1,6,7,12,13,18-Hexaazatrinaphthylene tetrachloroform solvate

Abstract

The title compound, 1,6,7,12,13,18‐hexa­aza­tri­naphthyl­ene (HATN) tetra­chloro­form solvate, C24H12N6·4CH3Cl, belongs to a series of planar bridging ligands with an extensive delocalized π‐electron system. The planar mol­ecules pack in pairs with a π–π stacking of a symmetry‐related quinoline moiety and are surounded by solvent mol­ecules of chloro­form. The latter are involved in C—H⋯N contacts with the six pyrazine N atoms.

Synthesis, Ionisation Potentials and Electron Affinities of Hexaazatrinaphthylene Derivatives

“…Crystallographic data and details of the crystal structure solution and refinement are given in the Experimental Section, with complete information provided in the Supporting Information; the molecular structure is shown in Figure 1. As in the previously reported structures of the solvates of 1, [12,18] the molecules are essentially planar (mean deviation of the C and N atoms from the RMS molecular plane of 0.038 ) and, despite low crystallographic symmetry (C 1 ), molecules of 7 appear highly symmetrical, with approximate D 3h symmetry. Table 1 summarises the key bond lengths (averaged over chemically equivalent bonds for each structure), defined according to Figure 2, from the structures of two chloroform solvates of 1 [12,18,19] and from that of 7.…”

“…As in the previously reported structures of the solvates of 1, [12,18] the molecules are essentially planar (mean deviation of the C and N atoms from the RMS molecular plane of 0.038 ) and, despite low crystallographic symmetry (C 1 ), molecules of 7 appear highly symmetrical, with approximate D 3h symmetry. Table 1 summarises the key bond lengths (averaged over chemically equivalent bonds for each structure), defined according to Figure 2, from the structures of two chloroform solvates of 1 [12,18,19] and from that of 7. Also included in Table 1 are the corresponding bond lengths from density functional theory (DFT) calculations (B3 LYP/6-31G**) for the gas-phase molecules of 1, 6-9 and for the related model compounds benzene (I), pyrazine (II), triphenylene (III) and 1,4,5,8,9,12-hexaazatriphenylene (IV; Figure 2).…”

“…This p-stacking distance is somewhat shorter than seen in p-stacks of 1·CHCl 3 (3.48 ); [12] the structure of 1·4 CHCl 3 is quite different, with p-interactions within centrosymmetric dimers with an interplanar distance of 3.31 . [18] It is also rather short compared to the corresponding distance in many other p-stacked organic electronic materials, [36][37][38][39][40][41] including discotic columnar hexaazatrinaphthylene materials such as 3 a [6] and 4. [8] However, an equally short p-stacking distance of 3.18 has been reported in a high-carrier-mobility hydrogen-bonded hexaazatriphenylene-based columnar material.…”

“…Derivatives of 5,6,11,12,17,18-hexaazatrinaphthylene (diquinoxalino[3,3-a:2',3'-c]phenazine, 1) have recently attracted attention as materials for organic electronic applications. These compounds can, depending on the choice of substituent, form films with a wide range of morphologies, including crystalline, columnar discotic liquid-crystalline and amorAbstract: Several hexaazatrinaphthylene derivatives and a tris-A C H T U N G T R E N N U N G (thieno)hexaazatriphenylene derivative have been synthesised by reaction of the appropriate diamines with hexaketoA C H T U N G T R E N N U N G cyclohexane.…”

cis-(6RS,13RS)-3,3,10,10-Tetramethyl-6,13-diphenyl-1,8-dioxa-4,11-diazacyclotetradecane-2,5,9,12-tetraone and two of its precursors

“…This indicates that the pairwise intermolecular hydrogen-bonding interactions are quite strong. In such cases, some practitioners have described observations that suggest there may be a tendency for the hydrogen bonds to become more symmetrical, disordered across the OÁ Á ÁO vector, or even perfectly symmetrical (Gilli et al, 1994;Alfonso et al, 2001). The re®ned position of atom H2, at ®rst glance, seems to support the idea of partial symmetricalization of the H-atom position, but other evidence suggests that the re®ned position may be misleading.…”