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Updated: Jan 20, 2026

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Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms.

Roland Löw1, Talina Rusch2, Tobias Moje1

  • 1Otto Diels Institute for Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, 24118 Kiel, Germany.

Beilstein Journal of Organic Chemistry
|August 31, 2019
PubMed
Summary
This summary is machine-generated.

Triazatriangulenium (TATA) and trioxatriangulenium (TOTA) ions enable ordered surface monolayers for functional molecules. Researchers are investigating if accelerated isomerization and spin-change mechanisms apply to [2+2] cycloreversions of norbornadienes and quadricyclanes on these platforms.

Keywords:
TATA platformTOTA platform[2 + 2] cycloaddition[2 + 2] cycloreversionnorbornadienephotochemical isomerizationquadricyclaneself-assembled monolayersthermal isomerization

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Area of Science:

  • Surface Chemistry and Nanotechnology
  • Photochemistry and Molecular Switches

Background:

  • Triazatriangulenium (TATA) and trioxatriangulenium (TOTA) ions form ordered monolayers on surfaces like Au(111).
  • Functional groups attached to TATA/TOTA platforms protrude upright, enabling surface-initiated reactions.
  • Azobenzene-TATA systems show rapid cis→trans isomerization via a singlet→triplet→singlet mechanism on metal surfaces.

Purpose of the Study:

  • To investigate the applicability of accelerated rates and spin-change mechanisms to [2+2] cycloreversions.
  • To explore norbornadiene (NBD) and quadricyclane (QC) derivatives on TATA and TOTA platforms for surface-based photochemical studies.

Main Methods:

  • Synthesis of TATA and TOTA platforms functionalized with norbornadiene (NBD) and quadricyclane (QC) moieties.
  • Adsorption of these functionalized platforms onto atomically flat surfaces, such as Au(111), to form ordered monolayers.
  • Spectroscopic and surface science techniques to monitor and analyze photochemical transformations, specifically [2+2] cycloreversions (QC→NBD).

Main Results:

  • Successful preparation of NBD and QC attached to TATA and TOTA platforms.
  • Demonstration of these molecules' ability to form ordered monolayers on metal surfaces.
  • Establishment of a system to test accelerated photochemical reactions and spin-change mechanisms in [2+2] cycloreversions.

Conclusions:

  • TATA and TOTA platforms are versatile for immobilizing functional molecules on surfaces.
  • The study provides a novel system to investigate the dynamics of [2+2] cycloreversions on surfaces.
  • Potential for accelerated photochemical reactions and spin-change mechanisms in QC→NBD transformations is under examination.