Enantiopure Synthesis of [5]Helicene Based Molecular Lemniscates and their use in Chiroptical Materials
DOI: 10.14469/hpc/3901 Metadata
Created: 2018-03-13 17:57
Last modified: 2024-02-11 15:38
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: ANDREA TADDEUCCI Co-author: Christian Johannessen Co-author: Dan Pantoș Co-author: David Carbery Co-author: Fabienne Pradaux-Caggiano Co-author: Giuliano Siligardi Co-author: Lauren Hatcher Co-author: Leah White Co-author: Thierry Verbiest Co-author: Tiberiu-Marius Gianga
Description
The ability to synthesise lemniscular molecules to allow for the study and application of their chiroptical properties is a notable technical challenge. Herein, we report the design and synthesis of enantiomers of a [5]helicenoid derived molecular lemniscate, in which two homochiral helicenes are linked via the formation of two azine motifs. To the best of our knowledge, this represents the first enantiopure route to helicene-derived molecular lemniscates. We demonstrate that these molecules, and their helicenoid constituents, are also excellent chiral dopants that induce dissymmetry in the ground and excited states of the achiral emissive polymer F8BT, leading to high CPL activity. The ability to control the handedness of the helicenoid dopants via enantiopure synthesis affords control of the sign of CP emission. This manipulation of circularly polarised light is of great interest for next-generation optoelectronic technologies.
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/4937 | FAIR Data table. VCD spectra and geometries calculated for a Single Enantiomer Lemniscular (Figure-of-Eight) Bisazine |
| 10.14469/hpc/4934 | ECD. Synthesis and Study of a Single Enantiomer Lemniscular (Figure-of-Eight) Bisazine |
| 10.14469/hpc/4935 | ORD. Synthesis and Study of a Single Enantiomer Lemniscular (Figure-of-Eight) Bisazine |
| 10.14469/hpc/4936 | VCD. Synthesis and Study of a Single Enantiomer Lemniscular (Figure-of-Eight) Bisazine |
| 10.14469/hpc/4938 | Link Analysis. Synthesis and Study of a Single Enantiomer Lemniscular (Figure-of-Eight) Bisazine |
| 10.14469/hpc/13570 | Enantiopure Synthesis of [5]Helicene Based Molecular Lemniscates and their use in Chiroptical Materials: ORCA Calculations |
| 10.14469/hpc/13743 | NMR Data for Enantiopure Synthesis of [5]Helicene Based Molecular Lemniscates and their use in Chiroptical Materials |
Associated DOIs
| Current dataset ... | DOI | Description |
|---|---|---|
| References | 10.1021/ja710438j | Intrinsically Chiral Aromaticity. Rules Incorporating Linking Number, Twist, and Writhe for Higher-Twist Möbius Annulenes |
| References | 10.1021/ol901172g | The Chiro-optical properties of a Lemniscular Octaphyrin |
| References | 10.25504/FAIRsharing.LEtKjT | Imperial College Research Data Repository; Imperial College Research Data Repository |