New organic ‘metals’: naphthaceno[5,6-cd:11,12-c′d′]bis[1,2]dithiolium iodides

Buravov, L. I.; Зверева, Г. И.; Kaminskii, V. F.; Rosenberg, Lisa; Khidekel, M. L.; Shibaeva, R. P.; Shchegolev, I. F.; Yagubskii, Eduard B.

doi:10.1039/c39760000720

Cited by 32 publications

(6 citation statements)

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“…No crystal structure of any oligoacene cation with more than three fused benzene rings has ever been reported. To confer stability on these larger systems, apparently substantial substituents are needed. − We therefore can apply the maximin principle to predict the stacking geometry of crystalline oligoacene cations (holes).…”

Section: Resultsmentioning

confidence: 99%

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The Maximin Principle of π-Radical Packings

et al. 2005

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A two-term model is proposed for hydrocarbon and N-containing pi-radicals which are in close contact with one another. The first term is attractive (due to partially occupied frontier pi-orbitals), and the second, repulsive (due to hard-core repulsion between close-lying atoms). This model is applied to dimers where intermolecular contacts are closer than <0.95 x the sum of the atomic van der Waals radii. The maximin principle is proposed. The maximin principle states that the lowest energy conformation maximizes overlap of the frontier orbitals while simultaneously minimizing intermolecular contacts. A Hückel Hamiltonian, the mu(2)-Hamiltonian, which contains the above attractive and repulsive terms, is applied. The interaction surfaces of two pi-hydrocarbon radical cations were calculated for the three systems known crystallographically to contain cations in close contact: naphthalene, fluoranthene, and pyrene. The global minima of these surfaces correspond to the experimentally determined structures. The mu(2)-Hamiltonian energy surfaces of the naphthalene cation dimer are qualitatively similar to those calculated at the RHF/6-311G(d,p) and MP2/6-311G(d,p) levels. The maximin principle is applied to N-containing pi-radicals. Except in the case of tetracyanoethene, the maximin principle correctly predicts the most common dimer crystal packing. (MgPc)(NO(3)).0.5THF and (MgPc)(ReO(4)).1.5THF (Pc = phthalocyanine) were prepared: both new crystal structures follow the maximin principle. The maximin principle is used to suggest the dimer cation ground state of oligoacenes, cations important as organic hole-based semiconductors.

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Section: Resultsmentioning

confidence: 99%

“…To confer stability on these larger systems, apparently substantial substituents are needed. [114][115][116][117][118][119] We therefore can apply the maximin principle to predict the stacking geometry of crystalline oligoacene cations (holes).…”

Section: Tcnq and Dcnqimentioning

confidence: 99%

The Maximin Principle of π-Radical Packings

et al. 2005

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“…dimensional organic metal, 118 due to its trains of interacting triiodides, and features a reported electrical conductivity close to that of elemental In. 22 Despite intense scientific consideration in the late 70s and early 80s, as testified by the 12 CSD depositions (TETTRI to TETTRI12) and related publications, [118][119][120][121][122] it was not possible, to the best of our knowledge, to fully elucidate the structure of the I 3 − trains, a fact that was, to some extent, also viewed as a consequence of the limited I-I bond localization of the interacting triiodides.…”

Section: Polyiodide Frameworkmentioning

confidence: 99%

Words in supramolecular chemistry: the ineffable advances of polyiodide chemistry

Savastano

2021

Dalton Trans.

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“…42,90,100–102 However, such TTF-based OSCs are usually difficult to maintain long-term air stability due to their low ionisation potential of about 4.8 eV. 103–106 Meanwhile, highly conducting CT complexes/salts have been reported even for non-TTF-type donors, such as perylene 107–112 and fluoranthene, 113–116 dithiapyrene, 117–123 and chalcogen-bridged acenes, 124–136 but the transistor properties of these donors are still limited. 137–144 This section describes a new class of non-TTF-based organic conductors derived from high-performance OSC materials.…”

Section: Organic Conductors Based On Organic Semiconductorsmentioning

confidence: 99%