| Autor: |
Lehnherr, Dan, Chen, Chen, Pedramrazi, Zahra, DeBlase, Catherine R, Alzola, Joaquin M, Keresztes, Ivan, Lobkovsky, Emil B, Crommie, Michael F, Dichtel, William R |
| Rok vydání: |
2016 |
| Předmět: |
|
| Zdroj: |
Chemical science, vol 7, iss 10 |
| Popis: |
A Cu-catalyzed benzannulation reaction transforms ortho(arylene ethynylene) oligomers into ortho-arylenes. This approach circumvents iterative Suzuki cross-coupling reactions previously used to assemble hindered ortho-arylene backbones. These derivatives form helical folded structures in the solid-state and in solution, as demonstrated by X-ray crystallography and solution-state NMR analysis. DFT calculations of misfolded conformations are correlated with variable-temperature 1H and EXSY NMR to reveal that folding is cooperative and more favorable in halide-substituted naphthalenes. Helical ortho-arylene foldamers with specific aromatic sequences organize functional π-electron systems into arrangements ideal for ambipolar charge transport and show preliminary promise for the surface-mediated synthesis of structurally defined graphene nanoribbons. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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