7,7,8,8-Tetracyanoquinodimethane in Addition, Substitution, and Complex Formation Reactions

Bespalov, B. P.; Титов, В. В.

doi:10.1070/rc1975v044n12abeh002559

Cited by 50 publications

(13 citation statements)

References 23 publications

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“…Stable strong electron acceptors, such as tetracyanoethene (TCNE) 1 and 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2 are in high demand. 3,4 Strong acceptors are of interest as dopants in the fabrication of optical light-emitting diodes (OLEDs) and solar cells.…”

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confidence: 99%

New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

et al. 2007

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Donor-substituted 1,1,2,4,4-pentacyanobuta-1,3-dienes and a cyclohexa-2,5-diene-1,4-diylidene-expanded derivative were prepared by a [2 + 2] cycloaddition of tetracyanoethene (TCNE) or 7,7,8,8-tetracyanoquinodimethane (TCNQ) to anilino-substituted cyanoalkynes, followed by retro-electrocyclisation; they feature intense bathochromically-shifted intramolecular charge-transfer bands and undergo their first one-electron reductions at potentials similar to those reported for TCNE and TCNQ.

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confidence: 99%

New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

et al. 2007

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“…3,4,5 Recently this class of compounds has attracted interest because of their non-linear optical properties. While much of this work has focussed on single crystals and the large molecular hyperpolarisibity (β) of these compounds 6,7,8,9 they have also been shown, both experimentally and theoretically, to possess large ground state dipole moments (µ).…”

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et al. 2001

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Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. These included alcohol solutions and crystals at room temperature and glass forming solvents and polymer films as a function of temperature. The fluorescence quantum yields and Stokes' shifts were found to be very sensitive to the matrix. Crystal structure data shows that the molecules are non-planar in the ground state. The matrix effect is discussed in terms of the conformational change during photo-excitation and the constraint imposed on this by the matrix.

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“…This experimental finding indicates an existence of some kind of complex between 8CB (or 6CB) and TCNQ molecules. The ability of TCNQ, a strong n-electron compound, to form different types of complexes (also with aromatic amines) has been known for a long time (for review see Bespalov and Titov, 1975). The electronic absorption spectra of such TCNQ molecular complexes also contain, apart from the absorption bands of the donor and acceptor, a charge transfer band (CT).…”

Section: Discussionmentioning

confidence: 99%

“…The electronic absorption spectra of such TCNQ molecular complexes also contain, apart from the absorption bands of the donor and acceptor, a charge transfer band (CT). The appearance of the latter is a characteristic feature of the formation of complexes with TCNQ and is frequently used (Bespalov and Titov, 1975). The position of this band can vary within very wide limits (from 480 to 1285 nm).…”

Section: Discussionmentioning

confidence: 99%

Light‐induced Electrical Effects in a Liquid Crystal BLM Containing TCNQ

Salamon

Tien

1988

Photochem & Photobiology

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Abstract— The light‐induced capacitance changes and also both photovoltage and photocurrent under continuous illumination have been investigated in pigmented liquid crystal bilayer membranes (PBLM)‡ containing TCNQ as photosensitizer with Na2SO3 electron donor on one side and methylene blue electron acceptor on the other side. The results have shown that TCNQ in cyanobiphenyl membrane produces a unique photoactive BLM system in which all three main parameters (conductivity, capacity and voltage across the membrane) are in a wide range altered by the light. It is shown that a TCNQ‐cyanobiphenyl charge transfer complex is responsible for the observed photochanges. The possible mechanism of photoinduced electrical effects in this type of PBLM is discussed.

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7,7,8,8-Tetracyanoquinodimethane in Addition, Substitution, and Complex Formation Reactions

Cited by 50 publications

References 23 publications

New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

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Light‐induced Electrical Effects in a Liquid Crystal BLM Containing TCNQ

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