3-(4-Bromophenyl)-5-(4-hydroxyphenyl)isoxazole: a versatile, new molecular building block for side-chain liquid crystal oligomers and polymers

Vilela, Guilherme D.; Fernandes, Thaís H. M.; da Rosa, Rafaela Raupp; Kelly, Stephen M.; Kitney, Stuart P.; Merlo, Aloir A.

Abstract

The synthesis and liquid crystalline behaviour of new comb-shaped methacrylate oligomers, derived from a new key intermediate in the synthesis of heterocyclic liquid crystals, i.e., 3-(4-bromophenyl)-5-(4-hydroxyphenyl)isoxazole, are reported. These new thermotropic liquid crystals exhibit a smectic A mesophase (SmA) above a soft crystal phase (CrE). The new methacrylate oligomers were synthesized by free radical polymerization of the corresponding monomers. Additionally, one main-chain liquid crystal polymer (MCLCPs) was prepared using a Mizoroki–Heck polymerization. Graphical abstract: 3-(4-Bromophenyl)-5-(4-hydroxyphenyl)isoxazole (2) is a new key intermediate in the synthesis of polymer and non polymer ordered liquid crystal phase.

Citation

Vilela, G. D., Fernandes, T. H. M., da Rosa, R. R., Kelly, S. M., Kitney, S. P., & Merlo, A. A. (2016). 3-(4-Bromophenyl)-5-(4-hydroxyphenyl)isoxazole: a versatile, new molecular building block for side-chain liquid crystal oligomers and polymers. Polymer Bulletin, 73(4), 959-973. https://doi.org/10.1007/s00289-015-1529-7

• Journal Article Type: Article
• Acceptance Date: Sep 11, 2015
• Online Publication Date: Sep 29, 2015
• Publication Date: Apr 1, 2016
• Deposit Date: Sep 21, 2017
• Journal: Polymer Bulletin
• Electronic ISSN: 1436-2449
• Publisher: Springer Verlag
• Peer Reviewed: Peer Reviewed
• Volume: 73
• Issue: 4
• Pages: 959-973
• DOI: https://doi.org/10.1007/s00289-015-1529-7
• Keywords: Oligomers methacrylates, Isoxazoles, Isoxazolines, Liquid crystals
• Public URL: https://hull-repository.worktribe.com/output/454970
• Publisher URL: https://link.springer.com/article/10.1007%2Fs00289-015-1529-7
• Additional Information: This is a description of an article published in Polymer Bulletin, 2016, v.73 issue 4.