3 years ago

Synthesis of Amphiphilic Helix–Coil–Helix Poly(3-(glycerylthio)propyl isocyanate)-block-polystyrene-block-poly(3-(glycerylthio)propyl isocyanate)

Synthesis of Amphiphilic Helix–Coil–Helix
Poly(3-(glycerylthio)propyl isocyanate)-block-polystyrene-block-poly(3-(glycerylthio)propyl isocyanate)
Chang-Geun Chae, Ho-Bin Seo, Jae-Suk Lee, In-Gyu Bak
To achieve molecular packing of protic-functionalized helical polymers in aqueous solution, we synthesized an amphiphilic helix–coil–helix triblock copolymer (triBCP) composed of polystyrene and dihydroxyl-functionalized polyisocyanates. Poly(3-(glycerylthio)propyl isocyanate)-block-polystyrene-block-poly(3-(glycerylthio)propyl isocyanate), P3GPIC-b-PSt-b-P3GPIC, was synthesized by postpolymerization modification. The bidirectional anionic block copolymerization of styrene (St) and allyl isocyanate (AIC) yielded triBCPs, poly(allyl isocyanate)-block-polystyrene-block-poly(allyl isocyanate)s (PAIC-b-PSt-b-PAICs), with well-controlled molecular weights (Mn = 5.60–99.9 kDa) and narrow dispersities (Đ = 1.14–1.18). Of them, one with the lowest MW (Mn = 5.60 kDa, Đ = 1.14), which was highly organic-soluble, was utilized in the thiol–ene click reaction between allyl group and 1-thioglycerol, producing P3GPIC-b-PSt-b-P3GPIC. The amphiphilic P3GPIC-b-PSt-b-P3GPIC self-aggregated to form spherical vesicles with an average hydrodynamic diameter of 170 nm in aqueous solution, demonstrating that hydrophilic–helical P3GPIC blocks well interacted with water media maintaining their intermolecular packing.

Publisher URL: http://dx.doi.org/10.1021/acs.macromol.7b02619

DOI: 10.1021/acs.macromol.7b02619

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