Induced axial chirality by a tight belt: naphthalene chromophores fixed in a 2,5-substituted cofacial para-phenylene-ethynylene framework
| Autor: | Eric Sidler, Juraj Malinčík, Marcel Mayor, Alessandro Prescimone |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Journal of materials chemistry / C, 9 (45), 16199-16207 Journal of Materials Chemistry. C |
| ISSN: | 2050-7526 2050-7534 |
| Popis: | We report the design of a synthetically easy accessible axial chirality-inducing framework for a chromophore of choice. The scaffold consists of two basic para-phenylene-ethynylene backbones separated by laterally placed corner units. Substitution with an inherently achiral chromophore at the 2 and 5 positions of the central phenylene excitonically couples the chromophore associated transition and thereby results in chiroptical properties. Using 6-methoxynaphthalene as a model chromophore, we present the synthesis, structural analysis and spectroscopic investigation of the framework. The chiral framework was synthesized in three straightforward synthetic steps and fully characterized. The obtained racemic compounds were resolved using HPLC and assignment of the absolute configuration was performed using the exciton chirality method, crystallography and DFT calculations. This simple yet potent framework might prove useful to enrich the structural diversity of chiral materials. We report the design of a synthetically easy accessible axial chirality-inducing framework for an achiral chromophore of choice. The spatial arrangement excitonically couples the chromophores and thus results in intense molar dichroism. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|