Chinese Journal of Organic Chemistry >
Silylene/Organoaluminum Lewis Pair System and the Initiation Property for Polymerization of (Meth)acrylates
Received date: 2023-05-15
Revised date: 2023-08-05
Online published: 2023-09-08
Supported by
National Natural Science Foundation of China(21972112)
The initiation polymerization property of (meth)acrylates by using the silylene/organoaluminum Lewis pair (LP) system is studied. Four silylenes L(Ph2P)Si (Si-1, L=PhC(NtBu)2), L[4-MeC6H4(Ph2P)N]Si (Si-2), L[2,6-iPr2C6H3(1,5- C8H14B)N]Si (Si-3), and L(LSi)Si (Si-4) as the Lewis base (LB) were synthesized, together with six organoaluminums Al(C6F5)3, AlMe(BHT)2, AliBu(BHT)2, AliBu2(BHT), AliBu(BHT*)2, and AliBu2(BHT*) (BHT=2,6-tBu2-4-MeC6H2O and BHT*=2,4,6-tBu3C6H2O) as the Lewis acid (LA). Si-1/organoaluminum and Si-4/organoaluminum LP systems all enable to initiate the complete methacrylate (MMA) polymerization, achieving turnover of frequency (TOF) activities in the range of 50~400 h-1 with PMMA Mn of 82000~271000 and Đ of 1.11~1.81. Neither Si-2/organoaluminum or Si-3/organoaluminum was active. The Si-1/Al(C6F5)3 displayed poor reactivity on n-butyl acrylate (nBA) and 2-ethylhexyl acrylate (EHA). However, the Si-1/other organoaluminums exhibited both complete nBA and EHA polymerizations. For nBA, the TOFs were obtained by 4.8×104~14.4×104 h-1, in which the PnBAs were produced with Mn 100000~179000 and Đ 1.08~1.59. For EHA, the TOFs were up to 14.4×104~36.0×104 h-1, where the PEHAs were yielded with Mn 81000~240000 and Đ 1.12~1.95. The probable polymerization mechanism with the silylene/organoaluminum LP system is investigated.
Yiling Zhao , Zhikang Chen , Lei Li , Conglei Liu , Hongping Zhu . Silylene/Organoaluminum Lewis Pair System and the Initiation Property for Polymerization of (Meth)acrylates[J]. Chinese Journal of Organic Chemistry, 2023 , 43(10) : 3590 -3597 . DOI: 10.6023/cjoc202305019
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