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.
Highlights
Magdalena Olesinska,a Guanglu Wu,a Silvia Gomez-Coca,b Daniel Anton-Garcıa, c Istvan Szabo,b Edina Rostab and Oren A
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 pconjugated 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]
Summary
Magdalena Olesinska,a Guanglu Wu,a Silvia Gomez-Coca,b Daniel Anton-Garcıa, c Istvan Szabo,b Edina Rostab and Oren A. Edge Article cases (R 1⁄4 Me or OMe) an intense uorescence emission typical of J-aggregates (see Fig. S75†).18 A similar observation of enhanced photoluminescence for 2 : 2 complexes of CB[8] and viologen derivatives was recently described.19,20
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