Polycyclic Aromatic Hydrocarbon Solute Probes. Part 7: Evaluation of Additional Coronene Derivatives as Possible Solvent Polarity Probe Molecules Page: 479
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FIG. 4. Fluorescence emission spectra of naphtho[8,1,2abc]coronene
dissolved in [A (-)] dichloromethane; [B (- - -)] n-hexadecane; [C
(--)] acetonitrile; and [D ( ..... )] butyl acetate. In dichloromethane,
the three major emission bands occur at about 460, 480, and 490 nm.
coronene, and tetrabenzo[de,hi,mn,qr ]naphthacene.
Results of these measurements are explained in terms of
molecular symmetry and fluorescence emission fine
structure of the various PAH molecules.
The five coronene derivatives were prepared and pur-
ified by procedures described in the literature.17,18 Tet-
rabenzo[de,hi,mn,qr ]naphthacene was obtained by heat-
ing the twin [09,241[188.8.131.52]metacyclophane-9-ene with
palladium/charcoal and was purified by HPLC in accor-
dance with the method of Grutzmacher and Husemann.19
Stock solutions of each solute were prepared by dissolv-
ing the PAH in dichloromethane and were stored in the
o A C
0 1 L'-B
7 AA r A
-J; .Furseceeiso pcr f iabh[,,ac
o A C
chloromethane. In butyl acetate, the three major emission bands occur
PAH solutes and dichloromethane solvent. Carbon tet-
0 F o
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FIG. 6. Fluorescence emission spectra of naphth[2',1',8',7':
4,10,5]anthra[1,9,8abcd]coronene dissolved in [A (-)] butyl acetate;
[B (- - )] nhexadecane; [Crred into)] acetonitrile; and [D (- evap di-
chioromethane. in butyl acetate, the three major emission bands occur
at about 486, 510, and 519 nm.
dark to retard any photochemical reactions between the
PAH solutes and dichyoromethane solvent. Carbon tet-
rachloride and chloroform (to a much lesser extent) are
reported to react with polycyclic aromatic hydrocarbons
via a hypothesized concerted transannular addition with
free radical formation.20-24 Small aliquots of the stock
solution were transferred into test tubes, allowed to evap-
orate, and diluted with the organic solvent of interest.
Limited solubility of the larger PAH solutes did present
a problem in many of the solvents studied. The resulting
solutions had to be vigorously vortexed and warmed to
about 40-50C in order to redissolve the PAN molecule
back into solution from the test tube walls. Final solute
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FIG. 7. Fluorescence emission spectra of dinaphtho[8,1,2abc;
2',1',8'jkl]coronene dissolved in [A (-)] n-hexadecane; [B (- - -)]
dichloromethane; [C (... )] butyl acetate; and [D (- )] acetonitrile.
In butyl acetate, the four major emission bands occur at about 472,
481, 500, and 514 nm.
APPLIED SPECTROSCOPY 479
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Acree, William E. (William Eugene); Tucker, Sheryl A. (Sheryl Ann); Zvaigzne, Anita I.; Street, Kenneth W.; Fetzer, John Charles, 1953- & Grützmacher, Hans-Friedrich. Polycyclic Aromatic Hydrocarbon Solute Probes. Part 7: Evaluation of Additional Coronene Derivatives as Possible Solvent Polarity Probe Molecules, article, 1990; [Frederick, Maryland]. (digital.library.unt.edu/ark:/67531/metadc283656/m1/3/: accessed September 24, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.