Materials 2011, 4(3), 562-574; doi:10.3390/ma4030562
Article

Synthesis, Characterization and Photophysical Properties of Pyridine-Carbazole Acrylonitrile Derivatives

1 Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, Complejo de Ciencias, ICUAP, Edif. 103F, 22 Sur y San Claudio, C.P. Puebla 74570, Puebla, Mexico 2 Centro de Investigaciones en Óptica A.C. (CIO), Lomas del Bosque # 115, Col. Lomas del Campestre, C.P. 37150, León, Guanajuato, Mexico
* Author to whom correspondence should be addressed.
Received: 10 February 2011; in revised form: 24 February 2011 / Accepted: 9 March 2011 / Published: 11 March 2011
(This article belongs to the Special Issue Conjugated Polymers)
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Abstract: We synthesized three novel highly fluorescent compounds, 2-(2’-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile, 2-(3”-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile, and 2-(4-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile by Knoevenagel condensation. The first two were synthesized without solvent in the presence of piperidine as a catalyst; the third was synthesized without a catalyst and with N,N-dimethylformamide as a solvent. In solution, the molar absorption coefficients showed absorptions at 380, 378, and 396 nm, respectively; in solid state, absorptions were at 398, 390, and 442 nm, respectively. The fluorescence emission was at 540, 540 and 604 nm, respectively, the 2-(4-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile showed a red shift in the emission of 64 nm compared to the other two compounds. The fluorescence quantum yield for the compounds in powder form showed values of 0.05, 0.14, and 0.006, respectively; compared with the value measured for the Alq3 reference, 2-(3”-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile had a lightly higher value. The third harmonic generation measurement for 2-(2’-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile yielded a χ(3) value of 5.5 × 10−12 esu, similar to that reported for commercial polymers.
Keywords: conjugated compounds; ciano derivatives; optical properties; fluorescent compounds; powder fluorescent quantum yield

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MDPI and ACS Style

Pérez-Gutiérrez, E.; Percino, M.J.; Chapela, V.M.; Cerón, M.; Maldonado, J.L.; Ramos-Ortiz, G. Synthesis, Characterization and Photophysical Properties of Pyridine-Carbazole Acrylonitrile Derivatives. Materials 2011, 4, 562-574.

AMA Style

Pérez-Gutiérrez E, Percino MJ, Chapela VM, Cerón M, Maldonado JL, Ramos-Ortiz G. Synthesis, Characterization and Photophysical Properties of Pyridine-Carbazole Acrylonitrile Derivatives. Materials. 2011; 4(3):562-574.

Chicago/Turabian Style

Pérez-Gutiérrez, Enrique; Percino, M. Judith; Chapela, Víctor M.; Cerón, Margarita; Maldonado, José Luis; Ramos-Ortiz, Gabriel. 2011. "Synthesis, Characterization and Photophysical Properties of Pyridine-Carbazole Acrylonitrile Derivatives." Materials 4, no. 3: 562-574.

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