Sidler, Eric and Malincik, Juraj and Prescimone, Alessandro and Mayor, Marcel. (2021) Induced axial chirality by a tight belt: naphthalene chromophores fixed in a 2,5-substituted cofacial para-phenylene-ethynylene framework. Journal of materials chemistry C, 9 (45). pp. 16199-16207.
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Abstract
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.
Faculties and Departments: | 05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor) |
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UniBasel Contributors: | Sidler, Eric and Malincik, Juraj and Prescimone, Alessandro and Mayor, Marcel |
Item Type: | Article, refereed |
Article Subtype: | Research Article |
Publisher: | Royal Society of Chemistry |
ISSN: | 2050-7526 |
e-ISSN: | 2050-7534 |
Note: | Publication type according to Uni Basel Research Database: Journal article |
Language: | English |
Identification Number: |
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edoc DOI: | |
Last Modified: | 19 Jan 2022 14:12 |
Deposited On: | 11 Dec 2021 13:20 |
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