Isolation of p-tricyanovinylphenyldicyanomethide ion via a [2+2] cycloaddition of 7,7,8,8-tetracyanoquinodimethane (TCNQ) molecules

Lv, Qiying; Tang, Shidi; Tan, Xing-Wu; Lei, Wen-Jun; Wang, Ye; Lin, Houkeng; Wu, Ze-Quan; Zhan, Shu‐Zhong

doi:10.1016/j.jorganchem.2009.06.016

Cited by 7 publications

(2 citation statements)

References 34 publications

(31 reference statements)

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“…62 Since this initial report, several other examples of TCNQ-derived expanded TCBDs have been reported. [63][64][65][66][67][68] Importantly, the reaction is completely regioselective with respect to TCNQ, occurring exclusively at one exocyclic CQC double bond adjacent to the DCV moiety and not at the endocyclic double bonds. A similar regioselectivity was previously observed in the Diels-Alder reaction of TCNQ with in situ generated ortho-quinodimethane, reported by Martı´n and Hanack.…”

Section: Donor-substituted Expanded 7788-tetracyanoquinodimethanesmentioning

confidence: 99%

Non-planar push–pull chromophores

2010

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The development of a unique class of non-planar push-pull chromophores by means of [2 + 2] cycloaddition, followed by cycloreversion, of electron-deficient olefins, such as tetracyanoethene (TCNE), 7,7,8,8-tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F(4)-TCNQ), as well as dicyanovinyl (DCV) and tricyanovinyl (TCV) derivatives, to donor-substituted alkynes is explored in this feature article. This high-yielding, "click-chemistry"-type transformation with acetylenic dendrimers affords dendritic electron sinks capable of multiple electron uptake within a narrow potential range. An [AB]-type oligomer with a dendralene backbone was synthesised by a one-pot, multi-component cascade reaction of polyyne oligomers with TCNE and tetrathiafulvalene (TTF). In most cases, the resulting chromophores feature intense intramolecular charge-transfer bands extending far into the near infrared region and some of them display high third-order optical nonlinearities. Despite substitution with strong donors, the electron-withdrawing moieties in the new chromophores remain potent acceptors and a number of them display positive first reduction potentials (vs. the ferrocenium/ferrocene (Fc(+)/Fc) couple in CH(2)Cl(2)), which rival those of parent TCNE, TCNQ and F(4)-TCNQ. The non-planarity of the chromophores strongly enhances their physical properties when compared to planar push-pull analogues. They feature high solubility, thermal stability and sublimability, which enables formation of amorphous, high-optical-quality thin films by vapour phase deposition and makes them interesting as advanced functional materials for novel opto-electronic devices.

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Section: Donor-substituted Expanded 7788-tetracyanoquinodimethanesmentioning

confidence: 99%

Non-planar push–pull chromophores

2010

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“…4 These chargetransfer complexes, based on reduced TCNQ, have attracted broad interest in view of their extensive and often novel electrical, 5,6 electrochemical, [7][8][9] spectroscopic properties, [10][11][12] potential applications in erasable photochromic laser disks and memory storage, [13][14][15] organic field-effect transistors, [16][17][18] biosensors, [19][20][21] conducting 1,4,22 and magnetic properties. [23][24][25][26][27][28][29][30][31][32] In terms of structure, magnetism and electric-field-induced behavior, the most noticeable example is the TCNQ lanthanide complex {[Gd 2 (TCNQ) 5 (H 2 O) 9 ][Gd(TCNQ) 4 (H 2 O) 3 ]}•4H 2 O behaving as a ferrimagnet. 33 Other representative TCNQ transition metal complexes [M(TCNQ)bpy] (M = Fe(II), Zn(II), Mn(II), Co(II), Cd(II), bpy = 4,4′-bipyridyl) are of a 3D network structure which exhibits metal-dependent guest-responsive color changes and electronic properties.…”

Section: Introductionmentioning

confidence: 99%

Three alkaline-earth metal complexes with 3D networks constructed from a 7,7,8,8-tetracyanoquinodimethane ligand: synthesis, structure and electrochemical properties

Yan

Hou

et al. 2013

Dalton Trans.

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Three new 7,7,8,8-tetracyanoquinodimethane (TCNQ) alkaline-earth metal complexes, namely {[M2(TCNQ)3(H2O)6]·TCNQ}n (M = Ca (1), Sr (2) and Ba (3)) have been synthesized by salt elimination reactions. X-ray crystallographic analysis reveals that complexes 1, 2 and 3 are isomorphic featuring a unique 3D structure. Cyclic and differential pulse voltammograms for complexes 1-3 show a reversible one-electron oxidation and a reversible one-electron reduction within the electrochemical window of CH3CN. Their electrochemical HOMO-LUMO gap and reversibility are examined.

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Two 7,7,8,8-tetracyanoquinodimethane lead and zinc complexes featuring 3D and 0D structure: Synthesis, structure and electrochemical properties

Wang

Yan

et al. 2014

Inorganica Chimica Acta

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Isolation of p-tricyanovinylphenyldicyanomethide ion via a [2+2] cycloaddition of 7,7,8,8-tetracyanoquinodimethane (TCNQ) molecules

Cited by 7 publications

References 34 publications

Non-planar push–pull chromophores

Non-planar push–pull chromophores

Three alkaline-earth metal complexes with 3D networks constructed from a 7,7,8,8-tetracyanoquinodimethane ligand: synthesis, structure and electrochemical properties

Two 7,7,8,8-tetracyanoquinodimethane lead and zinc complexes featuring 3D and 0D structure: Synthesis, structure and electrochemical properties

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