Issue 45, 2021

Induced axial chirality by a tight belt: naphthalene chromophores fixed in a 2,5-substituted cofacial para-phenylene–ethynylene framework

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.

Graphical abstract: Induced axial chirality by a tight belt: naphthalene chromophores fixed in a 2,5-substituted cofacial para-phenylene–ethynylene framework

Supplementary files

Article information

Article type
Paper
Submitted
11 5 2021
Accepted
28 7 2021
First published
28 7 2021
This article is Open Access
Creative Commons BY-NC license

J. Mater. Chem. C, 2021,9, 16199-16207

Induced axial chirality by a tight belt: naphthalene chromophores fixed in a 2,5-substituted cofacial para-phenylene–ethynylene framework

E. Sidler, J. Malinčík, A. Prescimone and M. Mayor, J. Mater. Chem. C, 2021, 9, 16199 DOI: 10.1039/D1TC02180J

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