Living ring-opening polymerization of ε-caprolactone catalyzed by β-quinolyl-enamino aluminium complexes: ligand electronic effects

Dalton Transactions : an International Journal of Inorganic Chemistry
Peng WangXia Chen

Abstract

A series of β-quinolyl-enamino aluminium complexes [AlLMe2] 1-7 {L = [(2-C9H6N)-CH[double bond, length as m-dash]C(4-MeC6H4)-N(Ar)-], Ar = C6H5(1), 4-FC6H4(2), 3,4,5-F3C6H2(3), C6F5(4), 5-tBuC6H4(5), 2,6-Me2C6H3(6), and 2,6-iPr2C6H3(7)} were synthesized by the reaction of AlMe3with the corresponding β-quinolyl-enamine ligands. All the complexes were characterized by1H and13C NMR spectroscopy and elemental analysis. The molecular structures of complexes 1-3 and 7 were confirmed by single-crystal X-ray diffraction, which revealed that all the Al atoms adopt a distorted tetrahedral geometry. These Al complexes were tested as the initiators for the ring-opening polymerization (ROP) of ε-caprolactone (ε-CL). The polymerization results showed that 1-5 in the presence of BnOH proceeded efficiently and their catalytic behaviors toward the ROP of ε-CL were significantly affected by the substituents of the aryl ring (Ar) on the end of the enamino framework, where the placement of electron-withdrawing substituents caused higher catalytic activity. However 6 and 7 displayed poor activity under the same conditions, suggesting that ortho-substituents on the Ar moieties hamper the coordination-insertion of the ε-CL monomer. The ROP of ε-CL by...Continue Reading

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Methods Mentioned

BETA
column chromatography
1
H
NMR
X-ray

Software Mentioned

SHELXL
2014

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