Diazocine functionalized TATA Platforms

Submitting author affiliation:
Universität Kiel, Kiel, Germany

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

Published 18 Apr 2019

cc-by Logo


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

Supporting Information

Format: DOC Size: 3.3 MB   Download

How to Cite

When a peer-reviewed version of this preprint is available, 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

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.