Abstract
Nitromethane is examined as a selective quenching agent for discriminating between “alternant” versus “nonalternant” polycyclic aromatic hydrocarbons in unknown mixtures. Of the 36 benzenoid solutes studied, only dibenzo[hi,wx]heptaphene failed to obey the selective quenching rule. Also reported are new experimental fluorescence probe studies for dibenzo[de,st]pentacene, dibenzo[fg,qr]pentacene, naphtho[8,1,2hij)-hexaphene, benzo[vwx]hexaphene, benzo[1,2,3cd;4,5,6c'd‘]diperylene, dibenzo[hi,wx]heptacene, benzo[b]triphenylene, chrysense, and anthracene dissolved in nonelectrolyte solvents of varying polarity. Benzo-[vwx]hexaphene was found to exhibit probe character, as evidenced by a systematic variation in emission intensity ratio with solvent polarity.
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References
1.
Waris
R.
Rembert
M. A.
Sellers
D. M.
Acree
W. E.
Jr.
Street
K. W.
Jr.
Poole
C. F.
Shetty
P. H.
and
Fetzer
J. C
, Appl. Spectrosc. 42 , 1525 (1988 ).
2.
Waris
R.
Rembert
M. A.
Sellers
D. M.
Acree
W. E.
Jr.
Street
K. W.
Jr.
, and
Fetzer
J. C.
, Analyst 114 , 195 (1989 ).
3.
Waris
R.
Acree
W. E.
Jr.
Street
K. W.
Jr.
, and
Fetzer
J. C.
, Appl. Spectrosc. 43 , 845 (1989 ).
4.
Acree
W. E.
Jr.
Tucker
S. A.
Zvaigzne
A. I.
Street
K. W.
Jr.
Fetzer
J. C.
and
Grutzmacher
H.-F
, Appl. Spectrosc. 44 , 477 (1990 ).
5.
Acree
W. E.
Jr.
Tucker
S. A.
Cretella
L. E.
Zvaigzne
A. I.
Street
K. W.
Jr.
Fetzer
J. C.
Nakasuji
K.
and
Murata
I
, Appl. Spectrosc. 44 , 951 (1990 ).
6.
Tucker
S. A.
Zvaigzne
A. I.
Acree
W. E.
Jr.
Fetzer
J. C.
and
Zander
M
, Appl. Spectrosc. 45 , 424 (1991 ).
7.
Tucker
S. A.
Teng
I.-L.
Acree
W. E.
Jr.
, and
Fetzer
J. C.
, Appl. Spectrosc. 45 , 186 (1991 ).
8.
Acree
W. E.
Jr.
Tucker
S. A.
and
Fetzer
J. C
, Polycyclic Aromat. Comnds. 2 . 75 (1991 ).
9.
Tucker
S. A.
Acree
W. E.
Jr.
, and
Tanga
M. J.
, Appl. Spectrosc. 45 , 57 (1991 ).
10.
Tucker
S. A.
Acree
W. E.
Jr.
, and
Tanga
M. J.
, Appl. Spectrosc. 45 , 911 (1991 ).
11.
Tucker
S. A.
Acree
W. E.
Jr.
Tanga
M. J.
Zander
M.
Fetzer
J. C.
Tokita
S.
Hiruta
K.
Kitahara
K.
and
Nishi
H
, Appl. Spectrosc. 45 , 1188 (1991 ).
12.
Tucker
S. A.
Acree
W. E.
Jr.
Cho
B. P.
Harvey
R. G.
and
Fetzer
J. C
, Appl. Spectrosc. 45 , 1699 (1991 ).
13.
Cecil
T. L.
and
Rutan
S. C
, Anal. Chem. 62 , 1998 (1990 ).
14.
Lakowicz
J. R.
, Principles of Fluorescence Spectroscopy (Plenum Press , New York , 1983 ).
15.
Kalman
R. E.
, J. Basic Eng. 82 , 34 (1964 ).
16.
Rutan
S. C.
, J. Chemom. 1 , 7 (1987 ).
17.
Brown
S. D.
, Anal. Chim. Acta 181 , 1 (1986 ).
18.
Rutan
S. C.
Gerow
D. D.
and
Hartmann
G
, Intell. Lab. Sys. 3 , 61 (1988 ).
19.
Gampp
H.
Maeder
M.
Meyer
C. J.
and
Zuberbühler
A. D
, Talanta 32 , 1133 (1985 ).
20.
Maeder
M.
, Anal. Chem. 59 , 527 (1987 ).
21.
Millican
D. W.
and
McGown
L. B
, Appl. Spectrosc. 46 , 28 (1992 ).
22.
Millican
D. W.
and
McGown
L. B
, Anal. Chem. 61 , 580 (1989 ).
23.
Millican
D. W.
and
McGown
L. B
, Anal. Chem. 62 , 2242 (1990 ).
24.
