Crystal and molecular structure of <i>s</i>-triphenyltriazine

Damiani, A.; Giglio, E.; Ripamonti, A.

doi:10.1107/s0365110x65003018

Cited by 25 publications

(16 citation statements)

References 1 publication

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“…Thus, no further counterion is found, and only two further molecules of benzonitrile are present as solvent of crystallization within the crystal structure. In accordance with the discussed oligomerizations of nitriles, the utilization of different transition metal chlorides within solvothermal reactions yield the same or similar nitrile "trimers": Upon reaction of benzonitrile with CoCl 2 in the presence of LiOH, free triphenyltriazine [24] is obtained in approximately 65 % yield and high crystallinity (see Scheme 4), whereas acetonitrile with VCl 3 in the presence of pyridine/LiOH as base yields trace amounts of [V(O)(C 2 N 3 H 3 ) 2 (py)]Cl 2 ·CH 3 CN (see Supporting Information). The reaction towards the latter two compounds probably proceeds according to the above-mentioned mechanisms.…”

Section: Resultssupporting

confidence: 63%

Solvothermal Reactions in and with Nitriles

2015

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Section: Resultssupporting

confidence: 63%

Solvothermal Reactions in and with Nitriles

2015

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“…A comparison of 8 d with 11 provides the valuable information that the planar structure of the central 2,4,6-triphenyl-1,3,5-triazine moiety in 8 d is very suitable for p stacking. The planar structure in 8 d was elucidated not only on the basis of the single-crystal structure of 2,4,6-triphenyl-1,3,5-triazine [20] but also by molecular modeling (Spartan, Hartree-Fock 6-31G*, Figure 10). Probably, the electron-deficient nature of the central triazine core contributes to the p-stacking interactions that stabilize the one-dimensional aggregate.…”

Section: Resultsmentioning

confidence: 99%

“…[19] The electron is conventionally transported along a suitable p-stacking path between the molecules even in the amorphous state. This p stacking is ascribed to the flat conformation of the central triphenyltriazine core, [20] which tends to form a columnar-type stacking path. [21] This result led us to design new p-stacked columnar-type architectures based on self-assembling triazine-based discotic molecules.…”

Section: Introductionmentioning

confidence: 99%

An Enantiomeric Nanoscale Architecture Obtained from a Pseudoenantiomeric Aggregate: Covalent Fixation of Helical Chirality Formed in Self‐Assembled Discotic Triazine Triamides by Chiral Amplification

Ishi‐i

Kuwahara

Takata

et al. 2006

Chemistry A European J

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Covalent fixation of a chiral helical structure which is created in a self-assembling system by a chiral-amplification method based on the sergeants/soldiers principle is reported. Disk-shaped triazine triamides self-assembled to form columnar-type helical aggregates through pi-stacking interactions among the central triphenyltriazine moieties, hydrogen-bonding interactions among the amide groups, and van der Waals interactions among the alkyl groups in nonpolar solvents such as hexane, octane, toluene, and p-xylene. When the achiral triazine triamide soldier component is mixed with a tiny amount of the chiral triazine triamide sergeant component, control of the intrinsic supramolecular helicity of the self-assembled soldier component by the sergeant component leads to chiral amplification and formation of a pseudoenantiomeric aggregate with only one handedness of the helix. The helicity can be preserved by ring-closing olefin metathesis polymerization mediated by Grubbs catalyst when an achiral component with terminal olefinic groups forms the pseudoenantiomeric aggregate in the presence of a tiny amount of the chiral component without olefinic groups. After polymerization and removal of the chiral component, the polymeric architecture obtained from the achiral soldier component is optically active and thus can be regarded as an enantiomeric object in which the chiral information transferred from the chiral sergeant component is preserved. The nanoscale chiral structure is fixed perfectly, as indicated by CD spectroscopic evidence obtained in a polar THF medium at high temperature and low concentration. AFM and TEM observations show a nanoscale fibrous structure with a diameter of 2-4 nm, which corresponds to the molecular size of the triazine triamide monomer.

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“…In anisaldehyde azine (Galign6 & Falgueirettes, 1968), lengths were (ph)C-C(H) 1.510, 1.480; (H)C=N 1.265, 1.300; N-N 1.410A. In s-triphenyltriazine (Damiani, Giglio & Ripamonti, 1965) there are six chemically identical C-N bonds of order 1-5 whose bond lengths range from 1.321 to 1.359 A, eighteen aromatic C-C bonds whose lengths range from 1.368 to 1.415 A and three (ph)C-C(sp 2) bonds: 1.465, 1.474, 1.485 A. It is evident that the probable error in all these bond lengths is between 0.01 and 0.02 A and there is no clear case for choosing any one of the C-C bonds as being more accurate than any other.…”

Section: (~)mentioning

confidence: 99%