Polymers from sugars and CS₂: ring opening copolymerisation of a d-xylose anhydrosugar oxetane

Abstract

A ᴅ-xylose anhydro sugar derivative (1) has been applied in ring-opening copolymerisation (ROCOP) with CS2 to form a polythiocarbonate (poly(CS2-co-1)) with high head-head/tail-tail regioselectivity towards alternating thiono- and trithiocarbonate linkages...

Lithium achieves sequence selective ring-opening terpolymerisation (ROTERP) of ternary monomer mixtures

“…MALDI-TOF analysis unfortunately only led to decomposition of the materials and no signals could be identified as previously reported for sulfur-rich polymers. 26,38 Nevertheless 1 H NMR allows some conclusions regarding the topology as both for LiHMDS or LiOBn initiation, resonances for the HMDS and OBn groups can be identified to be part of the purified polymers. Insertion of alkalimetal alkoxides and amides into CS 2 yielding alkali dithiocarbonates and dithiocarbamates have been previously reported.…”

“…[15][16][17] Sulfur analogous are also accessible such as polythiocarbonate from CS 2 /(epoxide or thiirane) and polythioesters from thioanhydride/(epoxide or thiirane) ROCOP. [18][19][20][21][22][23][24][25][26][27][28][29][30][31] Such sulfur rich polymers are attractive high-refractive index materials that can show improved crystallinity and degradability over their all-oxygen analogues and in some cases enable chemical polymer to monomer recycling. [32][33][34][35][36][37][38][39] Most relevant to this study is a report by Werner and coworkers on lithium alkoxide catalysed CS 2 /epoxide ROCOP yielding poly(monothio-alt-trithiocarbonate)s featuring R-O-C(]S)-O-R and R-S-C(]S)-S-R links (Fig.…”

“…15–17 Sulfur analogous are also accessible such as polythiocarbonate from CS 2 /(epoxide or thiirane) and polythioesters from thioanhydride/(epoxide or thiirane) ROCOP. 18–31 Such sulfur rich polymers are attractive high-refractive index materials that can show improved crystallinity and degradability over their all-oxygen analogues and in some cases enable chemical polymer to monomer recycling. 32–39…”

Thioanhydride/isothiocyanate/epoxide ring-opening terpolymerisation: sequence selective enchainment of monomer mixtures and switchable catalysis

“…10,19 MALDI-TOF analysis unfortunately only led to decomposition of the materials and no signals could be identified as previously reported for sulfurrich polymers. 22,23 However the OBn initiator can be identified to be part of the purified polymers (Fig. S5 †) suggesting the formation of linear as opposed to cyclic chains.…”

UV degradation of poly(lactic acid) materials through copolymerisation with a sugar-derived cyclic xanthate

“…Two major thiocarbonyl resonances at d C E 194 and 223 ppm, of similar intensity, could be seen and were assigned to a mono-thionocarbonate (C(S)O 2 ) environment and a tri-thiocarbonate environment (C(S)S 2 ), respectively. 12,13 Only a small amount of xanthate linkages (SC(S)O; 1-2%) could be identified from a minor resonance at d C E 214 ppm. 19 While MALDI-ToF mass spectrometry proved unsuccessful to probe further the macromolecular structure of poly(1), a good agreement between M n,NMR (estimated by end-group analysis) and M n,SEC values suggested the absence of major cyclic polymer species.…”