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Issue 22, 2018
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Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution

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Abstract

Nine new molecular complexes of the proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) with substituted benzoic acid co-formers have been engineered with varying component stoichiometries (1 : 1, 1 : 2 or 1 : 3). These complexes are all ionic in nature, following proton transfer between the acid co-former and DMAN; the extracted proton is held by DMAN in all instances in an intramolecular [N–H⋯N]+ hydrogen bond. A number of structural features are common to all complexes and are found to be tunable in a predictable way using systematic acid co-former substitution. These features include charge-assisted hydrogen bonds formed between acid co-formers in hydrogen bonding motifs consistent with complex stoichiometry, and weak hydrogen bonds which facilitate the crystal packing of DMAN and acid co-former components into a regular motif. Possible crystal structure tuning by co-former substitution can aid the rational design of such materials, offering the potential to target solid-state properties that may be influenced by these interactions.

Graphical abstract: Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution

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Publication details

The article was received on 22 Mar 2018, accepted on 07 May 2018 and first published on 09 May 2018


Article type: Paper
DOI: 10.1039/C8CE00443A
Citation: CrystEngComm, 2018,20, 3074-3083
  • Open access: Creative Commons BY license
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    Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution

    L. K. Saunders, H. Nowell, H. C. E. Spencer, L. E. Hatcher, H. J. Shepherd, L. H. Thomas, C. L. Jones, S. J. Teat, P. R. Raithby and C. C. Wilson, CrystEngComm, 2018, 20, 3074
    DOI: 10.1039/C8CE00443A

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