Push-Pull Tricyanovinyl-Substituted Thienylpyrroles: Synthesis, Solvatochromic and Electrochemical Properties

Article Preview

Abstract:

New tricyanovinyl- derivatives 1 of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 have been synthesized and characterized. Compounds 1 display dramatic reductions in both their optical and electrochemical band gaps in comparison to thienylpyrroles 2. The solvatochomic behavior of tricyanovinyl- derivatives 1 was investigated in a variety of solvents. In agreement with the solvatochromic and the electrochemical studies for push-pull derivatives 1 the new compounds prepared, can find application for manufacturing new materials with notable non-linear optical properties.

You might also be interested in these eBooks

Info:

Periodical:

Materials Science Forum (Volumes 514-516)

Pages:

98-102

Citation:

Online since:

May 2006

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2006 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

[1] D.S. Chemla and J. Zyss: Non linear Optical Properties of Organic Molecules and Crystals, Vols. 1 and 2 (Academic Press, Orlando 1987).

Google Scholar

[2] V.P. Rao, A.K. -I. Jen, K.I. Wong and K.J. Drost: Tetrahedron Lett. Vol. 34 (11) (1993), p.1747.

Google Scholar

[3] M.M.M. Raposo and G. Kirsch: Tetrahedron Vol. 59 (26) (2003), p.4891.

Google Scholar

[4] M.M.M. Raposo, A.M.C. Fonseca and G. Kirsch: Tetrahedron Vol. 60 (18) (2004), p.4071.

Google Scholar

[5] M.M.M. Raposo, A.M.C. Fonseca and G. Kirsch: Mater. Sci. Forum Vol. 455-456 (2004), p.157.

Google Scholar

[6] R.M.F. Batista, S.P.C. Costa and M.M.M. Raposo: Tetrahedron Lett. Vol. 45 (13) 2004, p.2825.

Google Scholar

[7] R. Zhao, M. Akazome, S. Matsumoto and K. Ogura: Tetrahedron Vol. 58 (51) (2002), p.10225.

Google Scholar

[8] K. Eckert, A. Schroder and H. Hartmann: Eur. J. Org. Chem. Vol. 7 (2000), p.1327 and references cited therein.

Google Scholar

[9] M.M.M. Raposo and G. Kirsch: Heterocycles Vol. 55 (8) (2001), p.1487.

Google Scholar

[10] F. Costa, C.J.R. Silva, M.M.M. Raposo, A.M. Fonseca, I.C. Neves, A.P. Carvalho and J. Pires: Microporous Mesoporous Mater. Vol. 72 (1-3) (2004), p.111.

DOI: 10.1016/j.micromeso.2004.04.003

Google Scholar

[11] M.M.M. Raposo, A.M.B. A Sampaio and G. Kirsch: Synthesis Vol. 2 (2005), p.199.

Google Scholar

[12] A. H. Jackson: The Chemistry of Heterocyclic Compounds; Vol. 48, Part 1, p.295, R. A. Jones editor, (Wiley, New York 1990) and references cited therein.

Google Scholar

[13] J. Casado, J.T.M. Pappenfus, L.L. Miller, K.R. Mann, E. Orti, P M. Viruela, R. Pou-Amerigo, V. Hernandez, and J. T L. Navarrete: J. Am. Chem. Soc. Vol. 125 (9) (2003), p.2524.

Google Scholar

[14] M.J. Kamlet, J. -L. M. Abboud, M.H. Abraham and R.W. Taft: J. Org. Chem. Vol. 48 (17) (1983), p.2877 and references cited therein.

Google Scholar

[15] M.J. Kamlet, J. -L. M. Abboud, M.H. Abraham and R.W. Taft: J. Am. Chem. Soc. Vol. 99 (18) (1977), p.6027.

Google Scholar

[16] F. Effenberger, F. Wuerthner, F. Steybe: J. Org. Chem. Vol. 60 (7) (1995), p. (2082).

Google Scholar

[17] T. McCormac and D. Farrell: Electrochimica Acta Vol. 46 (20-21) (2001), p.3287.

Google Scholar

[18] J. Pei, J. Ni, X. H. Zhou, X.L. Cao and Y.H. Lai: J. Org. Chem. Vol. 67 (23) (2002), p.8104.

Google Scholar