Dimeric capsules with a nanoscale cavity for fullerene encapsulation
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- Dimeric capsules with a nanoscale cavity for fullerene encapsulation
- Park, Seong Jin; Kwon, Oh Hoon; Lee, Kyung-Sik; Yamaguchi, Kentaro; Jang, Du-Jeon; Hong, Jong-In
- Issue Date
- WILEY-V C H VERLAG GMBH
- CHEMISTRY-A EUROPEAN JOURNAL, v.14, no.17, pp.5353 - 5359
- The acid-assisted and guest-induced formation of superstructures was achieved by the addition of haloacetic acids to a toluene solution of the resorcinarene derivatives 1 and fullerenes. The formation of dimeric superstructures that encapsulated a nanosized guest molecule was observed when appropriate acids, such as haloacetic acids, and suitable guest molecules, such as fullerenes, were coadded to a toluene solution of cavitand 1 that has four pyridine units, whereas a complicated equilibrium between several species was detected without fullerenes, and the formation of discrete superstructures was not monitored in the absence of haloacetic acids. The spectroscopic data indicate that the formed fullerene-encapsulated complexes have the structure of 2. These complexes are self-assembled through pyridinium-anion-pyridinium interactions and by π-π and van der Waals interactions. The rate of decomplexation of 2 is estimated to be 3.1 s -1 from a 2D exchange NMR spectrum. The fullerene encapsulation process can be controlled by modifying the amounts of acids used, changing the temperature of the system, altering the ratio of acid/base, and even through varying the solvent polarity. Moreover, the fluorescence spectra show bandnarrowing spectral changes and a retardation of the relaxation characteristics of isolated and isotropic fullerenes, which indicates that the environmental change around fullerene is induced upon its encapsulation.
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