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Spectroscopic characterization of halogen- and cyano-substituted pyridinevinylenes synthesized without catalyst or solvent

M. Judith Percino, Víctor M. Chapela, Ling-Fa Montiel, Enrique Pérez-Gutiérrez, and José Luis Maldonado

Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, Complejo de Ciencias, ICUAP, Edif. 194, 22 Sur y San Claudio, C.P. 72570, Puebla, Puebla, México

 

E-mail: jpercino@siu.buap.mx

Received: 23 June 2009  Revised: 9 October 2009  Accepted: 20 October 2009

Abstract: An efficient Knoevenagel route using green chemistry conditions was applied for the synthesis of halogen- and cyano- substituted pyridinevinylene compounds. Absorption and fluorescence emission spectra of these conjugated compounds were recorded and compared in order to evaluate the effect of substituents on the electronic properties of pyridinevinylene compounds. The substituents studied were terminal Cl and F, two or three aromatic rings, as well as a cyano group attached to a C=C double bond. The compounds synthesized are: (E)-2-(4-fluorostyryl)pyridine, (E)-2-(4-chlorostyryl)pyridine, (E)-4-(4-chlorostyryl)pyridine, 2,3-diphenylacrylonitrile, 3-phenyl-2-(pyridin-2-yl)acrylonitrile, 3-phenyl-2-(pyridin-3-yl)acrylonitrile, 2-phenyl-3-(pyridin-2-yl)acrylonitrile, 3,3′-(1,4-phenylene)bis(2-phenylacrylonitrile), 3,3′-(1,4-phenylene)bis(2-(pyridin-2-yl)acrylonitrile), and 3,3′-(1,4-phenylene)bis(2-(pyridin-3-yl)acrylonitrile). The solvent-free method used in this work allows obtaining each compound by controlling the reaction temperature. The compounds were characterized by infrared spectroscopy and 1H-NMR spectroscopy.

Keywords: pyridinevinylenes - solvent free synthesis - Knoevenagel condensation

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-010-0012-z

 

Chemical Papers 64 (3) 360–367 (2010)

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