Spectroscopic Studies of the Interaction of 1,4-Diphenyl-1,3-Butadiene with α-,β-,and γ-Cyclodextrins

Abstract

Steady-state fluorescence, anisotropy, and UV-visible absorption measurements have been used to investigate the structure and spectroscopic characteristics of the complexes formed by trans, trans-1,4-diphenyl-1,3-butadiene (DPB) with α-, β-, and γ-cyclodextrins (CDs). The behavior of α-CD with DPB is very different from that of DPB with respect to β-CD or γ-CD. In the presence of α-CD, clear solutions with high absorption and fluorescence emission, relatively high anisotropy, a rapid equilibrium reaction, and Benesi–Hildebrand plots lead us to conclude that normal 2:1 inclusion compounds are formed. In the presence of γ-CD, turbid solutions, with absorption and fluorescence emission intensities lower than those in α-CD, higher values of anisotropy, slow equilibrium reaction, and spectral shifts to the red in the absorption, excitation, and emission wavelengths are evidence of the formation of extended linear aggregates. In the presence of β-CD, both mechanisms of inclusion appear to be present.

Keywords

Cyclodextrins UV-visible absorption Steady-state fluorescence Anisotrophy

Get full access to this article

View all access options for this article.

References

Szeijtli

, Cyclodextrins and their Inclusion Complexes (Akademiai Kiado, Budapest, 1982).

Szeijtli

, Cyclodextrin Technology (Kluwer, Dordrecht 1988).

Harada

and Kamachi

, Macromolecules 23, 2821 (1990).

Harada

and Kamachi

, J. Chem. Soc., Chem. Commun. 1322 (1990).

Harada

and Kamachi

, Nature 356, 325 (1992).

Harada

and Kamachi

, Nature 363, 516 (1993).

Wenz

and Keller

, Angew, Chem. Int. Ed. Engl, 31, 197 (1992).

Agbaria

R. A.

and Gill

, J. Phys. Chem. 92, 1052 (1988).

Agbaria

R. A.

and Gill

, J. Photochem. Photobiol. A: Chem. 78, 161 (1994).

10.

Agbaria

R. A.

Roberts

and Warner

I. M

, J. Phys. Chem. 99, 10056 (1995).

11.

and McGown

L. B

, Science 264, 249 (1994).

12.

Agnew

A. K.

McCarley

T. D.

Agbaria

R. A.

and Warner

I. M

, J. Photochem. Photobiol. A: Chem. 91, 205 (1995).

13.

Benesi-Hildebrand

H. A.

, J. Am. Chem. Soc. 71, 2703 (1949).

14.

Cantor

C. R.

and Schimmel

P. R

, Biophysical Chemistry, Part II: Techniques for the Study of Biological Structure and Function (W. H. Freeman and Company, San Francisco, 1980), Chap. 7, p.385.

15.

Lakowicz

J. R.

Cherek

and Mailiwal

B. P

, Biochemistry 24, 376 (1985).

16.

Yee

W. A.

Horwitz

J. S.

Goldbeck

R. A.

Einterz

C. M.

and Kliger

D. S

, J. Phys. Chem. 87, 380 (1983).

17.

Ramamurthy

Caspar

J. V.

Corbin

D. R.

Eaton

D. F.

Kauffman

J. S.

and Dybowski

, J. Photochem. Photobiol. A, Chem. 51, 259 (1990).