Synthesis of Photochromic Oligophenylenimines: Optical and Computational Studies

Author： Martínez Pérez Armando I. Coreño Alonso Oscar Cruz Borbolla Julián Vásquez-Pérez José M. Coreño Alonso Juan Alemán Ayala Karina Luna-Bárcenas Gabriel Pandiyan Thangarasu Vázquez García Rosa A.

Publisher： MDPI

E-ISSN： 1420-3049|20|4|5440-5455

ISSN： 1420-3049

Source： Molecules, Vol.20, Iss.4, 2015-03, pp. : 5440-5455

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Abstract

Phenyleneimine oligomers 4,4'-(((1E,1'E)-(((1E,1'E)-(1,4-phenylenebis-(azanylylidene))bis(methanylylidene))bis(2,5-bis(octyloxy)-1,4-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)-1,4-phenylene))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.