P. Zugenmaier, J. Duff, T. L. Bluhm: Crystal and Molecular Structures of Six Differently with Halogen Substituted Bis (benzylimido) perylene

Crystal Research and Technology

Cryst. Res. Technol. 35 (2000) 1095 - Abstract -

P. Zugenmaier, J. Duff*, T. L. Bluhm**

Institute of Physical Chemistry, Clausthal University of Technology, Clausthal-Zellerfeld, Germany
*Xerox Research Centre of Canada, Mississauga, Canada
**The Document Company Xerox, Webster, USA

Crystal and Molecular Structures of Six Differently with Halogen Substituted Bis (benzylimido) perylene

The structures of bis (3,5-dichlorobenzylimido) perylene, bis (3-chlorobenzylimido) perylene, bis (3-fluorobenzylimido) perylene, bis (3,5-difluorobenzylimido) perylene, bis (4-chlorobenzylimido) perylene, and bis (2,6-difluorobenzylimido) perylene were solved by single crystal analysis. The compounds crystallize in four different space groups, that is, in sequence of the compounds listed P-1, P-1, P2₁/a, C2/c, Pbcn, P2₁/n, respectively, although their chemical constitutions are very similar. The packing in different arrangements causes the twist of the benzene ring to differ with respect to the perylene ring and amounts to 111.4°, 112.3°, 98.6°, 105.1°, 80.3°, 72.0° for the sequence of compounds listed, respectively. The first two compounds crystallizing in space group P-1 are isomorphous in structure and exhibit the same dark blue color. The C-F bond distances lie between 1.36 and 1.38 Å, the C-Cl bond distances between 1.73 and 1.75 Å. For all six structures investigated the planes of two adjacent perylene skeleton planes are 3.43 to 3.50 Å apart and the tilt angles versus the shortest unit cell dimension lie between 20° and 45°.

Keywords: crystal structure, bis (halogen benzylimido) perylenes, pigments, -overlap, packing, photosensitive

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