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Arene-perfluoroarene interactions in crystal engineering: structural preferences in polyfluorinated tolans

Lookup NU author(s): Dr Caroline Bridgens, Dr Edward Robins, Emeritus Professor Bill CleggORCiD, Professor Todd Marder


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The compounds 4-ROC6F4C=CPh ( 4) where R = Me ( a), Et ( b), Pr-n ( c), Pr-i ( d), Bu-n ( e), n-C5H11 (f), PhCH2 (g), PhCH2CH2 (h), 4-MeC6H4 (i), 4-EtC6H4 (j) and menthyl (k), have been prepared by reaction of C6F5C=CPh (3) with ROH in the presence of KOH, and characterised by NMR (H-1, C-13, F-19) and mass spectroscopy. The single-crystal structures of PhC=CPh.C(6)F5C=CC6F5 (1: 2), 3 and 4a, c, d, f, g, i have been determined by X-ray diffraction at 120 - 160 K, and that of 3 also calculated by an ab initio pseudo-potential DFT method. The tolan moiety is nearly planar in each molecule except 4a, which has a Ph/C6F5 dihedral angle of 25.8degrees. The R group adopts an out-of-plane orientation except in 4f, where the n-pentyl chain is nearly coplanar with the C6F5 group at the cost of severe distortion of the C(ar) - C(ar)-O angles ( which differ by 13.5degrees). The structures of 1: 2, 3 (pseudo-isomorphous with 1: 2), 4a, 4g ( disordered) and 4i contain stacks of alternating arene and perfluoroarene moieties; 4c and 4d form discrete centrosymmetric dimers with arene/ perfluoroarene overlap, while 4f forms infinite stacks without such overlap. Differential thermal analysis and transmitted polarised light microscopy revealed no liquid-crystalline behaviour of 3 and 4.

Publication metadata

Author(s): Smith CE, Smith PS, Thomas RL, Robins EG, Collings JC, Dai CY, Scott AJ, Borwick S, Batsanov AS, Watt SW, Clark SJ, Viney C, Howard JAK, Clegg W, Marder TB

Publication type: Article

Publication status: Unknown

Journal: Journal of Materials Chemistry

Year: 2004

Volume: 14

Issue: 3

Pages: 413-420

ISSN (print): 0959-9428

ISSN (electronic): 1364-5501

Publisher: Royal Society of Chemistry


DOI: 10.1039/b314094f


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