Redetermination of the structure of phenanthridine

Brett, Waldemar A.; Rademacher, Paul; Boese, R.

doi:10.1107/s0108270193005062

Cited by 13 publications

(16 citation statements)

References 2 publications

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“…To our best knowledge, very little is known about the crystals of monoazaphenanthrenes. The crystal structure and the molecular structure of PHN have been determined [20], and subsequently redetermined [21] by X-ray diffraction. On the other hand, no crystallographic data concerning 7,8-benzoquinoline are available.…”

Section: Fluorescence Spectra and Their Temperature Dependencementioning

confidence: 99%

Spectroscopy and Photophysics of Monoazaphenanthrenes III. Luminescence of Phenanthridine and 7,8-benzoquinoline in Crystalline State

2004

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Fluorescence and phosphorescence spectra and the decay profiles of both these emissions have been investigated for the polycrystals of phenanthridine and 7,8-benzoquinoline, in the liquid helium (5 K) -room temperature range. These two monoazaderivatives of phenanthrene, which differ only by the position of N-heteroatom in the aromatic ring skeleton of phenanthrene, were found to exhibit very different fluorescence spectra, which also differ greatly in their temperature behavior. Supplementary investigations of the fluorescence of single crystals of 7,8-benzoquinoline have supported classification of observed fluorescence as an excimer fluorescence (caused by the specific arrangement of molecules of 7,8-benzoquinoline in the crystal). In contrary fluorescence of phenanthridine crystals is of the monomeric type. Phosphorescence spectra observed for the crystals of both molecules are very similar, but their temperature dependence is also different. This may be considered as an indication of a different physical mechanism of nonradiative intersystem crossing processes, which are operating between the lowest excited singlet state and the lowest excited triplet state in the crystals of both molecules.

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Section: Fluorescence Spectra and Their Temperature Dependencementioning

confidence: 99%

Spectroscopy and Photophysics of Monoazaphenanthrenes III. Luminescence of Phenanthridine and 7,8-benzoquinoline in Crystalline State

2004

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“…It would be logical to expect changes in bond lengths involving the N atom bonded covalently or coordinatively. In phenanthridine (Brett, Rademacher & Boese, 1993) C--N bond lengths are 1.296 (3) and 1.397 (3)/~ and the C--N---C bond angle is 117.8 (2) °. In (2) the phenanthridine N atom is not in the first coordination (Dietrich, Viout & Lehn, 1993) of the alkali atom, whereas in (3) the N atoms from both phenanthridine arms are coordinated to sodium.…”

Section: Molecular and Crystal Structuresmentioning

confidence: 99%

“…The initial (Brett, Rademacher & Boese, 1993) (maximum differences to the experimental values are 0.006/~ and 0.4 °), PM3 (maximum differences 0.005/~ and 0.9 °) and MM3 (maximum differences 0.007,~ and 0.4 ° ) were obtained. order of g (N50--C60) and three with g (C40A--N50, C60--C60A and C 10A0--C 10B0).…”

Section: Evaluation Of Cmc and C--n Bond Lengths Of Phenanthridine Bymentioning

confidence: 99%

“…The values of the C---C and C--N bond lengths of phenanthridine, obtained by X-ray structure determination (Brett, Rademacher & Boese, 1993), are compared with the calculated values using semi-empirical methods and molecular mechanics ( Table 8). The initial (Brett, Rademacher & Boese, 1993) (maximum differences to the experimental values are 0.006/~ and 0.4 °), PM3 (maximum differences 0.005/~ and 0.9 °) and MM3 (maximum differences 0.007,~ and 0.4 ° ) were obtained.…”

Section: Evaluation Of Cmc and C--n Bond Lengths Of Phenanthridine Bymentioning

confidence: 99%

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Bond length–bond order relations and calculated geometries for some benzenoid aromatics, including phenanthridine. Structures of 5,6-dimethylphenanthridinium triflate, [N-(6-phenanthridinylmethyl)-aza-18-crown-6-κ⁵ O,O',O'',O''',O''''](picrate-κ²-O,O')potassium, and [N,N'-bis(6-phenanthridinyl-κN-methyl)-7,16-diaza-18-crown-6-κ⁴ O,O',O'',O

Kiralj¹,

Kojić‐Prodić²,

Žinić³

et al. 1996

Acta Crystallogr Sect B

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The crystal structures of the title compounds are studied in order to investigate the role of novel fluoroionophores in complexation of sodium and potassium. In the potassium complex seven coordination, including the picrate ligand, is encountered. An additional coordination site is via the phenanthridine nitrogen at 3.252 (2)/~ (second coordination). The complex is of C1 symmetry and the aza-18-crown-6 macrocylic ring exhibits a crown-type conformation. The 7,16-diaza-18-crown-6 macrocycle accommodates a six-coordinate sodium with two additional ligands, via nitrogen from phenanthridine units. The complex cation shows a crystallographic twofold symmetry. The macrocycle is not of the crown-type conformation. In both complexes the alkali metals are shifted out of the cavity centres towards a picrate ligand in [N-(6-phenanthridinylmethyl

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“…effect is typical for angular annelated polycyclic compounds like phenanthrene (Kay, Okaya & Cox, 1971) or phenanthridine (Brett, Rademacher & Boese, 1993), but it is less pronounced and within 3tr in the title compound. In the annelated 2,5-dihydrothiophene rings the bond lengths are in the normal range of C(sp3)--S and C(sp3)--C(sp 2) single and C(sp:)--C(sp 2) double bonds (Rademacher, 1987), indicating that the annelation has no distinct effect on this part of the molecule.…”

Section: (4) C(8)--h(8b)---s(1a)mentioning
confidence: 99%

Structure of 1,3,6,8-tetrahydrodithieno[3,4-a:3',4'-c]benzene
Brett¹,
Rademacher²,
Boese³
1993
Acta Crystallogr C
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Redetermination of the structure of phenanthridine

Cited by 13 publications

References 2 publications

Spectroscopy and Photophysics of Monoazaphenanthrenes III. Luminescence of Phenanthridine and 7,8-benzoquinoline in Crystalline State

Spectroscopy and Photophysics of Monoazaphenanthrenes III. Luminescence of Phenanthridine and 7,8-benzoquinoline in Crystalline State

Structure of 1,3,6,8-tetrahydrodithieno[3,4-a:3',4'-c]benzene

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