Blümer
G.-P.
and
Zander
M
, Fresenius Z. Anal. Chem. 296 , 409 (1979 ).
25.
Chen
S.-H.
Evans
C. E.
and
McGuffin
V. L
, Anal. Chim. Acta 246 , 65 (1991 ).
26.
Olea
A. F.
and
Thomas
J. K
, J. Am. Chem. Soc. 110 , 4494 (1988 ).
27.
Amszi
V. L.
Cordero
Y.
Smith
B.
Tucker
S. A.
Acree
W. E.
Jr.
Yang
C.
Abu-Shaqara
E.
and
Harvey
R. G
, Appl. Spectrosc. 46 , 1156 (1992 ).
28.
Konash
P. L.
Wise
S. A.
May
W. E.
and
Liq
J
, Chromatogr. 4 , 1339 (1981 ).
29.
Zimmerman
H. E.
, Quantum Mechanics for Organic Chemists (Academic Press , New York , 1975 ), pp. 145 –146 .
30.
March
J.
, Advanced Organic Chemistry: Reactions, Mechanisms and Structure (McGraw-Hill , New York , 1968 ), pp. 46 –48 .
31.
Clar
E.
Ironside
C. T.
and
Zander
M
, Tetrahedron 22 , 3527 (1966 ).
32.
Clar
E.
, Berichte 65 , 846 (1932 ).
33.
Clar
E.
, Polycyclic Aromatic Hydrocarbons (Academic Press , New York , 1964 ), Vol. 2 , p. 53 .
34.
Zander
M.
and
Franke
W
, Chem. Ber. 94 , 446 (1961 ).
35.
Clar
E.
and
Zander
M
, Tetrahedron 19 , 521 (1963 ).
36.
Clar
E.
Kelley
W.
and
Laird
R. M
, Monatshefte 87 , 391 (1956 ).
37.
Fetzer
J. C.
and
Biggs
W. R
, J. Chromatogr. 295 , 161 (1984 ).
38.
Fetzer
J. C.
and
Biggs
W. R
, J. Chromatogr. 322 , 275 (1985 ).
39.
Dong
D. C.
and
Winnick
M. A
, Can. J. Chem. 62 , 2560 (1984 ).
40.
De Jersey
J.
Jeffers-Morley
P.
and
Martin
R. B
, Biophys. Chem. 13 , 233 (1981 ).
41.
Meyerhoffer
S. M.
and
McGown
L. B
, Anal. Chem. 63 , 2082 (1991 ).
42.
Nakajima
A.
, J. Lumin. 8 , 266 (1974 ).
43.
Dias
J. R.
, Ace. Chem. Res. 18 , 241 (1985 ).
44.
Dias
J. R.
, Handbook of Polycyclic Aromatic Hydrocarbons , Part A (Elsevier , Amsterdam, The Netherlands , 1987 ).
45.
Dias
J. R.
, Handbook of Polycylic Aromatic Hydrocarbons , Part B (Elsevier , Amsterdam, The Netherlands , 1988 ).
46.
Herbstein
F. H.
and
Schmidt
G. M. J
, J. Chem. Soc. , 3302 (1954 ).
47.
Hirshfeld
A. L.
Sandler
S.
and
Schmidt
G. M. J
, J. Chem. Soc. , 2108 (1963 ).
48.
Hirshfeld
A. L.
, J. Chem. Soc. , 2126 (1963 ).
49.
McIntosh
A. O.
Robertson
J. M.
and
Vand
V
, J. Chem. Soc. , 1661 (1954 ).
50.
De Rango
C.
Tsoucaris
G.
Declerq
J. P.
Germain
G.
and
Petzeys
J. P
, Cryst. Struct. Comm. 2 , 189 (1973 ).
51.
Herbstein
F. H.
, Acta Crystallogr. B35 , 1661 (1979 ).
52.
Roberts
P. J.
and
Ferguson
G
, Acta Crystallogr. B33 , 1244 (1977 ).
53.
Laarhoven
W. H.
and
Prinsen
W. J. C
, Top. Curr. Chem. 125 , 63 (1984 ) and references therein.
54.
Meurer
K. P.
and
Vogtle
F
, Top. Curr. Chem. 127 , 1 (1985 ) and references therein.
55.
Herndon
W. C.
Nowak
P. C.
Conner
D. A.
and
Lin
P
, J. Am. Chem. Soc. 114 , 41 (1992 ).
56.
Dreeskamp
H.
Koch
E.
and
Zander
M
, Z. Naturforsch. 30A , 1311 (1975 ).
57.
Breymann
U.
Dreeskamp
H.
Koch
E.
and
Zander
M
, Fresenius Z. Anal. Chem. 293 , 208 (1978 ).
58.
Breymann
U.
Dreeskamp
H.
Koch
E.
and
Zander
M
, Chem. Phys. Lett. 59 , 68 (1978 ).