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DOI: 10.1055/a-1941-7757
An Azobenzene-Clamped Bichromophore
Abstract
An azo-clamped nanoscale bichromophoric cyclophane is synthesized by the intramolecular Pd(II)-catalyzed coupling of the corresponding bisacetylenic precursor. The two azo moieties in the latter can adopt cis and trans configurations. Thin-layer chromatography shows only two spots, and by scanning tunneling microscopy the trans/trans and cis/cis isomers are found. The final cyclophane does not show any switching behavior at all, but dense and wide structures are visualized after adsorption to highly oriented pyrolytic graphite. Photophysical investigations of the cyclophane show that most of the fluorescence is quenched, most likely due to the azo clamp. However, bright molecules show nearly perfect single-photon emission, meaning that efficient energy transfer between the two chromophores takes place within the molecule.
Key words
cyclophanes - azo-switches - phenylene–ethynylene–butadiynylenes - scanning tunneling microscopy - single-molecule spectroscopyPublication History
Received: 12 July 2022
Accepted after revision: 30 August 2022
Accepted Manuscript online:
12 September 2022
Article published online:
26 October 2022
© 2022. The authors. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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