Facile Synthesis of Hybrid Silica Nanoparticles Grafted with Helical Poly(phenyl isocyanide)s and Their Enantioselective Crystallization Ability

• DOI: 10.1021/acs.macromol.6b01870
• Publication Date: 2016-10-05T20:29:36Z
• Authors: Li Yang; Yang Tang; Na Liu; Chun-Hua Liu; Yunsheng Ding; Zong-Quan Wu
• Keywords: Hybrid material; Silanization

In this contribution, we report on the facile synthesis of hybrid silica nanoparticles grafted with helical poly(phenyl isocyanide)s via both "grafting from" and to" strategies. First, triethoxysilanyl functionalized alkyne–Pd(II) initiator was anchored onto surface bare through silanization coupling reaction. Polymerization phenyl isocyanide using Pd(II)–anchored lead to formation isocyanide)s. The surface-initiated polymerization revealed proceed in a living/controlled chain-growth manner, afforded controlled thickness. 31P NMR analysis indicated initiation efficiency surface-anchored Pd(II) initiators is very high, almost quantitative. grafting density determined be ∼0.89 nm2/chain based thermal gravity (TGA). optically active bearing an l-alanine long decyl chain Pd(II)-anchored formed chiral isocyanide) arms preferred handedness. Second, were prepared strategy. Well-defined terminated manners. polymer reaction, isocyanide). TGA indicates ∼0.76 nm2/chain. Taking advantage synthetic method, left-handed nanoparticles, generated high optical activity. Such nanoparticle exhibited good performance enantioselective crystallization racemic Boc-alanine. enantiomeric excess (ee) induced crystal up 95%.