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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, Helena J., Thomas, Lynne H., Jones, Charlotte L., Teat, Simon J., Raithby, Paul R. and Wilson, Chick C. 2018. Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution. CrystEngComm 20 (22) 10.1039/C8CE00443A

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1466-8033
Date of First Compliant Deposit: 19 March 2020
Date of Acceptance: 7 May 2018
Last Modified: 24 Mar 2020 11:30
URI: http://orca.cardiff.ac.uk/id/eprint/130507

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