Chain Length Dependence of Hydrogen Bond Linkages between Cationic Constituents in Hydroxy-Functionalized Ionic Liquids: Tracking Bulk Behavior to the Molecular Level with Cold Cluster Ion Spectroscopy

Zeng, Helen J.; Menges, Fabian S.; Niemann, Thomas; Strate, Anne; Ludwig, Ralf; Johnson, Mark A.

doi:10.1021/acs.jpclett.9b03359

Chain Length Dependence of Hydrogen Bond Linkages between Cationic Constituents in Hydroxy-Functionalized Ionic Liquids: Tracking Bulk Behavior to the Molecular Level with Cold Cluster Ion Spectroscopy

Journal Article · Fri Jan 03 00:00:00 EST 2020 · Journal of Physical Chemistry Letters

DOI:https://doi.org/10.1021/acs.jpclett.9b03359· OSTI ID:1594083

^[1]; ^[2]; Niemann, Thomas ^[3]; Strate, Anne ^[3]; ^[4]; ^[2]

Yale Univ., New Haven, CT (United States). Sterling Chemistry Lab.; Sterling Chemistry Laboratory, Yale University, CT (United States)
Yale Univ., New Haven, CT (United States). Sterling Chemistry Lab.
Univ. of Rostock (Germany). Dept. of Chemistry and Dept. Life, Light & Matter
Univ. of Rostock (Germany). Dept. of Chemistry and Dept. Life, Light & Matter; Leibniz-Inst. für Katalyse, Rostock (Germany)

Hydroxy functionalization of cations in ionic liquids (ILs) can lead to formation of contacts between their OH groups [so-called (c–c) interactions]. One class of these linkages involves cooperatively enhanced hydrogen bonds to anionic partners that are sufficiently strong to overcome the repulsion between two positively charged centers. Herein, we clarify how the propensity for the formation of (c–c) contacts depends on the alkyl chain length between two cationic rings and their OH groups by analyzing the temperature-dependent IR spectra of bulk ILs as well as the vibrational predissociation spectra of ~35 K complexes comprised of two cations and one anion. This study compares the behavior of two cationic derivatives with ethyl and propyl chains complexed with two different anions: bis(trifluoromethylsulfonyl)imide and tetrafluoroborate. Only the bulk ILs with the longer chain propyl derivative [HPMPip+ = 1-(3-hydroxypropyl)-1-methylpiperidinium] display (c–c) interactions. Finally, molecular-level aspects of this docking arrangement are revealed by analyzing the OH stretching fundamentals displayed by the ternary complexes.

View Accepted Manuscript (DOE)

Research Organization:: Yale University, New Haven, CT (United States)

Sponsoring Organization:: Deutsche Forschungsgemeinschaft (DFG); US Air Force Office of Scientific Research (AFOSR); USDOE Office of Science (SC)

Grant/Contract Number:: FG02-06ER15800

OSTI ID:: 1594083

Journal Information:: Journal of Physical Chemistry Letters, Journal Name: Journal of Physical Chemistry Letters Journal Issue: 3 Vol. 11; ISSN 1948-7185

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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