Dataset Information

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.

SUBMITTER: Perez AI

PROVIDER: S-EPMC6272491 | biostudies-other | 2015

REPOSITORIES: biostudies-other

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Synthesis of photochromic oligophenylenimines: optical and computational studies.

Pérez Armando I Martínez AI Alonso Oscar Coreño OC Borbolla Julián Cruz JC Vásquez-Pérez José M JM Alonso Juan Coreño JC Ayala Karina Alemán KA Luna-Bárcenas Gabriel G Pandiyan Thangarasu T García Rosa A Vázquez RA

Molecules (Basel, Switzerland) 20150327 4

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 ...[more]

PMID: 25826785

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Project description:The aim of our study was to quantitatively evaluate the optical properties of photochromic lenses available on the market under cold and warm temperatures corresponding to the winter and summer seasons. The transmittance of 12 photochromic lenses from five manufacturers was measured using an UV/VIS spectrophotometer at cold (6 ± 2°C) and at warm (21 ± 2°C) temperatures. Transmittances were recorded from 380 to 780 nm and at the wavelength with maximum absorbance, which was calculated from the transmittance. The characteristics of the lenses were evaluated by examining changes in the optical properties at colorless and colored states and in the fading rate depending on temperature. The wavelength with maximum absorbance for photochromic lenses at the cold temperature showed a shorter shift than that at the warm temperature. The photochromic properties at the cold temperature were 11.5% lower for transmittance, 1.4 times higher for the change in optical density, and 1.2 times higher for the change in transmittance in the colored and colorless states, optical blocking % ratio, and change in luminous transmittance as compared to those at the warm temperature in the colored state. The fading rates based on the half-life time at the cold temperature were from 2.7 to 5.4 times lower than those at the warm temperature. The fading time until 80% transmittance was 6.4 times longer at the cold as compared to that at the warm temperature. There were significant differences in the optical properties of the photochromic lenses in terms of an absorbance at a shorter wavelength, a lower transmittance, a higher optical density, optical blocking % ratio, and luminous transmittance at the cold as compared to the warm temperature. Hence, it is necessary to provide consumers with information on photochromic optical properties, including the transmittance in colored and colorless states, and the fading rates at temperatures corresponding to the summer and winter seasons for each product.

Dataset Information

Synthesis of photochromic oligophenylenimines: optical and computational studies.

Publications

Synthesis of photochromic oligophenylenimines: optical and computational studies.

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