Synthesis of new photoresponsive polyesters containing norbornadiene residues by the polyaddition of donor-acceptor norbornadiene dicarboxylic acid diglycidyl ester with dicarboxylic acids and their photochemical properties

Citation
Y. Konno et al., Synthesis of new photoresponsive polyesters containing norbornadiene residues by the polyaddition of donor-acceptor norbornadiene dicarboxylic acid diglycidyl ester with dicarboxylic acids and their photochemical properties, J POL SC PC, 39(16), 2001, pp. 2683-2690
Citations number
14
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
ISSN journal
0887-624X → ACNP
Volume
39
Issue
16
Year of publication
2001
Pages
2683 - 2690
Database
ISI
SICI code
0887-624X(20010815)39:16<2683:SONPPC>2.0.ZU;2-9
Abstract
A donor-acceptor norbornadiene derivative, 5-(4-methoxyphenyl)-1,4,6,7,7-pe ntamethyl-2,5-norbornadiene-2,3-dicarboxylic acid diglycidyl ester (D-A NDG E), was synthesized by the reaction of the cesium salt of 5-(4-methoxypheny l)-1,4,6,7,7-pentamethyl-2,5-norbomadiene-2,3-dicarboxylic acid with epibro mohydrin in N-methyl-pyrrolidone (NMP). The polyaddition reactions of D-A N DGE with certain dicarboxylic acids were carried out with tetrabutylammoniu m bromide as a catalyst in NMP, producing corresponding polyesters containi ng D-A norbornadiene (NBD) residues in the main chain in fair to good yield s. The photoisomerization of the D-A NBD residues in the polyesters proceed ed very smoothly, forming the corresponding quadricyclane groups. The photo reactivities of the D-A NBD residues in the polymer were 50 times higher th an those of the NBD residues in the film state and 60 times higher than tho se in a tetrahydrofuran solution. The stored energy in the quadricyclane gr oups of the polymers was about 45-55 kJ/mol according to differential scann ing calorimetry analysis of the irradiated polymer films. (C) 2001 John Wil ey & Sons, Inc.