Abstract
The effect of acid-base interactions on the photophysical properties of 6,7-dimethoxy-3,4-dihydroisoquinoline in protic solvents is studied by the methods of steady-state and picosecond spectroscopy. It is found that the specific features of the spectral and luminescent properties of solutions of 6,7-dimethoxy-3,4-dihydroisoquinoline are connected with the presence of emission centers of two types—solvated initial molecules and their protonated cationic forms. Considerable long-wavelength shifts observed in the electronic absorption and fluorescence spectra of the cationic form of the molecule as compared to the spectra of its initial form are caused by the elongation of a conjugated chain present in the fragment of the molecule that separates the nitrogen atom and the oxygen atoms of the methoxy groups. The transition of the cationic form of the molecule to an excited electronic state is not accompanied by a change in its dipole moment.
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References
K. W. Bentley, Nat. Prod. Rep. 18, 148 (2001).
K. W. Bentley, Nat. Prod. Rep. 16, 367 (1999).
K. W. Bentley, Nat. Prod. Rep. 15, 341 (1998).
K. W. Bentley, Nat. Prod. Rep. 17, 247 (2000).
J. D. Scott and R. M. Williams, Chem. Rev. 102(5), 1669 (2002).
A. A. Akhrem, B. B. Kuz’mitskiĭ, F. A. Lakhvich, et al., in Chemistry and Biology of Immunoregulators (Zinatne, Riga, 1985) [in Russian].
D. Barton and W. D. Ollis, Comprehensive Organic Chemistry, Vol. 4: Heterocyclic Compounds, Ed. by P. G. Sammes (Pergamon, New York, 1979; Khimiya, Moscow, 1985).
The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13 ed. (Wiley, New York, 2001).
R. Yamaguchi, M. Tanaka, T. Matsuda, and A. Fujita, Chem. Commun. 21, 2213 (1999).
O. V. Gulyakevich, I. L. Rubinova, A. A. Govorova, et al., Mendeleev Commun. 4, 155 (2001).
O. V. Gulyakevich, P. V. Kurman, A. L. Mikhal’chuk, and A. A. Akhrem, Izv. Ross. Akad. Nauk, Ser. Khim., No. 2, 378 (2004).
O. V. Gulyakevich and A. L. Mikhal’chuk, Dokl. Akad. Nauk 390(4), 488 (2003) [Dokl. Chem. 390 (4), 141 (2003)].
R. B. Herbert, Nat. Prod. Rep. 18, 50 (2001).
E. McDonald, R. Ramage, R. N. Woodhouse, et al., J. Chem. Soc., Perkin Trans. 18, 2979 (1998).
R. B. Herbert, H. Venter, and S. Pos, Nat. Prod. Rep. 17, 317 (2000).
E. M. Olefirowicz and E. L. Elied, J. Org. Chem. 62(26), 9154 (1997).
T. Martinek, E. Forró, G. Günther, et al., J. Org. Chem. 65(2), 316 (2000).
D. Barbier, C. Marazano, and C. Riche, J. Org. Chem. 63(6), 1767 (1998).
L. Carrillo, D. Badia, E. Dominguez, et al., J. Org. Chem. 64(4), 1115 (1999).
T. R. Kelly, Y. Fu, and R. L. Xie, Tetrahedron Lett. 40(10), 1857 (1999).
V. L. Ponzo and T. S. Kaufman, J. Chem. Soc., Perkin Trans. 21, 3131 (1997).
O. V. Gulyakevich and A. L. Mikhal’chuk, Mendeleev Commun. 2, 72 (1997).
A. L. Mikhal’chuk, O. V. Gulyakevich, and A. A. Akhrem, BY Patent No. 5515, Ofits. Byll. Belgospatenta No. 3/1 (38), 153 (2003).
A. A. Akhrem, N. A. Borisevich, O. V. Gulyakevich, et al., Zh. Prikl. Spektrosk. 66(3), 440 (1999).
A. A. Akhrem, N. A. Borisevich, O. V. Gulyakevich, et al., J. Fluoresc. 9(4), 357 (1999).
N. A. Borisevich, V. L. Dubouski, L. A. Mikhal’chuk, et al., Zh. Prikl. Spektrosk. 70(4), 485 (2003).
N. A. Borisevich, V. L. Dubouski, A. L. Mikhalchuk, et al., Biopolimer 74(1–2), 105 (2004).
N. A. Borisevich, T. F. Raĭchenok, and V. D. Dubouski, Dokl. NAN Belarusi 48(2), 59 (2004).
N. A. Borisevich, T. F. Raĭchenok, A. A. Sukhodola, et al., Zh. Prikl. Spektrosk. 72(1), 48 (2005).
N. A. Borisevich, T. F. Raĭchenok, A. A. Sukhodola, and G. B. Tolstorozhev, Zh. Prikl. Spektrosk. 72(2), 192 (2005).
Excited States of Biological Molecules, Ed. by J. B. Birks (Wiley, New York, 1976), p. 652.
W. M. Whaley and T. R. Govindachari, Organic Reactions (Wiley, New York, 1951).
J. T. Sharp, J. Gosney, and A. G. Rowley, Practical Organic Chemistry, A Student Handbook of Techniques (Chapman and Hall, New York, 1999; Mir, Moscow, 1993).
G. B. Tolstorozhev and S. A. Tikhomirov, Zh. Prikl. Spektrosk. 65(5), 635 (1998).
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Original Russian Text © V.L. Dubouski, O.V. Gulyakevich, A.L. Mikhal’chuk, T.F. Raĭchenok, S.A. Tikhomirov, G.B. Tolstorozhev, 2006, published in Optika i Spektroskopiya, 2006, Vol. 100, No. 6, pp. 921–926.
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Dubouski, V.L., Gulyakevich, O.V., Mikhal’chuk, A.L. et al. Photophysical properties of solutions of 6,7-dimethoxy-3,4-dihydroisoquinoline. Opt. Spectrosc. 100, 848–853 (2006). https://doi.org/10.1134/S0030400X06060075
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DOI: https://doi.org/10.1134/S0030400X06060075