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Photoinduced Topological Transformation of Cyclized Polylactides for Switching the Properties of Homocrystals and Stereocomplexes

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Cyclized poly(L-lactide) (PLLA) and poly(D-lactide) (PDLA) incorporating an o-nitrobenzyl group as a photocleavable linker were synthesized and photoirradiated for topological transformation to form photocleaved linear polylactides. The o-nitrobenzyl group was chosen as it is one of the most widely used photolabile protecting groups due to its prompt removal. Two cyclic PLLA and PDLA with this photocleavable linker were prepared via a Hoveyda-Grubbs catalyzed olefin metathesis, a polymerization known to form highly optically pure polylactides without degradation in the stereochemistry (see scheme). SiliaMetS DMT was used to remove residues of ruthenium.

It was shown that the enthalpy of the photocleaved cyclized polylactides was much lower than that of the linear prepolylactides, hence the crystalline-amorphous interface is more stable for the cyclized polylactides arising from the topology.

Yamamoto, T. et al. Polym. Chem., 2015, 6, 3591 - 3600

 

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  1. SiliaMetS DMT (Dimercaptotriazine) (R79030B)

    SiliaMetS DMT (Dimercaptotriazine) (R79030B)

    SiliaMetS DMT is the silica - bound equivalent of 2,4,6 - trimercaptotriazine (trithiocyanuric acid, TMT). It is a versatile metal scavenger for a variety of metals and the preferred metal scavenger for ruthenium catalysts and hindered Pd complexes. Best scavenger for: As, Ir, Ni, Os, Pd, Pt, Rh, Ru & Se. Good scavenger for: Cd, Co, Cu, Fe, Sc & Zn.

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