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

Saunders, Lucy K., Nowell, Harriott, Spencer, Helen C. E., Hatcher, Lauren E., Shepherd, H.J., Thomas, Lynne H., Jones, Charlotte L., Teat, Simon J., Raithby, Paul R., Wilson, Chick C. and others. (2018) Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution. CrystEngComm, 20 (22). pp. 3074-3083. ISSN 1466-8033. (doi:10.1039/C8CE00443A) (KAR id:67343)

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https://doi.org/10.1039/C8CE00443A

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.

Item Type: Article
DOI/Identification number: 10.1039/C8CE00443A
Subjects: Q Science
Divisions: Divisions > Division of Natural Sciences > School of Physical Sciences
Depositing User: Helena Shepherd
Date Deposited: 15 Jun 2018 14:57 UTC
Last Modified: 16 Feb 2021 13:55 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/67343 (The current URI for this page, for reference purposes)
Shepherd, H.J.: https://orcid.org/0000-0003-0832-4475
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