Stacked homodimers of substituted contorted hexabenzocoronenes and their complexes with C60 fullerene
| Autor: | Ulises Rangel, Yanfei Guan, Diana Sepúlveda, Steven E. Wheeler |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
C60 fullerene
010405 organic chemistry Stereochemistry Dimer Organic Chemistry Substituent Stacking 010402 general chemistry 01 natural sciences Biochemistry Uncorrelated 0104 chemical sciences chemistry.chemical_compound Crystallography Hexabenzocoronene chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic & Biomolecular Chemistry. 15:6042-6049 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c7ob01333g |
| Popis: | Stacking interactions involving substituted contorted hexabenzocoronene (c-HBC) with C60 were studied at the B97-D3M(BJ)/TZVPP//B97-D/TZV(2d,2p) level of theory. First, we showed that substituent effects in benzeneC60 complexes are uncorrelated with those in the benzene sandwich dimer, underscoring the importance of local, direct interactions in substituent effects in stacking interactions. Second, we showed that c-HBC preferentially forms stacked homodimers over complexes with C60; however, if the bowl depth of c-HBC is increased beyond 1.25 A, the c-HBCC60 complex becomes preferred over the c-HBC homodimer. Ultimately, we showed that the perfluorination of c-HBC leads to sufficient curvature to allow the c-HBCC60 heterodimers to form preferentially over c-HBC homodimers, suggesting the possibility of the development of c-HBC derivatives that assemble into alternating stacks with C60. |
| Databáze: | OpenAIRE |
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