Abstract
The biphenyl derivative having two benzoylphenoxy groups at 2,2′-positions (1), is proved to be an efficient acyl-acceptant monomer for AlCl3-mediated Friedel–Crafts acylation polymerization. Diaroylation of biphenyl 1 with 4-chlorobenzoyl chloride (2a) in the presence of AlCl3 readily proceeds with continuous reactivity and high regioselectivity at 5,5′-positions to give the diaroylated biphenyl (3a) in good yields. Further, polymerization of monomer 1 with several arenedicarbonyl chlorides (4a–c) affords the corresponding wholly aromatic polyketones (6) with high molecular weights. These wholly aromatic polyketones are soluble in various organic solvents such as chloroform, THF, and so on. The superior heat resistibility of the resulting polyketones (6) is probably attributed to their characteristic polymer structures, i.e., all of the carbons involved in the polymer molecules have sp2 hybrid orbitals.
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Maeyama, K., Tagata, Y. & Yonezawa, N. 2,2′-Bis(4-benzoylphenoxy)biphenyl: A Novel Efficient Acyl-acceptant Monomer Yielding Wholly Aromatic Polyketones via Friedel–Crafts Type Polymerization with Arenedicarbonyl Chloride. Polym J 36, 146–150 (2004). https://doi.org/10.1295/polymj.36.146
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DOI: https://doi.org/10.1295/polymj.36.146
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