Salting Benzenes

Richard W. Gurney, Christine A. Mitchell, Sihyun Ham, Loyd D. Bastin, Bart Kahr

Research output: Contribution to journalArticle

Abstract

Simple salt crystals, such as potassium sulfate or barium acetate, were grown in the presence of a variety of aromatic molecules, especially aniline derivatives, bearing sulfonate or carboxylate substituents. We call this process salting, borrowing the term from Michl and co-workers who coined it in a related context (Kirkor, E.; Gebicki, J.; Phillips, D. R.; Michl, J. J. Am. Chem. Soc. 1986, 108, 7106-7107). Particular growth sectors of the resultant crystals were luminescent, and the emitted light was highly polarized indicating that the benzene derivatives were oriented inside of the salt lattices. These results are presented in the context of a generalization of single crystal matrix isolation; isomorphous matching of hosts and guests need not be a constraint. We show by polarization spectroscopy and magnetic resonance that different faces of the crystals will entrap molecules in different conformations otherwise separated by small energies in solution. Metastable triplet states are remarkably long-lived at room temperature in salt matrixes. The mechanisms of benzene derivative incorporation depend highly on secondary surface structures that are imaged by differential interference contrast microscopy. Luminescent molecules identify these features by lighting-up particular substructures and as such serve as probes of crystal growth mechanisms. We show how patterns of light in crystals are used to assign absolute growth directions. We conclude by arguing that the results herein can be extended to a limitless range of guests, while encouraging the use of salts as matrixes for the study of organic compounds.

Original languageEnglish (US)
Pages (from-to)878-892
Number of pages15
JournalJournal of Physical Chemistry B
Volume104
Issue number5
StatePublished - Feb 10 2000

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Benzene
Salts
Benzene Derivatives
benzene
salts
Crystals
Derivatives
Molecules
crystals
Bearings (structural)
matrices
molecules
Magnetic resonance
Barium
Aniline
Crystallization
sulfonates
aniline
substructures
organic compounds

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Gurney, R. W., Mitchell, C. A., Ham, S., Bastin, L. D., & Kahr, B. (2000). Salting Benzenes. Journal of Physical Chemistry B, 104(5), 878-892.

Salting Benzenes. / Gurney, Richard W.; Mitchell, Christine A.; Ham, Sihyun; Bastin, Loyd D.; Kahr, Bart.

In: Journal of Physical Chemistry B, Vol. 104, No. 5, 10.02.2000, p. 878-892.

Research output: Contribution to journalArticle

Gurney, RW, Mitchell, CA, Ham, S, Bastin, LD & Kahr, B 2000, 'Salting Benzenes', Journal of Physical Chemistry B, vol. 104, no. 5, pp. 878-892.
Gurney RW, Mitchell CA, Ham S, Bastin LD, Kahr B. Salting Benzenes. Journal of Physical Chemistry B. 2000 Feb 10;104(5):878-892.
Gurney, Richard W. ; Mitchell, Christine A. ; Ham, Sihyun ; Bastin, Loyd D. ; Kahr, Bart. / Salting Benzenes. In: Journal of Physical Chemistry B. 2000 ; Vol. 104, No. 5. pp. 878-892.
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