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

Sidler, Eric; Malinčík, Juraj; Prescimone, Alessandro; Mayor, Marcel 1
1 Karlsruher Institut für Technologie (KIT)

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.


Verlagsausgabe §
DOI: 10.5445/IR/1000137435
Veröffentlicht am 15.09.2021
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Nanotechnologie (INT)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2021
Sprache Englisch
Identifikator ISSN: 2050-7526, 2050-7534
KITopen-ID: 1000137435
HGF-Programm 43.32.01 (POF IV, LK 01) Molecular Materials Basis for Optics & Photonics
Erschienen in Journal of materials chemistry / C
Verlag Royal Society of Chemistry (RSC)
Band 9
Heft 45
Seiten 16199-16207
Vorab online veröffentlicht am 28.07.2021
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