.886-8811
Main Authors: Olesi ska, Magdalena, Wu, Guanglu, Gómez-Coca, Silvia, Antón-García, Daniel, Szabó, Istvan, Rosta, Edina, Scherman, Oren A
Format: Article
Language:English
Subjects:
Aqueous solutions
Aromatic compounds
Dimerization
Dimers
Excimers
Modular design
NMR
Nuclear magnetic resonance
Self-assembly
Titration calorimetry
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Summary: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. Cucurbit[8]uril (CB[8]) mediated assembly of extended aryl viologens (EVs) into optically tunable dimers is reported for the first time.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc03057c