ChemInform Abstract: CHEMISTRY OF QUINOMETHANS. V. REACTION OF TETRACYANOQUINODIMETHAN WITH PHENOLS

Bespalov, B. P.; Getmanova, E. V.; Титов, В. В.; Панкратов, А. А.

doi:10.1002/chin.197823153

Cited by 4 publications

(4 citation statements)

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“…Chromophore C3 was synthesized by reaction of commercially available (2-ethylanilino)-1-ethanol with 7,7,8,8-tetracyanoquinodimethane (TCNQ) in a modified two-step one-pot procedure similar to that described by Bespalov et al 27 (see Scheme 4): the initially formed addition product need not be isolated but can be converted "in-situ" into a deeply colored dye by irradiation with UV light (366 nm). The product is conveniently isolated in pure form and good yield by filtering off the precipitate and washing.…”

Section: Resultsmentioning

confidence: 99%

Reactions on Vinyl Isocyanate/Maleimide Copolymers: NLO-functionalized Polymers with High Glass Transitions for Nonlinear Optical Applications

Dörr¹,

Zentel²,

Dietrich³

et al. 1998

Macromolecules

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A new reactive copolymer system with high, but still variable glass-transition temperatures was synthesized. This was accomplished by copolymerizing various N-substituted maleimides with methylvinyl or vinyl isocyanate, so that a polymer with a 1:1 composition of the two monomers is obtained. Further functionalization is then possible with any nucleophile known from comparable low molecular weight reactions. With different substituents attached to the imide-ring, T g can be adjusted between 120 and 210 °C. Two effects of the substituent at the imide nitrogen are observed. Bulky groups reduce the mobility of the chain and lead to high T g values. A similar tendency is found for smaller, less flexible substituents. In this case, the inter- and intramolecular forces of hydrogen-bonding (urethanes) contribute to the effects for high T g's. The potential of these copolymers was highlighted here for NLO chromophores. A variety of different NLO chromophores was attached to the polymer backbone by reaction of a hydroxyalkyl-containing chromophore with the isocyanate groups, thereby forming urethane linkages between chromophore and polymer. The polymers functionalized in this way show nearly unchanged glass transition temperatures and offer thus the possibility to prepare NLO polymers with high T g values and good solubility. It is important that even base labile NLO chromophores and systems labile to radical conditions can be fixed easily. The advantage of this system is highlighted by the fixation of NLO chromophores with tricyanovinyl (C2), tricyanochinodimethane (C3) and heterocyclic acceptors (C4). With one of these systems a d 33 value of 53 pm/V could be obtained for a loading with only 12 wt % of chromophore.

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Section: Resultsmentioning

confidence: 99%

Reactions on Vinyl Isocyanate/Maleimide Copolymers: NLO-functionalized Polymers with High Glass Transitions for Nonlinear Optical Applications

Dörr¹,

Zentel²,

Dietrich³

et al. 1998

Macromolecules

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“…The coordination chemistry of TCNE and TCNQ has been much investigated,2 and their reactions with organometallic compounds include: 1) insertion into MH,3a,b MC,3c–f or MOR bonds;3g 2) [2+2], [4+2], or [3+2] additions on the ligand;4 3) α,β‐additions to an acetylide group;5 4) cycloadditions;6 and 5) insertions into an aromatic CH bond 7. Although numerous reactions of TCNE and TCNQ with organic compounds have been reported,8 only insertion reactions into a CC bond of a spiroanellated bicyclopropyl system9 or a CH bond of 4‐hydroxycoumarins,10 cyclic enol ethers,11 phenols,12 or a mesoionic thiazolium system13 have been observed.…”

Section: Methodsmentioning

confidence: 99%

Regioselective Carbon–Carbon Bond Formation Reactions between TCNE or TCNQ and a Quinonoid Ring

et al. 2006

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“…The molecules within a complex are assumed to form a sandwich with the characteristic spacing of 3.5 A [6]. The TCNQ molecule was fixed immobile with respect to the coordinate system in the X Y plane, while the NA base position varied in the plane parallel to the X Y plane.…”

Section: Calculationmentioning

confidence: 99%

Charge transfer interactions between nucleic acid bases and strong acceptors

Sheina

Radchenko

Egupov

et al. 1979

Int J of Quantum Chemistry

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The regularities of the donor-acceptor interaction of nucleic acid bases and some of their derivatives with the strong acceptor 7,7,8,8-tetracyanoquinodimethane (TCNQ) in thin amorphous films at 77 K were studied using CJV and visible spectroscopy. Purine and pyrimidine bases are shown to form charge transfer TCNQ complexes whose band energies hv,, = Zp -EA -(H* -H") are linearly dependent of the donor ionization potential I,. Calculated differences between the interaction energies of uncharged molecules and ion radicals, AE = 3.0 eV, are in good agreement with experimental variations of the complex dissociation energies in the ground and excited states, (H* -H") = 2.73 eV. Annealing of the films of complexes containing cytosine, 1-methylcytosine, uracil, and caffeine leads to ordering of their structure and the formation of ion radical salts.

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ChemInform Abstract: CHEMISTRY OF QUINOMETHANS. V. REACTION OF TETRACYANOQUINODIMETHAN WITH PHENOLS

Cited by 4 publications

References 0 publications

Reactions on Vinyl Isocyanate/Maleimide Copolymers: NLO-functionalized Polymers with High Glass Transitions for Nonlinear Optical Applications

Reactions on Vinyl Isocyanate/Maleimide Copolymers: NLO-functionalized Polymers with High Glass Transitions for Nonlinear Optical Applications

Regioselective Carbon–Carbon Bond Formation Reactions between TCNE or TCNQ and a Quinonoid Ring

Charge transfer interactions between nucleic acid bases and strong acceptors

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