Selective supramolecular porphyrin/fullerene interactions
| Autor: | Boyd, PDW, Hodgson, MC, Rickard, CEF, Oliver, AG, Chaker, L, Brothers, PJ, Bolskar, RD, Tham, FS, Reed, CA |
|---|---|
| Rok vydání: | 1999 |
| Předmět: | |
| Zdroj: | Journal of the American Chemical Society, vol 121, iss 45 Boyd, PDW; Hodgson, MC; Rickard, CEF; Oliver, AG; Chaker, L; Brothers, PJ; et al.(1999). Selective supramolecular porphyrin/fullerene interactions. Journal of the American Chemical Society, 121(45), 10487-10495. doi: 10.1021/ja992165h. UC Riverside: Retrieved from: http://www.escholarship.org/uc/item/5tp8m4fx |
| Popis: | Naturally assembling cocrystallates of C60 and C70 fullerenes with tetraphenylporphyrins (H2TPP · C60 · 3 toluene, 1; H2T(3,5-dibutyl)PP · C60, 2; H2T(3,5-dimethyl)PP · 1.5C60 · 2 toluene, 3; H2T(piv)PP · C60, 4; H2T(3,5-dimethyl)PP · C70 · 4 toluene, 5; ZnTPP · C70, 6; NiT(4-methyl)PP · 2C70 · 2 toluene, 7) show unusually short porphyrin/fullerene contacts (2.7-3.0 Å) compared with typical π-π interactions (3.0-3.5 Å). In the C60 structures, an electron-rich, 6:6 ring juncture, C-C bond lies over the center of the porphyrin ring. In the C70 structures, the ellipsoidal fullerene makes porphyrin contact at its equator rather than its poles; a carbon atom from three fused six-membered rings lies closest to the center of the porphyrin. These structures provide an explanation for the manner in which tetraphenylporphyrin-appended silica stationary phases effect the chromatographic separation of fullerenes. The interaction of the curved π surface of a fullerene with the planar π surface of a porphyrin, without the need for matching convex with concave surfaces, represents a new recognition element in supramolecular chemistry. NMR measurements show that this interaction persists in toluene solution, suggesting a simple way to assemble van der Waals complexes of donor-acceptor chromophores. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|