Diazocine functionalized TATA Platforms

  1. Roland LöwORCID Logo,
  2. Talina Rusch,
  3. Fynn Röhricht,
  4. Olaf M. Magnussen and
  5. Rainer Herges ORCID Logo

Submitting author affiliation: Universität Kiel, Kiel, Germany

Beilstein Arch. 2019, 201911. doi:10.3762/bxiv.2019.11.v1

Published 18 Apr 2019

  • Preprint

Abstract

Recently, it has been shown that the thermochemical cistrans isomerization of azobenzenes is accelerated by a factor of more than 1000 by electronic coupling to a gold surface via a conjugated system with 11 bonds and a distance of 14 Å. The corresponding molecular architecture consists of a platform (triazatriangulenium (TATA)) which adsorbs on the gold surface, with an acetylene spacer standing upright, like a post in the middle of the platform and the azobenzene unit mounted on top. The rate acceleration is due to a very peculiar thermal singlet-triplet-singlet mechanism mediated by bulk gold. To investigate this mechanism further and to examine scope and limitation of the “spin-switch catalysis” we now prepared analogous diazocine systems. Diazocines, in contrast to azobenzenes, are stable in the cis configuration. Upon irradiation with light of 405 nm the cis configuration isomerizes to the trans form, which slowly returns back to the stable cis isomer. To investigate the thermal transcis isomerization as a function of the conjugation to the metal surface, we connected the acetylene spacer in meta (weak conjugation) and in para (strong conjugation) position. Both isomers form ordered monolayers on Au(111) surfaces.

Keywords: diazocine, TATA platform, self-assembled monolayers, cis-trans isomerization, photochrome

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When a peer-reviewed version of this preprint is available in the Beilstein Journals, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Löw, R.; Rusch, T.; Röhricht, F.; Magnussen, O. M.; Herges, R. Beilstein Arch. 2019, 201911. doi:10.3762/bxiv.2019.11.v1

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