Orientational disorder in phenanthrene. Structure determination at 248, 295, 339 and 344 K

Petřı́ček, V.; Cı́sařová, Ivana; Hummel, L.; Kroupa, J.; Březina, B.

doi:10.1107/s0108768190007510

Cited by 57 publications

(8 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structure of the ambient-temperature phase, monoclinic, space group P2 1 [form (II)], was first determined by Basak (1950) and later by Kay et al (1971) and Petříček et al (1990).…”

Section: Phenanthrenementioning

confidence: 99%

“…Phenanthrene undergoes a reversible phase transition at 339-344 K that was first discovered by Ueberreiter & Orthmann (1950) and subsequently studied by Kroupa et al (1988). The structure of the high-temperature phase, monoclinic, space group P2 1 /a, here denoted as form (I), was elucidated by Petříček et al (1990), who showed that the transition gives an orientationally disordered phase with approximately equal occupancies (55:45) of the two orientations. The hightemperature phase can be quenched by rapid cooling to 248 K.…”

Section: Phenanthrenementioning

confidence: 99%

See 1 more Smart Citation

Exploration of the high-pressure behaviour of polycyclic aromatic hydrocarbons: naphthalene, phenanthrene and pyrene

Fabbiani

Allan

Parsons

et al. 2006

Acta Crystallogr B Struct Sci

102

112

View full text Add to dashboard Cite

The structural response of three members of the family of polycyclic aromatic hydrocarbons (PAHs) to high-pressure recrystallization from dichloromethane solutions is presented. Recrystallization of naphthalene in the 0.2-0.6 GPa pressure range does not result in the formation of a new polymorph. Furthermore, direct compression of a single crystal to 2.1 GPa does not result in a phase transition. A density decrease of 18.2% over the 0.0-2.1 GPa pressure range is observed and the principal effect of pressure is to ;tighten' the herringbone structural motif and decrease the size of void regions. A new polymorph of pyrene, form III, has been crystallized at 0.3 and at 0.5 GPa. Structural investigation of this new polymorph by means of topological analysis and comparison of Hirshfeld surfaces and fingerprint plots shows that intermolecular interactions are substantially different from those found in the ambient-pressure structures, and do not fit a previously established packing model for PAHs. Similar discrepancies are found for the high-pressure polymorph of phenanthrene, which is here re-investigated in greater detail. The structures of these high-pressure polymorphs are dominated by pi...pi stacking with a limited contribution from C-H...pi (peripheral) interactions. It is perhaps not surprising that high-pressure polymorphs deviate from a model that has been devised for ambient-pressure structures, and this may be a direct consequence of the ability of pressure to modify and combine intermolecular interactions in ways that are not usually found at ambient pressure. This is achieved by modifying the relative orientations of molecules and by encouraging the formation of denser structures in which molecules pack together more efficiently.

show abstract

“…The structure of the ambient-temperature phase, monoclinic, space group P2 1 [form (II)], was first determined by Basak (1950) and later by Kay et al (1971) and Petříček et al (1990).…”

Section: Phenanthrenementioning

confidence: 99%

Section: Phenanthrenementioning

confidence: 99%

Exploration of the high-pressure behaviour of polycyclic aromatic hydrocarbons: naphthalene, phenanthrene and pyrene

Fabbiani

Allan

Parsons

et al. 2006

Acta Crystallogr B Struct Sci

102

112

View full text Add to dashboard Cite

show abstract

“…imum in the "lambda transition" peak. Petříček et al [14] found a phase transition in the temperature interval 333-343 K using X-ray diffraction. Arndt and Damask [13] observed a phase transition in the temperature range 333-348 K using DSC.…”

Section: Resultsmentioning

confidence: 99%

A similarity variable for estimating the heat capacity of solid organic compounds

Laštovka

Fulem

Becerra

et al. 2008

Fluid Phase Equilibria

View full text Add to dashboard Cite

“…[25][26][27] The C=C bond lengths of the quinoline (1.350-1.423 Å) and phenanthrene (1.336-1.468 Å) groups are very close to those reported for substituted quinoline (1.344-1.421 Å) and phenanthrene (1.338-1.454 Å) rings. 26,28 Compounds 1a and 1b were investigated by UV-Vis and fluorescence spectroscopy in order to evaluate their electronic properties. The obtained spectroscopic data are summarised in Table 2 and the corresponding spectra in CH 2 Cl 2 are shown in Figs 3 and 4.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Crystal Structures and Properties of 1,8-Di(Quinol-2-yl)Octa-1,7-Diyne and 1,8-di(Phenantren-9-yl)Octa-1,7-Diyne

Otero

Vera

León

et al. 2015

Journal of Chemical Research

View full text Add to dashboard Cite

1,8-Di(quinol-2-yl)octa-1,7-diyne and 1,8-di(phenanthren-9-yl)octa-1,7-diyne were synthesised by conventional and microwaveassisted methods in good yields. Microwave irradiation enhances the rate of these reactions. Photophysical properties of these derivatives were also evaluated, and it was found that 1,8-di(phenanthren-9-yl)octa-1,7-diyne displays a higher fluorescence quantum yield than 1,8-di(quinol-2-yl)octa-1,7-diyne. The molecular structures of 1,8-di(quinol-2-yl)octa-1,7-diyne and 1,8-di(phenanthren-9-yl)octa-1,7-diyne were established by single-crystal X-ray diffraction studies.

show abstract

Orientational disorder in phenanthrene. Structure determination at 248, 295, 339 and 344 K

Cited by 57 publications

References 3 publications

Exploration of the high-pressure behaviour of polycyclic aromatic hydrocarbons: naphthalene, phenanthrene and pyrene

Exploration of the high-pressure behaviour of polycyclic aromatic hydrocarbons: naphthalene, phenanthrene and pyrene

A similarity variable for estimating the heat capacity of solid organic compounds

Synthesis, Crystal Structures and Properties of 1,8-Di(Quinol-2-yl)Octa-1,7-Diyne and 1,8-di(Phenantren-9-yl)Octa-1,7-Diyne

Contact Info

Product

Resources

About