Postfunctionalization of poly(propargyl methacrylate) using copper catalyzed 1,3‐dipolar Huisgen cycloaddition: An easy route to electro‐optic materials |
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| Authors: | Annabelle Scarpaci Clement Cabanetos Errol Blart Véronique Montembault Laurent Fontaine Vincent Rodriguez Fabrice Odobel |
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| Affiliation: | 1. Université de Nantes, CNRS, Chimie Et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France;2. LCOM‐Chimie des Polymères, UCO2M, UMR CNRS 6011, Université du Maine, Avenue O. Messiaen, 72085 Le Mans Cedex 9, France;3. Institut des Sciences Moléculaires, UMR5255 CNRS, 351 cours de la Libération, Université de Bordeaux, 33405 Talence Cedex, France |
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| Abstract: | A one‐pot synthetic route based on copper‐catalyzed Huisgen reaction has been developed to functionalize a methacrylate propargylic polymer with azido‐substituted moieties. This procedure was used for the preparation of electro‐optic materials containing well‐known Disperse Red One (DR1) chromophores along with bulky adamantyl moieties (Adam). The postfunctionalization of the propargylic polymer was successfully achieved using different molar ratios of DR1/Adam. These novel polymers exhibit high glass transition temperature owing to the rigid structure of adamantyl units. Moreover, the second harmonic generation measurements demonstrated the effectiveness of adamantyl groups to act as insulating shield limiting thus the electrostatic interactions between chromophores. Indeed, higher optimal chromophore concentration (50 mol %) than in conventional DR1‐containing polymers (30 mol %) allowed us to increase the d33 coefficient up to 92 pm/V. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 5652–5660, 2009 |
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| Keywords: | functionalization of polymers high temperature materials NLO structure‐property relations |
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