期刊
MACROMOLECULAR RAPID COMMUNICATIONS
卷 43, 期 6, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/marc.202100808
关键词
degradable; organocatalysis; poly(beta-trimethylsilyloxy ester); polyaddition; retro Mukaiyama aldol reaction
资金
- Natural Science Foundation of SZU [000215]
- Shenzhen Science and Technology Research Grant [JCYJ20190808154011907]
- Science and Technology Innovation Commission of Shenzhen [JCYJ20180507182227257]
- Pearl River Talents Plan of Guangdong Province [2017GC010440]
A new type of degradable poly(beta-trimethylsilyloxy ester) was synthesized by the organocatalyzed Mukaiyama aldol polyaddition. These polyesters showed degradation behavior in the presence of nucleophiles, and the degradation mechanism was influenced by the nature of the catalyst used.
Herein, a new type of degradable poly(beta-trimethylsilyloxy ester) prepared by the organocatalyzed Mukaiyama aldol polyaddition between bis(silyl ketene acetal)s and dialdehydes is reported. Specifically, the t-Bu-P-4-catalyzed polyaddition between 1,2-bis[2-methyl-1-(trimethylsiloxy)prop-1-enyloxy]ethane (MTS2) and 4,4'-biphenyldicarboxaldehyde (BPDA) or butane-1,4-diyl bis(4-formylbenzoate) (BDA) can produce poly(beta-trimethylsilyloxy ester)s with number-average molar mass greater than 10 kg mol(-1). For the first time, it is found that these poly(beta-trimethylsilyloxy ester)s are degradable in solution in the presence of nucleophiles such as fluoride and cyanide anions. It is also found that the degradation behavior of poly(beta-trimethylsilyloxy ester)s is highly dependent on the nature of the used catalyst and the bond scission in polymer is fundamentally rooted in the retro Mukaiyama aldol reaction mechanism.
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