Refractive Index Changes in Polymers Bearing Pendant Active Ester Groups by Thermal Rearrangement Reaction

Linear and branched polymers bearing S-(2-benzoxazolyl) thioester groups were selectively synthesized by free radical and photoinitiated radical polymerization, respectively, of S-(2-benzoxazolyl)-4-vinylthiobenzoate. Upon heating, the pendant S-(2-benzoxazolyl) thioester groups were converted to 3-...

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Veröffentlicht in:Chemistry letters 2011-12, Vol.40 (12), p.1363-1365
Hauptverfasser: Miyasaka, Makoto, Higurashi, Ayano, Kameyama, Atsushi
Format: Artikel
Sprache:eng
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Zusammenfassung:Linear and branched polymers bearing S-(2-benzoxazolyl) thioester groups were selectively synthesized by free radical and photoinitiated radical polymerization, respectively, of S-(2-benzoxazolyl)-4-vinylthiobenzoate. Upon heating, the pendant S-(2-benzoxazolyl) thioester groups were converted to 3-acylbenzoxazoline-2-thione groups, accompanied with a change of refractive index (Δn) of about +0.01 in both cases. The structural conversion was confirmed by UV–vis and IR spectroscopy, as well as comparison with authentic polymers bearing 3-acylbenzoxazoline-2-thione groups (similarly synthesized from 3-(4-vinylbenzoyl)benzoxazoline-2-thione). Application of such thermally induced rearrangement reactions may provide a new approach for obtaining materials whose refractive index can be changed by heat (e.g., generated by a laser beam).
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2011.1363