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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. ORCID: https://orcid.org/0000-0002-1549-9727, 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: 07 Nov 2022 09:53
URI: https://orca.cardiff.ac.uk/id/eprint/130507

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