Abstract
The bulk polymerization behavior of l‐lactide monomer using dibenzoylmethane (DBM)‐based Sn(II) compounds (DBM)Sn(OBu) (2) and (DBM) 2Sn (3) is investigated. Compounds 2 and 3 were prepared from the reaction of Sn(OBu)2 (1) with 1 or 2 equiv of DBM, respectively. X‐ray diffraction studies revealed that, while 2 exists as a dimeric form linked by 1‐butoxide bridges, 3 is monomeric in the solid state. The Sn(II) centers in both compounds adopt distorted square‐pyramidal geometry. Ring‐opening polymerization of l‐lactide with 1–3 efficiently produced poly(l‐lactide)s with high molecular weight and narrow polydispersities (PDI < 2). The catalytic activity was found to be in the order 1 > 2 > 3, indicating that the DBM ligand causes a sluggish coordinative insertion of the lactide monomer into the Sn(II) center. In particular, the addition of dodecanol (DDO, 0.1 mol%) substantially improved the catalytic activity for all compounds. The comparative polymerization using Sn(Oct)2 (Oct = 2‐ethylhexanoate) in the absence and presence of DDO further showed that 1 is higher in activity than Sn(Oct)2 and that Sn(II) alkoxides are the actual active species in the polymerization of l‐lactide.
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