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Open AccessArticle

Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies

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Ingeniería Mecánica Automotriz, Universidad Politécnica de Pachuca, Carretera Pachuca-Ciudad Sahagún km 20, Ex-Hacienda de Santa Bárbara, 43830 Zempoala, Hgo., Mexico
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Depto. Ing. Civil, Universidad de Guanajuato, Juárez 77, C.P. 36000 Leon, GTO, Mexico
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Académica de Ciencias de la Tierra y Materiales, Área Académica de Computación y Electrónica y Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Cd. Universitaria, C.P. 42184 Pachuca, Hgo., Mexico
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CONACyT, Avenida Insurgentes Sur 1582, Crédito Constructor, Benito Juárez, C.P. 03940 México, D.F., Mexico
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Centro de Investigación y de Estudios Avanzados del I. P. N., Libramiento Norponiente 2000, Fracc. Real de Juriquilla, C.P. 76230 Querétaro, Qro., Mexico
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Facultad de Química, UNAM, Cd. Universitaria, Circuito exterior, Coyoacán, C.P. 04510 México, D.F., Mexico
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2015, 20(4), 5440-5455; https://doi.org/10.3390/molecules20045440
Received: 1 January 2015 / Revised: 16 March 2015 / Accepted: 17 March 2015 / Published: 27 March 2015
(This article belongs to the Section Organic Chemistry)
Phenyleneimine oligomers 4,4'-(((1E,1'E)-(((1E,1'E)-(1,4-phenylenebis-(azanylylidene))bis(methanylylidene))bis(2,5-bis(octyloxy)-4,1-phenylene))bis(methanylyl-idene))-bis(azanylylidene))dianiline (OIC1MS) and 7,7'-(((1E,1'E)-(((1E,1'E)-((9H-fluorene-2,7-diyl)bis(azanylylidene))bis(methanylylidene))bis(2,5-bis(octyloxy)-4,1phenylene))bis- (methanylylidene))bis(azanylylidene))bis(9H-fluoren-2-amine) (OIC2MS) were prepared by means of conventional and mechanochemical synthesis and characterized by FT-IR, 1H- and 13C-NMR techniques. The optical properties of the compounds were studied in solution by using UV-visible spectroscopy, and the optical effects were analyzed as a function of solvent. The results show that OIC2MS exhibits interesting photochromic properties. Furthermore, the structural and electronic properties of the compounds were analyzed by TD-DFT. It was found that the mechanosynthesis is an efficient method for the synthesis of both tetraimines. View Full-Text
Keywords: mechanochemistry; oligoimines; conjugated; photochromism; DFT mechanochemistry; oligoimines; conjugated; photochromism; DFT
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Pérez, A.I.M.; Alonso, O.C.; Borbolla, J.C.; Vásquez-Pérez, J.M.; Alonso, J.C.; Ayala, K.A.; Luna-Bárcenas, G.; Pandiyan, T.; García, R.A.V. Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies. Molecules 2015, 20, 5440-5455.

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