DCNQIs—new electron acceptors for charge‐transfer complexes and highly conducting radical anion salts

Hünig, Siegfried; Erk, Peter

doi:10.1002/adma.19910030503

Cited by 121 publications

(35 citation statements)

References 80 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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confidence: 99%

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

et al. 2014

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“…100-1000 S cm À1 , at room temperature. Whereas most of the TCNQ radical salts can only be obtained in an 1:1 stoichiometry (weakly conducting), the DCNQI radical salts provide 2:1 ([DCNQI] 2 M) stoichiometry with partly filled band, a prerequisite for conductivity (3).…”

Section: Resultsmentioning

confidence: 99%

Copper Salts of Rigid N,N′-Dicyanoquinone Diimine Derivatives

Kaufman-Orenstein

Becker

Bernstein

et al. 2002

Journal of Solid State Chemistry

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“…As shown in Figure 3 (b), the monomeric compound Th 2 Bq(diHex) also received two reductions and the electrochemical reduction is reasonably accounted for by the Wurster type reductions 12 as shown in Scheme 4. P(2,6-Th 2 Bq(diHex)) received the corresponding first and second reductions with E pc of −1.14 and −1.84 V vs. Ag + /Ag, and the electrochemical reduction is accompanied by the color changes as shown in Figure 3 (a).…”

Section: Electrochemical Propertiesmentioning

confidence: 92%

Synthesis and Electrochemical Properties of New Main Chain Type Polyquinones Constituted of Thiophene-Fused Benzoquinone and Transformation of the Polymers to a Dicyanoquinonediimine Type Polymer

Shiraishi

Yamamoto

2002

Polym J

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ABSTRACT:New main chain type polyquinones, poly (3,7-dialkylbenzo[1,2-b:4,5-b ]dithiophene-4,8-dione-2,6-diyl), P(2,6-Th 2 Bq(diR)) (R = hexyl(Hex); octyl(Oct); dodecyl(Dod)), and poly(benzo[1,2-c:4,5-c ]dithiophene-4,8-dione-1,3-diyl), P(1,3-Th 2 Bq), were prepared by organometallic polycondensation. P(2,6-Th 2 Bq(diR)) was soluble in organic solvents such as chloroform and dichloromethane. P(1,3-Th 2 Bq) is soluble in CF 3 COOH, NMP, and DMI (1,3-dimethyl-2-imidazolidione). P(2,6-Th 2 Bq(diHex)) received electrochemical two step reduction with peak reduction potentials (E pc ) of −1.18 V and −1.84 V vs. Ag + /Ag, respectively. This electrochemical reduction corresponds to Wurster type reduction characteristic of quinones. P(1,3-Th 2 Bq) was also electrochemically active and its reduction took place at E pc = -1.50 V and -1.74 V vs. Ag + /Ag. The film of P(1,3-Th 2 Bq) changed its color from brown to blue (electrochromism) on the electrochemical reduction. Powder XRD patterns of P(2,6-Th 2 Bq(diR))s indicated that they assumed an ordered structure; they showed an XRD peak in a low angle region (2θ (Cu-Kα)< 7• ). The d-value of the peak increased linearly with increase in the number of the carbon of the R groups, suggesting that the d-value corresponded to a distance between the polymer main chains separated by the R groups and P(2,6-Th 2 Bq(diR)) took a stacked structure in the solid. The quinone unit of P(2,6-Th 2 Bq(diR))s was transformed to a strong electron withdrawing dicyanoquinonediimine (DC-QNI) unit by reaction with bis(trimethylsilylcarbodiimide) (TMS-N = C = N-TMS); a high degree of transformation was observed by elemental analysis. A cast film of the obtained polymer underwent the electrochemical reduction with the first E pc 1 at a very high potential of -0.56 V vs. Ag + /Ag, reflecting the high electron-withdrawing properties of the DCNQI unit. KEY WORDS π-Conjugated Polymer / Organometallic Polycondensation / Thiophene-Fused Benzoquinone / Electrochemical Response / Thiophene-Fused Dicyanoquinonediimine (DCNQI) / There has been current interest in the synthesis of novel π-conjugated polymers as interesting and useful optical and electronic materials. 1 Among the π-conjugated polymers, those constituted of redox active recurring units have attracted attention due to their interesting electrochemical behavior. Quinones are known as typical redox active compounds and a number of papers have been published about redox behaviors of quinone and its derivatives. 2 In spite of their attractive properties, examples of polymers consisting of the quinone units are still limited. 3, 4 Peover and co-workers reported the preparation of meta-bonded poly(hydroquinone) and its electrochemical responses. 3a Arai and co-workers reported electrochemical synthesis of poly(mercapto-p-benzoquinone) and poly(mercapto-p-hydroquinone). 3b However, in these cases, the bonding modes of the monomeric units in the polymer chains are not controlled and their chemical properties have not been revealed well.Previously, we rep...

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DCNQIs—new electron acceptors for charge‐transfer complexes and highly conducting radical anion salts

Cited by 121 publications

References 80 publications

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

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

Copper Salts of Rigid N,N′-Dicyanoquinone Diimine Derivatives

Synthesis and Electrochemical Properties of New Main Chain Type Polyquinones Constituted of Thiophene-Fused Benzoquinone and Transformation of the Polymers to a Dicyanoquinonediimine Type Polymer

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