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Molecules 2015, 20(4), 5440-5455;

Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies

Ingeniería Mecánica Automotriz, Universidad Politécnica de Pachuca, Carretera Pachuca-Ciudad Sahagún km 20, Ex-Hacienda de Santa Bárbara, 43830 Zempoala, Hgo., Mexico
Depto. Ing. Civil, Universidad de Guanajuato, Juárez 77, C.P. 36000 Leon, GTO, Mexico
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
CONACyT, Avenida Insurgentes Sur 1582, Crédito Constructor, Benito Juárez, C.P. 03940 México, D.F., Mexico
Centro de Investigación y de Estudios Avanzados del I. P. N., Libramiento Norponiente 2000, Fracc. Real de Juriquilla, C.P. 76230 Querétaro, Qro., Mexico
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
Received: 1 January 2015 / Revised: 16 March 2015 / Accepted: 17 March 2015 / Published: 27 March 2015
(This article belongs to the Section Organic Chemistry)
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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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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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