Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution
- Diamond Light Source, Didcot (United Kingdom)
- Univ. of Bath, Bath (United Kingdom)
- Univ. of Bath, Bath (United Kingdom); Univ. of Kent, Canterbury (United Kingdom)
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Univ. of Bath, Bath (United Kingdom); Harwell Science and Innovation Campus, Didcot (United Kingdom)
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.Varying the electronic character of the acid co-former substituent group predictably alters weak and strong intermolecular interactions.
- Research Organization:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Organization:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE
- Grant/Contract Number:
- AC02-05CH11231
- OSTI ID:
- 1437501
- Alternate ID(s):
- OSTI ID: 1465424
- Journal Information:
- CrystEngComm, Vol. 20, Issue 22; Related Information: © 2018 The Royal Society of Chemistry.; ISSN 1466-8033
- Publisher:
- Royal Society of ChemistryCopyright Statement
- Country of Publication:
- United States
- Language:
- English
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