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Issue 27, 2017
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Modulating the assembly of N-benzylideneaniline by halogen bonding: crystal, cocrystal and liquid crystals

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Abstract

A novel halogen bonding (XB) donor–acceptor N-benzylideneaniline 3, containing one terminal of iodo-tetrafluorobenzene and the other side of 4-dimethylaminophenyl connected by a C[double bond, length as m-dash]N bond, has been designed and synthesized. As a self-assembled halogen-bonded motif, 3 exists in two conformations and they are antiparallel to generate fishbone-like stacks by π⋯π and C–I⋯π intermolecular interactions. As a halogen-bonded donor, it can connect with 4,4′-bipyridine to constitute 2 : 1 ratio cocrystal with C–I⋯NPy interactions. When the acceptor changes to 4-alkoxystilbazole, liquid crystal property varies with the length of the terminal chains. DSC and POM experiments demonstrated a series of XB liquid crystals. Among them, 3-A10 shows a long range of nematic phase and an integrated schlieren texture.

Graphical abstract: Modulating the assembly of N-benzylideneaniline by halogen bonding: crystal, cocrystal and liquid crystals

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Publication details

The article was received on 27 Apr 2017, accepted on 14 Jun 2017 and first published on 29 Jun 2017


Article type: Paper
DOI: 10.1039/C7CE00805H
CrystEngComm, 2017,19, 3801-3807

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    Modulating the assembly of N-benzylideneaniline by halogen bonding: crystal, cocrystal and liquid crystals

    Y. Wang, H. Shang, B. Li, H. Zhang and S. Jiang, CrystEngComm, 2017, 19, 3801
    DOI: 10.1039/C7CE00805H

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