An x-ray structural study of N,N? (trans)-dimethylquinacridone

Zavodnik, V. E.; Chetkina, L. A.; Val'kova, G. A.

doi:10.1007/bf00746457

Cited by 12 publications

(17 citation statements)

References 4 publications

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“…Our results are basically in good agreement with those of Zavodnik et al (1981). The molecule is entirely planar, as shown in Fig.…”

Section: Commentsupporting

confidence: 90%

“…The crystal structure of the title compound, (I), was reported not only by Zavodnik et al (1981) but also by Ohmasa & Susse (1976). The present paper provides some additional results at 223 K with higher precision.…”

Section: Commentmentioning

confidence: 81%

“…The structure of the title compound, C 22 H 16 N 2 O 2 commonly called trans-N,N H -dimethylquinacridone, has been reinvestigated at 223 K [the original determination was by Zavodnik, Chetkina & Val'kova (1981). Zh.…”

mentioning

confidence: 99%

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Reinvestigation of 5,12-dihydro-5,12-dimethylquino[2,3-b]acridine-7,4-dione

Mizuguchi

Senju

2003

Acta Cryst E

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“…Our results are basically in good agreement with those of Zavodnik et al (1981). The molecule is entirely planar, as shown in Fig.…”

Section: Commentsupporting

confidence: 90%

Section: Commentmentioning

confidence: 81%

See 1 more Smart Citation

Reinvestigation of 5,12-dihydro-5,12-dimethylquino[2,3-b]acridine-7,4-dione

Mizuguchi

Senju

2003

Acta Cryst E

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“…The deformation of the bottom benzene ring can be attributed to the strain of the distorted structure, which drags the central benzene ring towards the acridone moiety through the four newly formed C−C bonds. The strain also makes the bond length of C−N (1.37–1.38 Å) shorter than that of N ‐phenylacridone (1.39 Å) . The lengths of the four newly formed C−C bonds are in the range of 1.48–1.50 Å, which are longer than that of the corresponding bond in indoloacridine derivatives (1.42–1.46 Å) .…”

Section: Figurementioning

confidence: 96%

A Nanoboat with Fused Concave N‐Heterotriangulene

Zhou

Zhang

2020

Angewandte Chemie

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The surface extension of all‐carbon based bowl‐shaped molecules, such as corannulene and sumanene, to synthesize even larger buckybowls has been widely studied, leaving other concave compounds with heteroatoms less considered. Herein we present a highly curved molecule synthesized via stepwise cyclization of fjords of a bisacridone derivative. Crystallographic analysis unambiguously confirmed a boat‐shaped structure with deformed bottom benzene ring. Theoretical calculation unravels an inversion process with an S‐shaped transition structure rather than a planar one. The enlarged boat demonstrates interesting properties, such as red shifts in absorption and emission spectra, enhanced emission intensity, and convergent frontier molecular orbital energy levels, in comparison to the related concave N‐heterotriangulene.

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“…Based on the reorganization energy, transfer integral and the center‐of‐mass distance, the hole and electron mobilities of acridone derivatives are calculated by setting the temperature at 300 K. The hole and electron mobilities of the parent N ‐phenylacridone BB‐Ph are estimated to be 0.35 cm 2 V –1 s –1 and 0.0006 cm 2 V –1 s –1 , respectively, according to its crystal packings . When more benzene rings are fused to acridone, the mobility varies according to the molecular shape and N ‐substituents.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure and Properties of Fused π‐Extended Acridone Derivatives

Gao

Zhang

2020

Eur J Org Chem

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Benzene‐ and naphthalene‐fused acridone derivatives with hexyl and phenyl groups at the amino position were synthesized and their properties were investigated experimentally and computationally. All the structures of these fused π‐extended acridone derivatives were unambiguously confirmed by single‐crystal X‐ray analysis, which revealed the presence of face‐to‐face π–π stackings along the acridone moiety and the intermolecular hydrogen bond‐directed molecular packings of the phenyl‐substituted acridone derivatives in the crystals. Moreover, the dimerization of linearly fused acridone derivative was observed after storing the crystals over months. The benzene ring at the turning point of the angularly fused acridone derivatives contained relatively longer and shorter C–C bonds, which affected the molecular conjugation, as confirmed by the results of photophysical characterization and the study of the aromaticity. Mobility calculations based on the molecular packings in the single crystals showed that the linearly fused acridone derivatives bearing better electron and hole mobilities are good candidates of organic functional materials.

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An x-ray structural study of N,N? (trans)-dimethylquinacridone

Cited by 12 publications

References 4 publications

Reinvestigation of 5,12-dihydro-5,12-dimethylquino[2,3-b]acridine-7,4-dione

Reinvestigation of 5,12-dihydro-5,12-dimethylquino[2,3-b]acridine-7,4-dione

A Nanoboat with Fused Concave N‐Heterotriangulene

Synthesis, Structure and Properties of Fused π‐Extended Acridone Derivatives

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