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Synthesis of ω‐functionalized poly(1,3‐cyclohexadiene): addition of fluorescent functional group to the polymer chain end
Author(s) -
Natori Itaru,
Sato Hisaya,
Natori Shizue
Publication year - 2008
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.2327
Subject(s) - polymer chemistry , polymer , alkyl , end group , polymerization , materials science , side chain , functional group , surface modification , fluorescence , chemical modification , living polymerization , anionic addition polymerization , chemistry , radical polymerization , organic chemistry , physics , quantum mechanics
BACKGROUND: Poly(1,3‐cyclohexadiene) (PCHD) is of interest as a precursor for the synthesis of a new class of high‐performance hydrocarbon polymers. ω‐Functionalization of PCHD offers a new opportunity for the preparation of a variety of multifunctional PCHD derivatives. RESULTS: ω‐Functionalized PCHD containing a fluorenyl (or anthracenyl) group at the polymer chain end was successfully synthesized by post‐polymerization reaction of poly(1,3‐cyclohexadienyl)lithium (PCHDLi) with alkyl halides containing a fluorescent functional group. The degree of nucleophilicity of PCHDLi and the control of side reactions were very important factors to achieve a high conversion for the post‐polymerization reactions of PCHDLi. The ω‐functionalized PCHDs obtained exhibited strong photoluminescence and the wavelength of the fluorescence was adjustable by changing the structure of the ω‐functional group. CONCLUSION: ω‐Functionalized PCHD is a preferable precursor that can be utilized to obtain a new class of multifunctional hydrocarbon polymers containing six‐membered rings in the main chain. Copyright © 2007 Society of Chemical Industry