We have synthesised some planar polycyclic compounds, in which unsubstituted aromatic rings are condensed with perfluorinated aromatic rings, and have carried out a combined X-ray diffraction and computational study to analyse their self-recognition behaviour in crystalline phases. We compare our results with the parent hydrocarbons and with other compounds that have a variable degree of fluorination. Whereas the molecular planes in crystals of hydrocarbons with mono- or difluorinated aromatic rings or of perfluorinated compounds arrange themselves in V-shaped configurations, our present results show that perfluorinated rings tend to stack over unsubstituted rings even when these two moieties coexist in a condensed system, producing crystalline materials with parallel molecular layers with the arene-perfluoroarene recognition pattern. Our analysis shows that the packing energy of all these crystals is dispersion-dominated and that coulombic terms are selective rather than quantitatively predominant in crystals with arene-perfluoroarene interactions. No compelling proof of a special role of CHF interactions has been found.
Synthesis, X-ray diffraction, and computational study of the crystal packing of polycyclic hydrocarbons featuring aroamtic and perfluoroaromatic rings condensed in the same molecule: 1,2,3,4-tetrafluoronaphthalene, -anthracene, and -phenanthrene / F. Cozzi, S. Bacchi, G. Filippini, T. Pilati, A. Gavezzotti. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 13:25(2007), pp. 7177-7184.
|Titolo:||Synthesis, X-ray diffraction, and computational study of the crystal packing of polycyclic hydrocarbons featuring aroamtic and perfluoroaromatic rings condensed in the same molecule: 1,2,3,4-tetrafluoronaphthalene, -anthracene, and -phenanthrene|
COZZI, FRANCO (Primo)
BACCHI, SERGIO (Secondo)
|Parole Chiave:||arenes ; crystal engineering ; fluoroaromatic synthesis ; intermolecular interactions ; PIXEL calculations|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2007|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/chem.200700267|
|Appare nelle tipologie:||01 - Articolo su periodico|