title: Synthesis of photochromic oligophenylenimines: optical and computational studies.
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.
authors.affiliation: Ingeniería Mecánica Automotriz, Universidad Politécnica de Pachuca, Carretera Pachuca-Ciudad Sahagún km 20, Ex-Hacienda de Santa Bárbara, 43830 Zempoala, Hgo., Mexico.
authors.forename: Armando I Martínez
authors.initials: AI
authors.lastname: Pérez
authors.affiliation: Depto. Ing. Civil, Universidad de Guanajuato, Juárez 77, C.P. 36000 Leon, GTO, Mexico.
authors.forename: Oscar Coreño
authors.initials: OC
authors.lastname: Alonso
authors.affiliation: 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.
authors.forename: Julián Cruz
authors.initials: JC
authors.lastname: Borbolla
authors.affiliation: 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.
authors.forename: José M
authors.initials: JM
authors.lastname: Vásquez-Pérez
authors.affiliation: 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.
authors.forename: Juan Coreño
authors.initials: JC
authors.lastname: Alonso
authors.affiliation: 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.
authors.forename: Karina Alemán
authors.initials: KA
authors.lastname: Ayala
authors.affiliation: Centro de Investigación y de Estudios Avanzados del I. P. N., Libramiento Norponiente 2000, Fracc. Real de Juriquilla, C.P. 76230 Querétaro, Qro., Mexico.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Luna-Bárcenas
authors.affiliation: Facultad de Química, UNAM, Cd. Universitaria, Circuito exterior, Coyoacán, C.P. 04510 México, D.F., Mexico.
authors.forename: Thangarasu
authors.initials: T
authors.lastname: Pandiyan
authors.affiliation: 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. rosaangelesv@hotmail.com.
authors.forename: Rosa A Vázquez
authors.initials: RA
authors.lastname: García
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D055668:Photochemical Processes; D066244:Proton Magnetic Resonance Spectroscopy; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman
chemical_list: D000814:Aniline Compounds
references.citation: J Phys Chem A. 2007 Jul 5;111(26):5678-84
references.pmid: 17567110
references.citation: J Phys Chem A. 2012 Dec 6;116(48):11870-9
references.pmid: 23134517