2009
DOI: 10.1021/ol9002459
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Simultaneous Electron Transfer from Free and Intercalated 4-Benzoylpyridinium Cations in Cucurbit[7]uril

Abstract: N-Substituted 4-benzoylpyridinium monocations form stable host-guest complexes with cucurbit[7]uril (CB[7]) in DMSO (K(eq) approximately 0.6-1.9 x 10(3) M(-1)). Observation of simultaneous reversible and quasi-reversible e-transfer processes from the free and intercalated quests, respectively, is attributed to the pre-e-transfer host-guest equilibrium. The standard rate constant for Me-BP@CB[7] (k(s) = 1.0 x 10(-4) cm.s(-1)) reflects e-transfer across 5.7 A, corresponding to the distance of the intercalated gu… Show more

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Cited by 22 publications
(22 citation statements)
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“…Both α and α′ protons are weakly shielded (Δ δ =−0.1 ppm), indicating that they are also included inside the cavity of the CB[7] macrocycle 52. Instead, the aromatic protons of the tetraphenyl moiety H‐1 and H‐2 are significantly deshielded (Δ δ =0.4 ppm) owing to their interaction with the carbonyl units around the rim of the CB[7] macrocycle; the H‐1 protons are more deshielded than the H‐2 protons due to their proximity to the rim of CB[7].…”
Section: Resultsmentioning
confidence: 99%
“…Both α and α′ protons are weakly shielded (Δ δ =−0.1 ppm), indicating that they are also included inside the cavity of the CB[7] macrocycle 52. Instead, the aromatic protons of the tetraphenyl moiety H‐1 and H‐2 are significantly deshielded (Δ δ =0.4 ppm) owing to their interaction with the carbonyl units around the rim of the CB[7] macrocycle; the H‐1 protons are more deshielded than the H‐2 protons due to their proximity to the rim of CB[7].…”
Section: Resultsmentioning
confidence: 99%
“…The two rims are formed by the glycoluril carbonyl oxygen, thereby, are negatively charged, and they develop ion‐dipole interactions with cationic guests 28, 29. Recently, taking advantage of cucurbit[7]uril's structure, various mechanically interlocked molecules including rotaxanes and poly(pseudo)rotaxanes have been synthesized by Kim,30–39 Kaifer,40–42 and others 43–56. We previously synthesized some side chain polypseudorotaxanes with viologen, and cucurbit[7]uril as a molecular bead have also been reported 52…”
Section: Introductionmentioning
confidence: 99%
“…28,29 Recently, taking advantage of cucurbit [7]uril's structure, various mechanically interlocked molecules including rotaxanes and poly(pseudo)rotaxanes have been synthesized by Kim, [30][31][32][33][34][35][36][37][38][39] Kaifer, [40][41][42] and others. [43][44][45][46][47][48][49][50][51][52][53][54][55][56] We previously synthesized some side chain polypseudorotaxanes with viologen, and cucurbit [7]uril as a molecular bead have also been reported. 52 This investigation expends our understanding about the movement on the side chains of polypseudorotaxanes.…”
mentioning
confidence: 99%
“…[21,22] CB7, in particular, has drawn much attention because of its high solubility in water. [21] CB7 has a hydrophobic internal cavity that measures 7.3 in diameter and 9.1 in height [25] and can accommodate guest substrates [21,[26][27][28] such as imidazoles, [22,29,30] stilbenes, [31][32] viologens, [32][33][34][35][36][37][38] acridiziniums, [39] pyridine/pyridiniums, [40][41] adamantanes, [28] naphthalenes, [42] and ferrocenes, [43][44] to name but a few.…”
Section: Introductionmentioning
confidence: 99%