Synthèse et propriétés photochimiques de modèles imides et amides contenant des structures norbornadiènes pentaméthylés

Abstract

Me ´moire/Full paper Synthe `se et proprie ´te ´s photochimiques de mode `les imides et amides contenant des structures norbornadie `nes pentame ´thyle ´s Synthesis and photochemical properties of imide and amide models containing pentamethylated norbornadiene residues Ahmed Oueslati a , Hatem Ben Romdhane b, *, Re ´gis Mercier c , Refaa ˆt M. Chaa ˆbouni a a Unite´de recherche synthe`se et analyse de mate´riaux, de´partement de ge´nie industriel, E ´cole nationale d'inge´nieurs de Tunis, BP 37, 1002 Le Belve´de`re-Tunis, Tunisie b Laboratoire de chimie organique structurale, synthe`se et e´tudes physicochimiques, faculte´des sciences de Tunis, campus universitaire, 2092

Synthesis and photochemical properties of novel pentamethylated norbornadiene containing polyimides

“…For the kinetic study, the procedure used for the model compounds and elsewhere published29 was retained. Because the experiences were performed with very thin polymer films, it was assumed that the Beer Lambert's law was applicable.…”

“…In a previous work,29 we addressed the synthesis of four pentamethylated NBD models containing imide, bisimide, and diamides moieties and the study of the photochemical isomerization NBD to QC derivatives under solar light irradiations. The results show for all these models that more than 70% of NBD are transformed into QC after only 30 min, and the kinetic reaction is of a first‐order rate.…”

Photoresponsive polyamides containing pentamethylated norbornadiene moieties: Synthesis and photochemical properties under sunlight irradiation

“…All solvents were carefully dried and freshly distilled according to common laboratory techniques. 1‐Benzyl‐1,2,3,4,5‐pentamethylcyclopenta‐2,4‐diene and pentamethylated NBD dicarboxylic acid 1 were prepared as previously reported . 4,4′‐Oxydianiline ( 2 , Acros organics, 98%) was purified by vacuum sublimation.…”

“…The photoresponsive properties of NBD‐containing polymer materials are usually studied under monochromatic UV irradiation and to the best of our knowledge have never been carried out under sunlight irradiation. We have previously reported the photochemical behavior of NBD‐containing amide and imide models, as well as the photochemical properties of polyimides containing main‐chain pentamethylated NBD moieties obtained by step growth polymerization of a dianhydride pentamethylated NBD with different aromatic diamines . UV/vis spectroscopy of irradiated polymer films has shown that the photochemical isomerization of NBD groups into QC ones proceeds following a first‐order kinetic.…”

Photochemical isomerization of norbornadiene‐containing polytriazoles obtained by click chemistry polyaddition

“…Dicylopentadiene (95%), sodium hydride (60 wt % in paraffin oil), propargyl bromide (80% in toluene), 18‐crown‐6 (99%), potassium carbonate (99%), sodium azide (99.5%), N , N ‐diisopropylethylamine (DIPEA, 99%), 4,4′‐dihydroxybenzophenone (99%), iodo (triethylphosphite) copper(I) (97%), anhydrous tetrahydrofuran (THF, 99.9%), potassium hydroxide (85%), propargyl alcohol (99%), acetylene dicarboxylic acid (95%), but‐2‐yne‐1,4‐diol diacetate (95%), N , N′ ‐dicyclohexylcarbodiimide (99%), 4‐dimethylaminopyridine (DMAP, 99%), and 1,2‐dibromoethane (98%) were purchased from Aldrich and used as received. 2,5‐Norbornadiene‐2,3‐dicarboxylic acid 1 , 2,5‐norbornadiene‐2,3‐dimethylacetate 3 , 2,5‐norbornadiene‐2,3‐diol 4 , and aromatic diazides 6–9 , were prepared according to previously reported methods.…”