The pairing of 1,3-di-tert-butylimidazol-2-ylidene (NHCtBu) and methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) acted as an interacting Lewis pair (ILP) for anionic polymerization of several acrylates. The ILP showed higher polymerization activity for ethyl...

Using scandium triflate [Sc(OTf) 3 ] as a catalyst, chemoselective esterification of tartaric acids by 3-butene-1-ol was performed, and we produced three dialkene monomers: L-di(3-butenyl) tartrate (BTA), D-BTA, and meso-BTA. Thiol−ene polyaddition of these dialkenyl tartrates and dithiols including 1,2-ethanedithiol (ED), ethylene bis(thioglycolate) (EBTG), and D,L-dithiothreitol (DTT) proceeded in toluene at 70 °C under nitrogen to give tartrate-containing poly(ester-thioether)s (M n , (4.2−9.0) × 10 3 ; molecular weight distribution (M w /M n ), 1.6−2.5). In differential scanning calorimetry, the poly(ester-thioether)s showed single T g s between −25 and −8 °C. In biochemical oxygen demand (BOD) tests using activated sludge, poly(L-BTA-alt-EBTG) and poly(L-BTA-alt-ED) showed 32 and 8% biodegradability, which is comparable to that of similar L-malatecontaining poly(ester-thioether)s (23 and 13% biodegradation, respectively). Notably, we observed enantio and diastereo effects on biodegradation because poly(L-BTA-alt-EBTG), poly(D-BTA-alt-EBTG), and poly(meso-BTA-alt-EBTG) showed different degradation behaviors during the biodegradation test (BOD/theoretical oxygen demand (TOD) values after 28 days, 32, 70, and 43%, respectively). Our findings provide insights into the design of biomass-based biodegradable polymers containing chiral centers.

Catenane formation occurs by two-step polymerization of ethyl sorbate (ES), in which, after complete monomer consumption in toluene followed by purification by reprecipitation, a second addition of ES monomer in another pot results in formation of polycatenane.

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