The structures of some charge-transfer complexes containing TCNQ as acceptor and their electrical anisotropy

Zöbel, Dieter; Ruban, Gennady I.

doi:10.1107/s0108768183003092

Cited by 22 publications

(24 citation statements)

References 15 publications

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“…A degree of charge transfer (δ) of only ca. 10% was estimated on the basis of the change in the bond lengths of the TCNQ molecule between the neutral and the anion radical state 3 ORTEP view of the complex 3-TCNQ .…”

Section: Resultsmentioning

confidence: 99%

Effect of Structural Factor on the Electropolymerization of Bithiophenic Precursors Containing a 3,4-Ethylenedisulfanylthiophene Unit

et al. 2005

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A series of bithiophenes based on bis(3,4-alkylenedisulfanylthiophene) and hybrid systems associating 3,4-ethylenedisulfanylthiophene (EDST) with thiophene or 3,4-ethylenedioxythiophene (EDOT) moieties have been synthesized. The molecular structures of these systems are characterized by X-ray diffraction and theoretical geometric optimization. Although bis(alkylenesulfanylthiophenes) present a large dihedral angle between the thiophene cycles, for the hybrid systems the steric hindrance to coplanarity is counterbalanced by the development of intramolecular S···S and S···O interactions. Dramatic structural change from twisted to planar conformation of bis(3,4-ethylenedisulfanylthiophene) is observed when the dimer is associated with TCNQ. The electronic properties of the dimers, analyzed by UV−vis spectroscopy, cyclic voltammetry, and theoretical calculations, are discussed in relation with the molecular structure of the bithiophenes. Finally, the analysis of the electrogenerated polymers confirm the key role of the electronic and self-structuring effects for enhancing the planarity of the conjugated systems and for controlling the gap of the polymers. Thus, the precursor combining EDST and EDOT units shows the lowest oxidation potential and leads to a polymer presenting a lower band gap than those of the two polymers derived from the pure EDOT or EDST dimers.

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Section: Resultsmentioning

confidence: 99%

Effect of Structural Factor on the Electropolymerization of Bithiophenic Precursors Containing a 3,4-Ethylenedisulfanylthiophene Unit

et al. 2005

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“…In particular, static and dynamical disorders are known to play a significant role in the structure and properties of stilbenecontaining compounds. Single-crystal XRD measurements of neat STB and the CT complex STB-TCNQ show that the STB molecule can adopt two orientations that are related to one another by a twofold rotation about the longest molecular axis [45][46][47] . The librational motion responsible for the interconversion between these two conformers can be viewed as a rotation of the central C ¼ C stilbene moiety at fixed orientation of the benzene rings relative to the crystal lattice and is referred to as a pedal-like (crankshaft) motion.…”

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confidence: 99%

Freezing-in orientational disorder induces crossover from thermally-activated to temperature-independent transport in organic semiconductors

et al. 2014

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The crystalline structure of organic materials dictates their physical properties, but while significant research effort is geared towards understanding structure-property relationships in such materials, the details remain unclear. Many organic crystals exhibit transitions in their electrical properties as a function of temperature. One example is the 1:1 chargetransfer complex trans-stilbene-2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane. Here we show that the mobility and resistivity of this material undergo a transition from being thermally activated at temperatures above 235 K to being temperature independent at low temperatures. On the basis of our experimental and theoretical results, we attribute this behaviour to the presence of a glass-like transition and the accompanied freezing-in of orientational disorder of the stilbene molecule.

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“…While DTT has been extensively used in covalently linked donor-acceptor architectures [14,15,24], there is a single example charge-transfer (CT) complex with DTT as a donor and 7,7,8,8-tetracyanoquinodimethane (TCNQ) as an acceptor described in 1983 [27]. Here, we report the X-ray single crystal analysis of the DTT and its mixed-stack complexes with trimeric perfluoroo-phenylene mercury (I) (Chart 1), an acceptor known to form mixed-stack co-crystals with a variety of donors [28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Castañeda

Khrustalev

Fonari

et al. 2015

Journal of Molecular Structure

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The structures of some charge-transfer complexes containing TCNQ as acceptor and their electrical anisotropy

Cited by 22 publications

References 15 publications

Effect of Structural Factor on the Electropolymerization of Bithiophenic Precursors Containing a 3,4-Ethylenedisulfanylthiophene Unit

Effect of Structural Factor on the Electropolymerization of Bithiophenic Precursors Containing a 3,4-Ethylenedisulfanylthiophene Unit

Freezing-in orientational disorder induces crossover from thermally-activated to temperature-independent transport in organic semiconductors

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

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