Gold Complexes with Dithiothiophene Ligands: A Metal Based on a Neutral Molecule

Belo, Dulce; Alves, Helena; Lopes, Elsa B.; Duarte, M. Teresa; Gama, V.; Henriques, R.T.; Almeida, Manuel; Pérez‐Benítez, Aarón; Rovira, Concepció; Veciana, Jaume

doi:10.1002/1521-3765(20010119)7:2<511::aid-chem511>3.0.co;2-5

Cited by 114 publications

(38 citation statements)

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“…Films conductive performance was highly dependent on the solvent, even if these presented similar solubility compatibility, which affected mostly the film morphology. The chosen materials were [Ni(dtdt) 2 ](dtdt = dihydrothiophenetetrathiafulvalenedithiolen e) 10 and [Au(α-tpdt) 2 ] (α-tpdt = 2,3-thiophenedithiolene) 13 ( Fig. 1a).…”

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Conducting films based on single-component molecular metals

et al. 2015

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We demonstrate that single component molecular metals can be used as conductive inks for printed electronics. The resistance is 0.3 kΩ/sq, in a Ni complex, one order of magnitude better than commercial carbon based conductive inks.Conductive inks are particularly attractive for electronic devices using printing or other solution processing technology such as flexible displays, photovoltaics or sensors integrated in textiles or paper . Moreover, functionalisation of these materials is difficult, hindering a more selective interface 4 . Even in conducting polymers, the best strategy to modify their properties is mixing compounds, making it difficult to control the reproduci bility and anticipate the final effect 5 . Small organic molecules have proven to be easier to control by strategic chemical modification, both the electronic properties and chemical sensitivity 6 . That is the case, for instance, of the perylenediimides, used as organic semiconductor in field-effect transistors. The introduction of electronegative groups, such as halogens, on bay positions of the core aromatic scaffold can modify the energy levels with direct consequences on the transport and electrochemical properties, whereas additional side groups in the imide positions lead to changes in solubility and fluorescence 7 . To reach metallic conduction, an appropriate combination of molecular order and chemical interactions are necessary for producing charge carriers drift with minimal scattering. Defects and steric constrains, seriously affect the transport mechanism and, as a result, only a few materials have been developed 8 .Single component molecular metals (SCMM) are a recent class of molecular conductors composed of a single neutral molecule, with a transition metal bisdithiolene core, offering the simplicity of only one molecule to be engineered and processed. Conductivity as high as 400 S/cm and even superconductivity has been reported, both measured in singlecrystal 9 . In compressed polycrystalline powder samples values decrease substantially due to grain-boundary effect, yet, some tetrathiafulvalenedithiolate compounds were able to achieve 200 S/cm 10 . Even if these materials present low solubility, a trimethylenetetrathiafulvalenedithiolate derivative was successfully used as a conductive film 11 , whereas a thiophenedithiolene derivative was used as flexible metallic films for piezo-resistive sensors. However, these were achieved either as a highly viscose mixture that becomes rapidly rigid, or as a bilayer composite film prepared in situ by a modified reticulated doping technique 12 , which are incompatible with printing process. Moreover, similar approaches for compounds with more extended chemical structure and higher conductivity were restricted by their lower solubility.In this communication, we report the fabrication of a highly conductive and durable SCMM films using a solution process method compatible with printing technology. To the best of our knowledge, this is the first evidence of using a single component m...

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“…1a). The two compounds were readily synthesised using procedures already developed in our previous work and available in literature 10,13 . A 2 wt% solution was prepared in different high purity solvents.…”

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Conducting films based on single-component molecular metals

et al. 2015

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“…The distance of the close contacts is comparable to that observed for a black-colored spin-carrying benzoquinone (2.796 Å), in which a distinct CT band is observed in the diffuse reflectance UV-VIS spectrum in the solid state [5]. Thus, the formation of a single-component CT crystal is apparent for 3a to reflect the black color of the crystal.…”

Section: Crystal Structures and Magnetic Properties Of Tcnq Derivativmentioning

confidence: 99%

“…On the other hand, several single-component molecular conductors [4][5][6][7]. In turn, we found recently that some benzoquinone derivatives carrying TEMPO radical (e.g., 1a, 1b in Scheme 1) form single component CT complexes by assembling themselves, where benzoquinone works as an acceptor and the TEMPO group as a donor [8].…”

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Single-Component Charge-Transfer Crystals Based on Spin-Carrying TCNQ (7,7,8,8-Tetracyanoquinodimethane) Derivatives

et al. 2012

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Three TCNQ derivatives carrying nitroxide radicals (3a-3c) were prepared and were found to form single-component charge-transfer (CT) complexes by self-assembly, in which outer nitroxide groups of a couple of different molecules work as donors and the inner TCNQ unit of another molecule as an acceptor. While the CT interactions found for the TEMPO (2,2,6,6-tetramethylpiperidin-1-oxy) derivative 3a and the PROXYL (2,2,5,5-tetramethylpirrolidin-1-oxy) derivative 3b are point-to-face fashion between the oxygen atom of each nitroxide group and the six-membered ring of inner TCNQ unit, the CT interactions found for the PO (2,2,5,5-tetramethyl-3-pyrrolin-1-oxy) derivative 3c are point-to-point contacts between the oxygen atoms of outer nitroxide groups and the carbon atoms of a couple of cyano groups.

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“…The formation of chains and of an unusual network of rectangular rings will be shown and described. [ (a-tpdt=2,3-thiophenedithiolate, dtpdt=4,5-dihidro-2,3-thiophenedithiolate, and tpdt=3,4-thiophenedithio late with M=Au, Ni, Co, Cu and Pt) [1,2] and evaluate their potential as building blocks for the preparation of new electric or magnetic materials. The crystal structure of these complexes, obtained by single crystal x-ray diffraction show in general a square planar coordination geometry (y=2) except for Cu which presents the less common geometry based Cu 4 S 6 clusters with y=3 as for Cu 4 (tpdt) 3 .…”

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