Imidazolfarbstoffe III. Reaktion des sym-Tetraaminobenzols mit Carbonsäuren

Arient, J.; Marhan, J.; Täublová, H.

doi:10.1135/cccc19601602

Cited by 9 publications

(4 citation statements)

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“…Reduction of 2 − 4 with LiAlH 4 in THF followed by aerobic workup afforded the expected p -benzoquinonediimine ligands 5 − 7 , respectively. Although the preparation of 3 was mentioned in 1960, its full characterization was not reported . All compounds are stable in the solid state and in solution for several days at room temperature and in the presence of light.…”

Section: Resultsmentioning

confidence: 99%

Novel “Potentially Antiaromatic”, Acidichromic Quinonediimines with Tunable Delocalization of Their 6π-Electron Subunits

et al. 2003

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We present a novel family of "potentially antiaromatic" alkyl-substituted p-benzoquinonediimine pH-dependent chromophores. It appears from the structural data that these overall 12 pi-electron molecules should be better considered as constituted by two chemically connected but electronically not conjugated 6 pi-electron subunits. Molecule 5 appears to be the first example of two separated, conjugated, and localized 6 pi-electron systems that can be tuned by reversible protonation to become delocalized. The mono- and diprotonated derivatives have been characterized by spectroscopic methods and X-ray diffraction. These systems develop supramolecular interactions in the solid state that clearly reflect the degree of protonation and depend on the nature of the counterion. These compounds constitute new chromophores for which the color can be tuned depending on the degree of protonation, going in solution from yellow for 5 to red for 5.HCl and blue for 5.2HCl. Theoretical calculations have provided a deeper insight into the electronic structure of these molecules and allowed an assignment of the experimental UV-vis spectra. The visible and near-UV spectrum of the neutral and protonated benzoquinonediimines can be classically assigned from the coupling of two 6 pi-electron polymethine units. TD-DFT calculations confirm the observed red shift of the two lowest pi --> pi* transitions of the benzoquinonediimines upon protonation and relate it to the moderate energy lowering of the HOMO --> LUMO transition induced by the delocalization of the polymethine pi system.

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Section: Resultsmentioning

confidence: 99%

Novel “Potentially Antiaromatic”, Acidichromic Quinonediimines with Tunable Delocalization of Their 6π-Electron Subunits

et al. 2003

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“…Benzodiimidazole (DMBDIZ) was synthesized from 1,2,4,5benzentetramine, according to the literature procedure of Ariant et al (1960). The free ligand DMBDIZ and ZnCl 2 in 1 M hydrochloric acid were mixed and the resulting solution was allowed to stand at room temperature.…”

Section: Methodsmentioning

confidence: 99%

The complex salt benzodiimidazolium tetrachlorozincate

Cai

Tian

et al. 2002

Acta Cryst E

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“…Experimental DMDBIZ was synthesized from 1,2,4,5-benzenetetramine according to Arient et al (1960). 1,2,4,5-Benzenetetramine was synthesized from 2-dichlorobenzene by a three-step reaction (Cai, 2002).…”

Section: Commentmentioning

confidence: 99%

The mononuclear cobalt(II) complex Co^II(DMBDIZ)₂(NCS)₂, where DMBDIZ is 2,6-dimethylbenzo[1,2-d:4,5-d′]diimidazole

Cai

Tian

et al. 2002

Acta Crystallogr C

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In the title mononuclear cobalt complex, bis(2,6-dimethyl-1H,7H-benzo[1,2-d:4,5-d']diimidazole-kappaN(3))bis(thiocyanato-kappaN)cobalt(II), [Co(II)(NCS)(2)(DMBDIZ)(2)] or [Co(NCS)(2)(C(10)H(10)N(4))(2)], the cobalt(II) ion is coordinated to four N atoms, from two thiocyanate anions and two DMBDIZ ligands, in a distorted tetrahedral geometry. In the DMBDIZ ligand, the two imine N atoms are positioned cis with respect to one another. The crystal packing of the complex is dominated by both hydrogen bonding, involving two N-H...N and two N-H...S interactions, and aromatic pi-pi stacking.

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Imidazolfarbstoffe III. Reaktion des sym-Tetraaminobenzols mit Carbonsäuren

Cited by 9 publications

References 0 publications

Novel “Potentially Antiaromatic”, Acidichromic Quinonediimines with Tunable Delocalization of Their 6π-Electron Subunits

Novel “Potentially Antiaromatic”, Acidichromic Quinonediimines with Tunable Delocalization of Their 6π-Electron Subunits

The complex salt benzodiimidazolium tetrachlorozincate

The mononuclear cobalt(II) complex Co^II(DMBDIZ)₂(NCS)₂, where DMBDIZ is 2,6-dimethylbenzo[1,2-d:4,5-d′]diimidazole

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Imidazolfarbstoffe III. Reaktion des sym-Tetraaminobenzols mit Carbonsäuren

Cited by 9 publications

References 0 publications

Novel “Potentially Antiaromatic”, Acidichromic Quinonediimines with Tunable Delocalization of Their 6π-Electron Subunits

Novel “Potentially Antiaromatic”, Acidichromic Quinonediimines with Tunable Delocalization of Their 6π-Electron Subunits

The complex salt benzodiimidazolium tetrachlorozincate

The mononuclear cobalt(II) complex CoII(DMBDIZ)2(NCS)2, where DMBDIZ is 2,6-dimethylbenzo[1,2-d:4,5-d′]diimidazole

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The mononuclear cobalt(II) complex Co^II(DMBDIZ)₂(NCS)₂, where DMBDIZ is 2,6-dimethylbenzo[1,2-d:4,5-d′]diimidazole