Design and synthesis of TCNQ and DCNQI type electron acceptor molecules as precursors for ‘organic metals’

Martı́n, Nazario; Segura, José L.; Seoane, Carlos

doi:10.1039/a702314f

Cited by 138 publications

(90 citation statements)

References 96 publications

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“…DCNQI is an electron acceptor molecule, nearly as strong as 7,7,8,8-tetracyanoquinodimethane (TCNQ), [17][18] and it belongs to a family of molecules which form a large number of charge transfer and coordination compounds exhibiting metallic conductivity. 19 The stereochemistry of DNCQI and its derivatives has been thoroughly investigated.…”

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confidence: 99%

Charge-Transfer-Induced Isomerization of DCNQI on Cu(100)

et al. 2014

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This article reports on the temperature-controlled irreversible transition between the two isomeric forms of the strong electron acceptor dicyano-p-quinonediimine (DCNQI) on the Cu(100) surface. A combination of experiment (time-resolved, variable-temperature scanning tunneling microscopy, STM) and theory (density functional theory, DFT) shows that the isomerization barrier is lower than in the gas phase or solution due to the fact that charge transfer from the substrate modifies the bond configuration of the molecule, aromatizing the quinoid ring of DCNQI and enabling a more free rotation of the cyano groups with respect to the molecular axis.

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Charge-Transfer-Induced Isomerization of DCNQI on Cu(100)

et al. 2014

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“…Ar epresentative quinoidalc ompound is 7,7,8,8-tetracyano-1,4-quinodimethane (TCNQ,F igure 1a)a nd its derivatives, [1] whichc an function as strong electron acceptors in conducting charge-transfer (CT) salts, [2] efficient p-dopants in organic electronics, [3] and components of organicm agnets. Ar epresentative quinoidalc ompound is 7,7,8,8-tetracyano-1,4-quinodimethane (TCNQ,F igure 1a)a nd its derivatives, [1] whichc an function as strong electron acceptors in conducting charge-transfer (CT) salts, [2] efficient p-dopants in organic electronics, [3] and components of organicm agnets.…”

Section: Introductionmentioning

confidence: 99%

“…[17] In this work, we have designed as eries of triads consisting of the largely p-extended acenedithiophenediones and two flankingt hiophenes, or dithienyl acenedithiophenediones, that is, 3,7-bis [5-(triisopropylsilyl) dithiophene-2,7-dione (4;F igure 2). [18] In fact, the flanking thiophenesc an function ash andles for furtherc hemical modifications at the reactive a-positions, which are here protected by triisopropylsilyl (TIPS) groups (1)(2)(3)(4). [18] In fact, the flanking thiophenesc an function ash andles for furtherc hemical modifications at the reactive a-positions, which are here protected by triisopropylsilyl (TIPS) groups (1)(2)(3)(4).…”

Section: Introductionmentioning

confidence: 99%

Dithienyl Acenedithiophenediones as New π‐Extended Quinoidal Cores: Synthesis and Properties

Kawabata

Osaka

Sawamoto

et al. 2017

Chemistry A European J

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We have synthesized two isomeric pairs of benzo- and naphthodithiophenediones with two flanking thiophenes and characterized them by single-crystal X-ray analysis, cyclic voltammetry, steady-state optical electronic absorption and emission spectroscopies, transient absorption spectroscopy, and vibrational spectroscopies with in situ spectroelectrochemistry techniques, and then compared them with the thieno[3,2-b]thiophene-2,5-dione counterpart that we previously reported. The results show that the central acenedithiophenedione cores have quinoidal conjugation with closed-shell character. The π-extension of the quinoidal core raises (lowers) the HOMO (LUMO) energy levels of the triads, resulting in the drastic reduction of their energy gaps from approximately 2.0 eV to 1.1 eV. Owing to the electron-withdrawing nature of the carbonyl terminal group at the quinoidal core, the triads have low-lying LUMO energy levels ranging from -3.9 eV to -4.3 eV, and can be regarded as strong electron-acceptor building units. Interestingly, the pairs of structural isomers have similar electronic structures in both the neutral and charged states despite the different shapes (linear and angular) and/or symmetry (C and C ) of the acenedithiophenedione cores.

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“…1 In an effort to make organic polymer acceptors, there have been a few, partially successful, efforts to functionalize TCNQ into polymer backbone. 2 These polymer acceptors have the potential to be used as the complementary reducible parts of oxidizable polymeric materials in applications such as polymer batteries and electrochemical capacitors. 3 Whereas many oxidized polymers have been developed and studied since the early 1980s, 4 less effort has gone into preparing polymeric electron accepting materials.…”

Section: Introductionmentioning

confidence: 99%

Pendent polymers of 1-methyl-2-oxo-4,5-dicyanoimidazole and their electrochemical properties

Jang

Rasmussen

2000

J. Polym. Sci. A Polym. Chem.

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The electron accepting 1-methyl-4,5-dicyanoimidazole group was attached to vinyl polymers, via an alkoxy link, by nucleophilic aromatic substitution (NAS) of 1-methyl-2-fluoro-4,5-dicyanoimidazole (1) with poly(vinyl alcohol), or conventional polymerizations of vinyl monomers containing 1-methyl-2-oxo-4,5-dicyanoimidazole. The cyclic voltammetry (CV) studies show that monomeric and oligomeric model compounds are electrochemically quasi-reversible and the degree of reversibility decreases as dicyanoimidazoles become more proximate within a molecule. On the other hand, the polymers show much less reversible reduction waves at Ϫ2.6ϳϪ2.7 V vs Ag/Ag ϩ , suggesting that there are chemical reactions among the pendent groups reduced at relatively high potential.

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Design and synthesis of TCNQ and DCNQI type electron acceptor molecules as precursors for ‘organic metals’

Cited by 138 publications

References 96 publications

Charge-Transfer-Induced Isomerization of DCNQI on Cu(100)

Charge-Transfer-Induced Isomerization of DCNQI on Cu(100)

Dithienyl Acenedithiophenediones as New π‐Extended Quinoidal Cores: Synthesis and Properties

Pendent polymers of 1-methyl-2-oxo-4,5-dicyanoimidazole and their electrochemical properties

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