Journal ArticleDOI
Molecular Semiconductors from Bifunctional Dithia- and Diselenadiazolyl Radicals. Preparation and Solid-State Structural and Electronic Properties of 1,4-[(E2N2C)C6H4(CN2E2)] (E = S, Se)
A. Wallace Cordes,Robert C. Haddon,Richard T. Oakley,Lynn Schneemeyer,Joseph V. Waszczak,Kelly M. Young,Neil M. Zimmerman +6 more
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In this paper, the 1,4-phenylene bis(dithiadiazolium) and bis(diselenadiazolinium) dichlorides were shown to be monoclinic, space group P2{sub 1}/n.Abstract:
The reactions of 1,4-phenylenebis(N,N,N{prime}-tris(trimethylsilyl)amidine) with sulfur and selenium dichlorides yield, respectively, the 1,4-phenylenebis(dithiadiazolium) and bis(diselenadiazolium) dichlorides 1,4-((E{sub 2}N{sub 2}C)C{sub 6}H{sub 4}(CN{sub 2}E{sub 2}))Cl{sub 2} (E = S, Se). Reduction of these materials with triphenylantimony affords the corresponding diradical species 1,4-((E{sub 2}N{sub 2}C)C{sub 6}H{sub 4}(CN{sub 2}E{sub 2})), which can be purified by high vacuum sublimation. The crystal structures of 1,4-((E{sub 2}N{sub 2}C)C{sub 6}H{sub 4}(CN{sub 2}E{sub 2})) (E = S, Se) are both monoclinic, space group P2{sub 1}/n. The crystal packing consists of sheets of interleaved columns of weakly associated diradical units (dimers); the mean intradimer separation is 3.34/3.37 {angstrom} (E = S/Se). The sulfur compound is an insulator, but the selenium material has a room temperature pressed pellet resistivity of about 100 {Omega} cm. Magnetic susceptibility measurements show the solids to be predominantly diamagnetic with variable amounts of paramagnetic defects in the lattice. While the exact mechanism of conduction remains to be established, these systems represent the first structurally characterized conducting materials constructed from neutral molecular radicals.read more
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Development of Conductive Organic Molecular Assemblies: Organic Metals, Superconductors, and Exotic Functional Materials
Gunzi Saito,Yukihiro Yoshida +1 more
TL;DR: In this paper, the development of conductive organic molecular assemblies including organic metals, superconductors, single component conductors, conductive films, and conductive liquids was introduced.
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Thiazyl radicals: old materials for new molecular devices
TL;DR: In this paper, a review describes recent advances in the development of thiazyl radicals, particularly dithiadiazolyl (RCNSSN), as molecule-based materials.
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The first phenalenyl-based neutral radical molecular conductor
X. Chi,Mikhail E. Itkis,Brian O. Patrick,Tosha M. Barclay,Robert W. Reed,Richard T. Oakley,A. W. Cordes,Robert C. Haddon +7 more
TL;DR: In this paper, the authors report the preparation, crystallization, and solid-state characterization of a spiro-biphenalenyl radical and show that it is monomeric in the solid state.
Journal ArticleDOI
Pancake Bonding: An Unusual Pi-Stacking Interaction.
TL;DR: The role of van der Waals interactions in pancake bonded dimers, chains, and other aggregates is different from closed shell vdW aggregates: here the Pauli repulsions reduce the attractive dispersion interaction significantly.
Journal ArticleDOI
Band electronic structure of one- and two-dimensional pentacene molecular crystals
Robert C. Haddon,Xiaoliu Chi,Mikhail E. Itkis,John E. Anthony,DL Eaton,Theo Siegrist,CC Mattheus,Ttm Palstra +7 more
TL;DR: In this article, the EHT calculations of the band electronic structure of substituted pentacene derivatives and the polymorphs of the parent compound were performed and the results showed that there are wide disparities among the bandwidths and electronic dimensionalities of these compounds.