A combinatorial approach to to improving the performance of azoarene photoswitches
DOI: 10.14469/hpc/6203 Metadata
Created: 2019-10-07 12:01
Last modified: 2019-11-10 15:34
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: Aditya Thawani
Description
Azoarenes remain privileged photoswitches – molecules that can be interconverted between two states using light – enabling a huge range of light addressable multi-functional systems and materials. Two key innovations to improve the addressability and Z-isomer stability of the azoarenes has been ortho-substitution of the benzene ring(s) or replacement of one of the benzenes for a pyrazole (to give arylazopyrazole switches). Here we study the combination of such high-performance features within a single switch architecture. Through computational analysis and experimental measurements of representative examples, we demonstrate that ortho-benzene substitution of the arylazopyrazoles drastically increases the Z-isomer stability and allows further tuning of their addressability. This includes the discovery of new azopyrazoles with a Z-isomer thermal half-life of ~46 years. Such results therefore define improved designs for high performance azo switches, which will allow for high precision optically-addressable applications using such components.
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/6208 | 4pzH F2 |
| 10.14469/hpc/6212 | 3-(2-(2,6-difluorophenyl)hydrazineylidene)pentane-2,4-dione |
| 10.14469/hpc/6206 | 4pzMe OMe2 |
| 10.14469/hpc/6209 | 4pzMe Cl2 |
| 10.14469/hpc/6210 | 3-(2-(2,6-dichlorophenyl)hydrazineylidene)pentane-2,4-dione |
| 10.14469/hpc/6204 | 3-(2-(2,6-dimethoxyphenyl)hydrazineylidene)pentane-2,4-dione |
| 10.14469/hpc/6211 | 4pzMe F2 |