<b>Substituted Quinodimethans. II. Anion-radical Derivatives and Complexes of 7,7,8,8-Tetracyanoquinodimethan</b>

Melby, L. R.; Harder, Robert J.; Hertler, W. R.; Mahler, Walter; Benson, R. E.; Mochel, W. E.

doi:10.1021/ja00876a029

Cited by 1,203 publications

(484 citation statements)

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“…One detailed the charge transfer complexes formed by TCNQ, helping to launch the field of organic electronics. 38 The other described more than 20 different structures formed by the reaction of various amines with TCNQ. 39 In this study, we selected three amines: one primary (1-propylamine (PA)), one secondary (diethylamine (DEA)), and one tertiary (triethylamine (TEA)), to study dedoping effectiveness.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Quantitative Dedoping of Conductive Polymers

Jacobs¹,

Wang²,

Hafezi³

et al. 2017

Chem. Mater.

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Although doping is a cornerstone of the inorganic semiconductor industry, most devices using organic semiconductors (OSCs) make use of intrinsic (undoped) materials. Recent work on OSC doping has focused on the use of dopants to modify a material’s physical properties, such as solubility, in addition to electronic and optical properties. However, if these effects are to be exploited in device manufacturing, a method for dedoping organic semiconductors is required. Here, we outline two chemical strategies for dedoping OSC films. In the first strategy, we use an electron donor (a tertiary amine) to act as competitive donor. This process is based on a thermodynamic equilibrium between ionization of the donor and OSC and results in only partial dedoping. In the second strategy, we use an electron donor that subsequently reacts with the p-type dopant to create a nondoping product molecule. Primary and secondary amines undergo a rapid addition reaction with the dopant molecule 2,3,5,6-tetrafluoro-7,7,8,8,-tetracyanoquinodimethane (F4TCNQ), with primary amines undergoing a further reaction eliminating HCN. Under optimized conditions, films of semiconducting polymer poly(3-hexylthiophene) (P3HT) dedoped with 1-propylamine (PA) reach as-cast fluorescence intensities within 5 s of exposure to the amine, eventually reaching 140% of the as-cast values. Field-effect mobilities similarly recover after dedoping. Quantitative fluorescence recovery is possible even in highly fluorescent polymers such as PFB, which are expected to be much more sensitive to residual dopants. Interestingly, treatment of undoped films with PA also yields increased fluorescence intensity and a reduction in conductivity of at least 2 orders of magnitude. These results indicate that the process quantitatively removes not only F4TCNQ but also intrinsic p-type impurities present in as-cast films. The dedoping strategies outlined in this article are generally applicable to other p- and n-type molecular dopants in OSC films.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Quantitative Dedoping of Conductive Polymers

Jacobs¹,

Wang²,

Hafezi³

et al. 2017

Chem. Mater.

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“…The conductance is at least 50 times better than the LRS of devices with Al top electrode and hence in better accordance to results published by Melby et al on bulk Cu:TCNQ. 11 He observed semiconducting properties with low resistivity values on synthesized Cu:TCNQ bulk crystals. Samples with other bottom electrode materials display comparable characteristics.…”

mentioning

confidence: 98%

On the origin of bistable resistive switching in metal organic charge transfer complex memory cells

Kever

Böttger

Schindler

et al. 2007

Applied Physics Letters

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Electrical characteristics of Cu:tetracyanoquinodimethane (TCNQ) devices with different electrodes were studied. The comparison of impedance spectroscopic measurements on devices with Al and Pt top electrodes proved the existence of a high resistive interface layer between Cu:TCNQ and Al. An equivalent circuit was modeled and the resulting values suggest that the interface layer is composed of naturally formed aluminum oxide. Devices with deliberately formed aluminum oxide and without Cu:TCNQ were fabricated and revealed a similar behavior. The authors propose that the switching effect in Cu:TCNQ thin film devices is a Cu ion based electrochemical effect occurring in a thin aluminum oxide layer.

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“…Good acceptors such as tetracyanoethylene having a similar electron affinity to that of protonated nitrobenzene form 1 : 1 complexes with even simple aromatic π-donors such as hexamethylbenzene and these complexes have stabilities of about 30 kJ mol Ϫ1 . 39 These figures indicate that a resonance energy of 78 kJ mol Ϫ1 is reasonable for a strong double complex of DHA with protonated nitrobenzene.…”

Section: (E) Energetics Of Complex Formation Between Protonated Phno mentioning

confidence: 88%

Investigations into the mechanism of action of nitrobenzene as a mild dehydrogenating agent under acid-catalysed conditions

et al. 2003

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Protonated nitrobenzene can be used to dehydrogenate a range of hydrocarbons, which already possess at least one double bond. Kinetic and spectroscopic results, together with known electrode potentials, yield approximate limits within which protonated nitrobenzenes can be expected to effect dehydrogenation of hydroaromatic compounds. A high yielding synthesis of benzo[ j ]fluoranthene is described.

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Substituted Quinodimethans. II. Anion-radical Derivatives and Complexes of 7,7,8,8-Tetracyanoquinodimethan

Cited by 1,203 publications

References 0 publications

Quantitative Dedoping of Conductive Polymers

Quantitative Dedoping of Conductive Polymers

On the origin of bistable resistive switching in metal organic charge transfer complex memory cells

Investigations into the mechanism of action of nitrobenzene as a mild dehydrogenating agent under acid-catalysed conditions

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