The crystal structure of naphthaceno[5,6-cd:11,12-c'd']bis(1,2-dithiolane) (tetrathiotetracene)

Abstract

Tetrathiotetracene crystals belong to space group P1 with a= 9"890, b= 18.226, c= 3.968 A, 0~ = 87 ° 38', fl= 79°44 ', y=96°29 ' and two molecules per cell. The crystal structure has been determined by a threedimensional X-ray diffraction analysis. Intensity data were collected on photographic film and a Stoe diffractometer. The structure was solved from the Patterson functions (001) and (100) with the help of the Fourier technique and packing considerations. Refinement by a full-matrix, least-squares method gave a final R value of 0.13 for 1100 reflexions. The S-S bond length is 2"100 A, and the average S-C distance is 1.781 A. The molecule is nearly planar; only the S atoms are slightly out of the plane (0.021 to 0"056 ,~). The C-C bond lengths are almost the same as those in the tetracene molecule.

Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics

“…Structural aspects of one-dimensional conductors based on TTT were reviewed previously . Two structural modifications of TTT, orthorhombic and triclinic, were prepared as single crystals, while only the structure of the triclinic phase was completely established. , The X-ray structure of TSeT is also known . As π-donors, TTT and TSeT form a variety of conducting ion radical salts.…”

Chalcogenoarene semiconductors: new ideas from old materials

“…Compound 12 crystallizes in the P1 space group with two molecules per unit cell and with its backbone nearly planar with only S atoms slightly out of plane. 57 When viewed down the c-axis, the molecules are p-stacked (interplanar distance of 3.40 A ˚) in two nonequivalent stacks which are nearly vertical to each other (ca. 86 ) due to the occurrence of C-H/p intermolecular contacts (ca.…”

Synthesis and thermoelectric properties of 2- and 2,8-substituted tetrathiotetracenes

“…In particular, the closest intermolecular distances are C-H…Cipso contacts that range 2.94-2.95 Å In comparison, C-H…Cipso contacts are absent in a representative literature TTT (1a) X-ray crystal structure (CCDC code: NPDTOL). 8 The closest intermolecular interactions in this structure are between the S-S units and the phenylene units (S…C-H 3.45-3.68 Å) and between the disulfide units themselves (S-S…S-S 3.75-5.11 Å); leading to a greater tendency for face-face interaction ( Figure 1B). Attempts to attain single crystals of any of the TTT derivatives 1b-h have, thus far, been unsuccessful.…”