Polycyclic Aromatic Nitrogen Heterocycles. Part III: Effect of Solvent Polarity and Solvent Acidity on the Fluorescence Emission Behavior of Select Azapyrenes and Phenanthroisoquinolines

Abstract

Fluorescence emission spectra are reported for 1-azapyrene, 2-azapyrene, 4-azapyrene, 12-azabenzo[a|pyrene, phenanthro[9,10g]isoquinoline, phenanthro[2,3h|isoquinoline, and phenanthro[3,2h]isoquinoline dissolved in organic nonelectrolyte solvents of varying polarity and acidity. Results of these measurements indicate that 12-azabenzo[a]pyrene, phenanthro[2,3h]isoquinoline, and phenanthro[3,2h]isoquinoline exhibit modest probe character as evidenced by decreased I/II or I/III band emission intensity ratios with increasing solvent polarity. Alcoholic solvents such as trifluoroethanol protonate the nitrogen hetero-atom, resulting in loss of emission fine structure accompanied by a sizeable red-shift in emission wavelength(s). For 1-azapyrene and 2-azapyrene the observed fluorescence emission spectra showed both neutral and protonated forms of the solute in trifluoroethanol.

Keywords

Fluorescence Molecular structure

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References

Stahlberg

and Almgren

, Anal. Chem. 57, 817 (1985).

Burrell

G. J.

and Hurtubise

R. J

, Anal. Chem. 60, 2178 (1988).

Burrell

G. J.

and Hurtubise

R. J

, Anal. Chem. 60, 564 (1988).

Waris

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).

Waris

Rembert

M. A.

Sellers

D. M.

Acree

W. E.

Jr. Street

K. W.

Jr. , and Fetzer

J. C.

, Analyst 114, 195 (1989).

Waris

Acree

W. E.

Jr. Street

K. W.

Jr. , and Fetzer

J. C.

, Appl. Spectrosc. 43, 845 (1989).

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).

Acree

W. E.

Jr. Tucker

S. A.

Cretella

L. E.

Zvaigzne

A. I.

Street

K. W.

Jr. Fetzer

J. C.

Nakasuji

and Murata

, Appl. Spectrosc. 44, 951 (1990).

Tucker

S. A.

Zvaigzne

A. I.

Acree

W. E.

Jr. Fetzer

J. C.

and Zander

, Appl. Spectrosc., 45, 424 (1991).

10.

Tucker

S. A.

Acree

W. E.

Jr. , and Tanga

M. J.

, Appl. Spectrosc. 45, 57 (1991).

11.

Bortolus

Galiazzo

and Gennari

, Anal. Chim. Acta 234, 353 (1990).

12.

Tanga

M. J.

and Reist

E. J

, J. Heterocyclic Chem. 23, 747 (1986).

13.

Cook

J. W.

and Thomson

W. H. S

, J. Chem. Soc. 395 (1945).

14.

Phillips

R. E.

Drub

G. H.

and Hunt

J. A

, J. Org. Chem. 37, 2030 (1972).

15.

Tanga

M. J.

Davis

R. F.

and Reist

E. J

, J. Heterocyclic Chem. 24, 39 (1987).

16.

Tanga

M. J.

and Reist

E. J

, J. Heterocyclic Chem. 28, 29 (1991).

17.

Dong

D. C.

and Winnik

M. A

, Can. J. Chem. 62, 2560 (1984).

18.

Nevstad

G. O.

and Songstad

, Acta Chem. Scand., Sect. B 38, 469 (1984).

19.

Selvarajan

Panicker

M. M.

Vaidyanathan

and Ramakrishnan

, Indian J. Chem. 18A, 23 (1979).

20.

Encinas

M. V.

Rubio

M. A.

and Lissi

, Photochem. Photobiol. 37, 125 (1983).

21.

Encinas

M. V.

Rubio

M. A.

and Lissi

E. A

, J. Photochem. 18, 137 (1982).

22.

Wiczk

W. M.

and Latowski

, Z. Naturforsch. 42A, 1290 (1987).

23.

Bowen

E. J.

and Rohatgi

K. K

, Disc. Faraday Soc. 14, 146 (1953).

24.

Carroll

F. A.

and Whitten

D. G

, J. Phys. Chem. 80, 2046 (1976).

25.

Tucker

S. A.

Cretella

L. E.

Waris

Street

K. W.

Jr. Acree

W. E.

Jr. , and Fetzer

J. C.

, Appl. Spectrosc. 44, 269 (1990).