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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 20, Number 3
BKCSDE 20(3)
March 20, 1999 

Synthesis and Cationic Polymerization of Multifunctional Vinyl Ethers Containing Dipolar Electronic Systems
Ju-Yeon Lee, Ji Hyang Kim, Min-Jung Kim
2,4-Di-(2'-vinyloxyethoxy)benzylidenemalononitrile (la), methyl 2,4-di-(2'-vinyloxyethoxy)benzylidenecyanoacetate (lb), 3,4-di-(2'-vinyloxyethoxy)benzylidene malononitrile (2a), methyl 3,4-di-(2'-vinyloxyethoxy)benzylidenecyanoacetate (2b), 2,5-di-(2'-vinyloxyethoxy)benzylidenemalononitrile (3a), methyl 2,5-di-(2'-vinyloxyethoxy)benzylidenecyanoacetate (3b), 2,3-di-(2'-vinyloxyethoxy)benzylidenemalononitrile (4a), and methyl 2,3-di-(2'-vinyloxyethoxy)benzylidenecyanoacetate (4b) were prepared by the condensation of 2,4-di-(2'-vinyloxyethoxy)benzaldehyde, 3,4-di-(2'-vinyloxyethoxy)benzaldehyde, 2,5-di-(2'-vinyloxyethoxy) benzaldehyde, and 2,3-di-(2'-vinyloxyethoxy)benzaldehyde with malononitrile or methyl cyanoacetate, respectively. Trifunctional divinyl ether monomers 1-4 were polymerized readily with boron trifluoride etherate as a cationic initiator to give optically transparent swelling poly(vinyl ethers) 5-8 havina oxybenzylidenemalononitrile and oxycyanocinnamate, which is presumably effective chromophore for second-order nonlinear optical applications. Polymers 5-8 were not soluble in common organic solvents such as acetone and DMSO due to crosslinking. Polymers 5-8 showed a thermal stability up to 300 ℃ in TGA thermograms, which is acceptable for electrooptic device applications.
307 - 313
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