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Issue 13, 2018
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Cooperative halogen bonding and polarized π-stacking in the formation of coloured charge-transfer co-crystals

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Abstract

Red co-crystals are formed between the matched complementary electron rich halogen bond acceptors, isomeric 4-(N,N-dimethylamino)phenylethynylpyridines and the electron poor halogen bond donor, 1-(3,5-dinitrophenylethynyl)-2,3,5,6-tetrafluoro-4-iodobenzene. The red 1 : 1 cocrystals exhibit strong halogen bonding and strong π-stacking. The N⋯I distances range from 2.80 to 2.85 Å and the C–I⋯N angles are between 169.9 and 175.8°. In all four structures the donor and acceptor molecules are alternately π-stacked with the centroid to centroid distances between the dinitrophenyl moiety and the dimethylaminophenyl moiety ranging from 3.61 to 3.73 Å. The calculated π–π stacking binding energy is −22.24 kcal mol−1 for the complex between 4-[4-(N,N-dimethylamino)phenylethynyl]pyridine and 1-(3,5-dinitrophenylethynyl)-2,3,5,6-tetrafluoro-4-iodobenzene while the calculated halogen bond binding energy between the same couple is −7.97 kcal mol−1.

Graphical abstract: Cooperative halogen bonding and polarized π-stacking in the formation of coloured charge-transfer co-crystals

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Publication details

The article was received on 08 Feb 2018, accepted on 27 Mar 2018 and first published on 10 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ00693H
Citation: New J. Chem., 2018,42, 10615-10622
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    Cooperative halogen bonding and polarized π-stacking in the formation of coloured charge-transfer co-crystals

    C. I. Nwachukwu, Z. R. Kehoe, N. P. Bowling, E. D. Speetzen and E. Bosch, New J. Chem., 2018, 42, 10615
    DOI: 10.1039/C8NJ00693H

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