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CC BY-NC-ND 4.0 · Organic Materials 2022; 4(03): 102-126
DOI: 10.1055/a-1926-6340
Supramolecular Chemistry
Original Article

2,5-Diaryl 6-hydroxyphenalenones for Single-Molecule Junctions

David Vogel 
a   Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland
,
Luca Ornago 
b   Kavli Institute of Nanoscience, Delft University of Technology, Lorentzweg 1, 2628 CJ Delft, The Netherlands
,
Christina Wegeberg 
a   Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland
,
Alessandro Prescimone 
a   Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland
,
Herreder Zant van 
b   Kavli Institute of Nanoscience, Delft University of Technology, Lorentzweg 1, 2628 CJ Delft, The Netherlands
,
Marcel Mayor 
a   Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland
c   Institute for Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), P. O. Box 3640, 76021 Karlsruhe, Germany
d   Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-Sen University, Guangzhou 510274, P. R. of China
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Abstract

A modular access to 2,5-diaryl 6-hydroxyphenalenone derivatives is developed and demonstrated by a small series of 5 molecules. Within this series, the structures 1 and 2 expose terminal methylsulfanyl anchor groups, enabling their integration in a single-molecule junction. The modular synthesis is based on Suzuki cross-coupling of the aryl substituents as boronic acid precursors with 5,8-dibromo-2-(tert-butyl)-4,9-dimethoxy-2,3-dihydro-1H-phenalen-1-one, and the subsequent transformation of the product to the desired 2,5-diaryl 6-hydroxyphenalenone in a reduction/deprotection sequence. The new structures are fully characterized and their optical and electrochemical properties are analysed. For the derivatives 1 and 2 suitable for single-molecule junctions, the corresponding oxophenalenoxyl radicals 1R and 2R were obtained by oxidation and analysed by electron paramagnetic resonance spectroscopy. Preliminary mechanical break junction experiments with 1 display the structureʼs ability to form transient single-molecule junctions. The intention behind the molecular design is to profit from the various redox states of the structure (including the neutral radical) as a molecular switch in an electrochemically triggered single-molecule transport experiment.

Key words

oxophenalenoxyl radicals - 6-hydroxyphenalenone - molecular switches - voltammetry - organic chemistry - molecular break junctions

Supporting Information



Publication History

Received: 30 June 2022

Accepted after revision: 12 August 2022

Accepted Manuscript online:
17 August 2022

Article published online:
20 September 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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