Evaluation of the 5-ethynyl-1,3,3-trimethyl-3H-indole ligand for molecular materials applications
David Jago
A , David C. Milan B , Alexandre N. Sobolev C , Simon J. Higgins B , Andrea Vezzoli B , Richard J. Nichols B and George A. Koutsantonis A *
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, School of Molecular Sciences, The University of Western Australia, Crawley, WA 6009, Australia.
B Department of Chemistry, University of Liverpool, Liverpool, UK.
C Centre for Microscopy, Characterisation and Analysis, The University of Western Australia, Crawley, WA 6009, Australia.
Australian Journal of Chemistry 76(4) 209-230 https://doi.org/10.1071/CH23069
Submitted: 12 April 2023 Accepted: 22 May 2023 Published: 6 July 2023
© 2023 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)
Abstract
The modification of conjugated organic compounds with organometallic moieties allows the modulation of the electronic and optoelectronic properties of such compounds and lends them to a variety of material applications. The organometallic complexes [M(Cp′)(L)n] (M = Ru or Fe; Cp′ = cyclopentadiene (Cp) or pentamethylcyclopentadiene (Cp*); (L)n = (PPh3)2 or 1,2-bi(diphenylphosphino)ethane (dppe)) and [M(L)n] (M = Ru; (L)n = (dppe)2 or (P(OEt)3)4; or M = Pt; (L)n = (PEt3)2, (PPh3)2 or tricyclohexylphosphine, (PCy3)2) modified with a 5-ethynyl-1,3,3-trimethyl-3H-indole ligand were prepared and characterised by NMR spectroscopy, IR and single-crystal X-ray diffraction. Cyclic voltammetry and IR spectroelectrochemistry of the ruthenium systems showed a single-electron oxidation localised over the M–C≡C–aryl moiety. The N-heteroatom of the indole ligand showed Lewis base properties and was able to extract a proton from a vinylidene intermediate as well as coordinate to CuI. Examples from the wire-like compounds were also studied by single-molecule break junction experiments but molecular junction formation was not observed. This is most likely attributable to the binding characteristics of the substituted terminal indole groups used here to the gold contacts.
Keywords: cyclic voltammetry, metal alkynyl, molecular materials, molecular electronics, organometallic chemistry, ruthenium, single-molecule electronics, single-molecule junction.
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