Synthesis of electrically conductive organic solids

Wheland, Robert C.; Gillson, J.L.

doi:10.1021/ja00429a030

Cited by 312 publications

(122 citation statements)

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“…No definite reason for the discrepancy can be given, as the paper by Wheland and Gillson (4) gives no details as to experimental conditions under which voltammetry was performed. However, we suspect that the species formed by the oxidation process at +0.90 V reacted rapidly with a nucleophile in their solutions, and the likelihood of the reactant's being trace water will emerge from the discussion below.…”

Section: Resultsmentioning

confidence: 99%

Redox properties of 2,3,7,8-tetramethoxyselenanthrene: a charge-transfer donor

Addison¹,

Li²,

Weiler³

1977

Can. J. Chem.

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The redox properties of 2,3,7,8-tetramethoxyselenanthrene and 2,3,7,8-tetramethoxythianthrene have been studied in solution in order to compare their potential applicability as charge-transfer donors. The selenium compound is the weaker reductant, yielding a stable radical cation and a reactive dication, the former dimerizing in solution. Electron spin resonance and visible absorption spectra of the stable species were obtained. The 1:1 charge-transfer complexes of the above donors with tetracyanoquinodimethane are found to be insulators.

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Section: Resultsmentioning

confidence: 99%

Redox properties of 2,3,7,8-tetramethoxyselenanthrene: a charge-transfer donor

Addison¹,

Li²,

Weiler³

1977

Can. J. Chem.

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“…This is on the same order of magnitude as the two-probe pellet conductivity of some of the best organic conductors, 35 including the iconic TTF-TCNQ (σ pellet = 10 Scm -1 ). 36 Furthermore, the bulk conductivity of Ni 3 (HITP) 2 is one order of magnitude higher than that of the best s-MOG (Nihexathiobenzene, σ = 0.15 Scm -1 ), and at least 2 orders of magnitude better than the most conducting MOFs to date. [37][38][39] Even more remarkable results were obtained for thin films, configurations that are likely more relevant for future devices.…”

mentioning

confidence: 97%

High Electrical Conductivity in Ni₃(2,3,6,7,10,11-hexaiminotriphenylene)₂, a Semiconducting Metal–Organic Graphene Analogue

et al. 2014

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Reaction of 2,3,6,7,10, in aqueous NH 3 solution under aerobic conditions produces Ni 3 (HITP) 2 (HITP = 2,3,6,7,10,, a new two-dimensional metal−organic framework (MOF). The new material can be isolated as a highly conductive black powder or dark blue-violet films. Two-probe and van der Pauw electrical measurements reveal bulk (pellet) and surface (film) conductivity values of 2 and 40 S•cm −1 , respectively, both records for MOFs and among the best for any coordination polymer.

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“…Both organic complexes are characterized by CT parameters δ, 0.07 and 0.14, far from the 0.4-0.7 window in which metallic conductors are generally found [6], and are then very probably semiconductor materials or insulators. From this point of view, they are of little interest.…”

Section: Discussionmentioning

confidence: 99%

“…Although no far-reaching conclusions should be expected from this single parameter, it has been shown that δ is strongly related to the conductivity of the CT material: within the 0.4 < δ < 0.7 window, materials are promising candidates for organic metals [6]. If v1 is not available, for instance because no chemically stable ionic complex with δ = 1 can be synthesized, vibrational spectroscopy is still of interest, because closely related complexes may be compared.…”

Section: Introductionmentioning

confidence: 99%

Two Closely Related Organic Charge-Transfer Complexes Based on Tetrathiafulvalene and 9H-fluorenone Derivatives. Competition between Hydrogen Bonding and Stacking Interactions

Salmerón‐Valverde

Bernès

2015

Crystals

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Two 1:1 charge-transfer organic complexes were formed using tetrathiafulvalene as a donor and a 9H-fluorenone derivative as acceptor: 4,5,7-trinitro-9H-fluoren-9-one-2-carboxylic acid (complex 1) or 4,5,7-trinitro-9H-fluoren-9-one-2-carboxylic acid methyl ester (complex 2). Both systems crystallize with alternated donor and acceptor stacks. However, the crystal structure of 1 is influenced by classical hydrogen bonds involving carboxylic acid groups, which force to arrange acceptors as centrosymmetric dimers in the crystal, via R 2 2 (8) ring motifs, while such a restriction is no longer present in the case of 2, affording thus a different crystal structure. This main difference is reflected in stacking interactions, and, in turn, in the degree of charge transfer observed in the complexes. The degree of charge transfer, estimated using Raman spectroscopy, is δ 1 = 0.07 for 1 and δ 2 = 0.14 for 2. It thus seems that, at least for the studied complexes, hydrogen bonding is an unfavorable factor for charge transfer.

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Synthesis of electrically conductive organic solids

Cited by 312 publications

References 3 publications

Redox properties of 2,3,7,8-tetramethoxyselenanthrene: a charge-transfer donor

Redox properties of 2,3,7,8-tetramethoxyselenanthrene: a charge-transfer donor

High Electrical Conductivity in Ni₃(2,3,6,7,10,11-hexaiminotriphenylene)₂, a Semiconducting Metal–Organic Graphene Analogue

Two Closely Related Organic Charge-Transfer Complexes Based on Tetrathiafulvalene and 9H-fluorenone Derivatives. Competition between Hydrogen Bonding and Stacking Interactions

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Synthesis of electrically conductive organic solids

Cited by 312 publications

References 3 publications

Redox properties of 2,3,7,8-tetramethoxyselenanthrene: a charge-transfer donor

Redox properties of 2,3,7,8-tetramethoxyselenanthrene: a charge-transfer donor

High Electrical Conductivity in Ni3(2,3,6,7,10,11-hexaiminotriphenylene)2, a Semiconducting Metal–Organic Graphene Analogue

Two Closely Related Organic Charge-Transfer Complexes Based on Tetrathiafulvalene and 9H-fluorenone Derivatives. Competition between Hydrogen Bonding and Stacking Interactions

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High Electrical Conductivity in Ni₃(2,3,6,7,10,11-hexaiminotriphenylene)₂, a Semiconducting Metal–Organic Graphene Analogue