Syntheses, crystal structures and DFT calculations of 2-[4,5-bis(ethylsulfanyl)-1,3-dithiol-2-ylidene]-5- (4,5-diiodo-1,3-dithiol-2-ylidene)-1,3-dithiolan-4-thione and -one

The asymmetric unit of the title compound, C9H4S7, contains two independent molecules, in one of which the central five-membered ring is disordered over two orientations in a 0.924 (3):0.076 (3) ratio. The molecular skeleton is almost planar: the average distance of the atoms from their mean plane is 0.128 (7) Å in the ordered molecule, and 0.088 (5) and 0.123 (2) Å in the major and minor disorder components, respectively. The ordered and disordered molecules form separate columns by stacking along the b axis. Adjacent columns interact via short S⋯S [3.33 (2), 3.434 (3), 3.444 (2), 3.503 (2), 3.519 (3) and 3.53 (4) Å] and S⋯H [2.814 (2), 2.87 (7), 2.92 (2), 2.9269 (18), 2.93 (2), 2.94 (2), 2.939 (2), 2.967 (2) and 2.974 (1) Å] contacts.

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2,5-Bis(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione

Ueda

Suzuki

Kunimoto

et al. 2011

Acta Cryst E

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Syntheses, Crystal Structures and Solid-State Absorption Spectra of n-Propylsulfanyl- and Isopropylsulfanyl-Substituted 2,5-Di(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione Derivatives with Methoxycarbonyl Groups

Ueda¹,

Kusanagi²,

Nanbo³

et al. 2016

Bulletin of the Chemical Society of Japan

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N-propylsulfanyl and isopropylsulfanyl substituted 2,5-di(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione derivatives with methoxycarbonyl groups were synthesized, and their redox and electronic properties and crystal structures were investigated. Solid-state absorption spectra showed that both derivatives absorb almost all visible light. Furthermore isopropylsulfanyl-substituted derivatives absorb near-infrared light and the absorption edge reaches around 1320 nm. The crystal structures show that both derivatives are stacked in one dimension to form a columnar structure, but the molecular arrangements of their columns were quite different from each other. The stacked n-propylsulfanyl derivatives kept their orientation of thiocarbonyl groups in the same direction and the one molecule of the isopropylsulfanyl derivatives were rotated in relation to each other by an angle of 56° about their longer molecular axis. The TD-DFT calculation of stacked molecules suggests that the molecular arrangement among the stacked molecules affects the maximum absorption in near-infrared region.

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Syntheses, crystal structures and DFT calculations of 2-[4,5-bis(ethylsulfanyl)-1,3-dithiol-2-ylidene]-5- (4,5-diiodo-1,3-dithiol-2-ylidene)-1,3-dithiolan-4-thione and -one

Cited by 2 publications

References 32 publications

2,5-Bis(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione

2,5-Bis(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione

Syntheses, Crystal Structures and Solid-State Absorption Spectra of n-Propylsulfanyl- and Isopropylsulfanyl-Substituted 2,5-Di(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione Derivatives with Methoxycarbonyl Groups

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