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.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
An Azobenzene-Clamped Bichromophore ; volume:4 ; number:04 ; year:2022 ; pages:153-162
Organic materials ; 4, Heft 04 (2022), 153-162

Contributor
Schmickler, Nils
Hofmeister, David A.
Bahr, Joshua
Schedlbauer, Jakob
Jester, Stefan-Sven
Lupton, John M.
Höger, Sigurd

DOI
10.1055/a-1941-7757
URN
urn:nbn:de:101:1-2022121512461234087498
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:36 AM CEST

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Associated

  • Schmickler, Nils
  • Hofmeister, David A.
  • Bahr, Joshua
  • Schedlbauer, Jakob
  • Jester, Stefan-Sven
  • Lupton, John M.
  • Höger, Sigurd

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