X-ray diffraction study of the crystal structure of the π-molecular compound pyrene<sup>...</sup>pyromellitic dianhydride at 19 K

Herbstein, F. H.; Marsh, Richard E.; Samson, S.

doi:10.1107/s0108768193011668

Cited by 10 publications

(2 citation statements)

References 23 publications

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“…The close agreement between X-ray structure and the B3LYP/6-31++G** optimized geometry of isolated pyrene (Table ) provides the first evidence of the reliability of this level of theory. The pyrene singlet−triplet gap is 48.5 kcal/mol.…”

Section: Resultsmentioning

confidence: 62%

Theoretical Prediction of Benzyne-Like Species in Pyrene Diradicals

et al. 2004

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The different products that can be obtained from pyrene dehydrogenation have been studied by means of hybrid density functional theory. Most of the didehydrogenated species exhibit a diradical character. This is supported by the closeness between the geometry and energy of singlet and triplet states and the open-shell nature of the singlet state. However, three didehydrogenated species have been found to exhibit a closed-shell singlet electronic ground state. The analysis of the electronic structure, the formation energy of these didehydrogenated species, and their geometrical structure reveals that these three didehydrogenated species are better described as benzyne-like moieties; two of them are of o- and one of m-benzyne character. The two o-benzyne species have lower energies than the m-benzyne and are favored upon diradical formation. This interpretation is fully supported by the analysis of multiconfigurational wave functions and the order of stabilities confirmed by second-order multireference perturbation theory calculations. A possible implication of the reactivity of these benzyne-like species in asphaltene formation is discussed.

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Section: Resultsmentioning

confidence: 62%

Theoretical Prediction of Benzyne-Like Species in Pyrene Diradicals

et al. 2004

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“…We report in a companion paper (Herbstein, Marsh & Samson, 1994; HMS94) the determination of the crystal and molecular structure of PYRPMA at 19 K, the lowest temperature attainable with the present apparatus. The crystal structure of PYRPMA at 295 K has been redetermined by Allen, Boeyens & Levendis (1989) and described in terms of a model in which the pyrenes are statically disordered over three orientations.…”

Section: Introductionmentioning

confidence: 99%

X-ray diffraction study of the disorder-to-order transition at ~160 K in the π-molecular compound pyrene^...pyromellitic dianhydride

Herbstein¹,

Samson²

1994

Acta Crystallogr Sect B

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The crystal structure of pyrene...pyromellitic dianhydride [(C16H10:CIoH206); PYRPMA] has been studied over the range 300-19K, using the low-temperature accessory designed by Samson, Goldish & Dick [J. Appl. Cryst. (1980), 13, 425-432] for a four-circle diffractometer. Earlier results for the disordered and ordered structures [Herbstein & Snyman (1969). Philos. Trans. R. Soc. London Ser. A, 264, corresponding to the doubling of c and change of space group; the specific heat shows an anomalous increase over the range 120-155K, giving a A-type peak. These results show that the transition is second order with regard to Ehrenfest's criteria. PYRPMA is a co-elastic crystal and quantitative analysis shows a linear dependence of the squares of spontaneous strain and of normalized superlattice intensity on temperature; hence, in terms of Landau theory, the transition is tricritical. However, the excess specific heat cannot be explained entirely on this basis. The physical nature of the transition is discussed. PYRPMA is so far unique among the 7r-molecular compounds showing disorderto-order transitions in the solid state in that there is a doubling of one of the axes; all indications are, however, that it resembles the other examples in the sense that subtle intermolecular packing interactions (here between pyrenes and PMDAs) are the driving force i Experimental work performed while on sabbatical leave at Caltech.

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Unusual solvent effect of molecular charge transfer complexes: Stacking/non-stacking interaction revealed by characterization of structure and photophysical aspects

Samanta

Sanyal

Maity

et al. 2017

Journal of Luminescence

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X-ray diffraction study of the crystal structure of the π-molecular compound pyrene^...pyromellitic dianhydride at 19 K

Cited by 10 publications

References 23 publications

Theoretical Prediction of Benzyne-Like Species in Pyrene Diradicals

Theoretical Prediction of Benzyne-Like Species in Pyrene Diradicals

X-ray diffraction study of the disorder-to-order transition at ~160 K in the π-molecular compound pyrene^...pyromellitic dianhydride

Unusual solvent effect of molecular charge transfer complexes: Stacking/non-stacking interaction revealed by characterization of structure and photophysical aspects

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X-ray diffraction study of the crystal structure of the π-molecular compound pyrene...pyromellitic dianhydride at 19 K

Cited by 10 publications

References 23 publications

Theoretical Prediction of Benzyne-Like Species in Pyrene Diradicals

Theoretical Prediction of Benzyne-Like Species in Pyrene Diradicals

X-ray diffraction study of the disorder-to-order transition at ~160 K in the π-molecular compound pyrene...pyromellitic dianhydride

Unusual solvent effect of molecular charge transfer complexes: Stacking/non-stacking interaction revealed by characterization of structure and photophysical aspects

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X-ray diffraction study of the crystal structure of the π-molecular compound pyrene^...pyromellitic dianhydride at 19 K

X-ray diffraction study of the disorder-to-order transition at ~160 K in the π-molecular compound pyrene^...pyromellitic dianhydride