Summary
5-Nitro-2-(2′-vinyloxyethoxy)benzylidenemalononitrile (2a), methyl 5-nitro-2-(2′-vinyloxyethoxy)benzylidenecyanoacetate (2b), 3-nitro-4-(2′-vinyloxyethoxy)benzylidenemalononitrile (4a), and methyl 3-nitro-4-(2′-vinyloxyethoxy)benzylidenecyanoacetate (4b) were prepared by the condensation of 5-nitro-2-(2′-vinyloxyethoxy)benzaldehyde (1) and 3-nitro-4-(2′-vinyloxyethoxy)benzaldehyde (3) with malononitrile or methyl cyanoacetate, respectively. Vinyl ether monomers 2a-b and 4a-b were polymerized with boron trifluoride etherate as a cationic initiator to yield poly(vinyl ethers) 5-6 having nitrooxybenzylidenemalononitrile and nitrooxycyanocinnamate, which is effective chromophore for second-order nonlinear optical applications. Polymers 5-6 were soluble in common organic solvents such as acetone and DMSO. T g values of the resulting polymer were in the range of 70–81°C. Electrooptic coefficient (r33) of the poled polymer films were in the range of 19–27 pm/V, which was improved by introducing of nitro group. Polymers 5–6 showed a thermal stability up to 300°C in TGA thermograms, which is acceptable for NLO device applications.
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Received: 24 November 1998/Revised version: 19 January 1999/Accepted: 29 January 1999
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Lee, JY., Ahn, MR. Synthesis of poly(ethyl vinyl ethers) containing two dipolar electronic systems and their properties. Polymer Bulletin 42, 237–244 (1999). https://doi.org/10.1007/s002890050458
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DOI: https://doi.org/10.1007/s002890050458