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Molecules 2015, 20(4), 5440-5455; doi:10.3390/molecules20045440

Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies

1
Ingeniería Mecánica Automotriz, Universidad Politécnica de Pachuca, Carretera Pachuca-Ciudad Sahagún km 20, Ex-Hacienda de Santa Bárbara, 43830 Zempoala, Hgo., Mexico
2
Depto. Ing. Civil, Universidad de Guanajuato, Juárez 77, C.P. 36000 Leon, GTO, Mexico
3
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
4
CONACyT, Avenida Insurgentes Sur 1582, Crédito Constructor, Benito Juárez, C.P. 03940 México, D.F., Mexico
5
Centro de Investigación y de Estudios Avanzados del I. P. N., Libramiento Norponiente 2000, Fracc. Real de Juriquilla, C.P. 76230 Querétaro, Qro., Mexico
6
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 Synthesis)
View Full-Text   |   Download PDF [2102 KB, uploaded 31 March 2015]   |  

Abstract

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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MDPI and ACS Style

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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