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Organocatalytic Synthesis of Quinine-Functionalized Poly(carbonate)s
Edward, Justin A.,Kiesewetter, Matthew K.,Kim, Hyunuk,Flanagan, James C.A.,Hedrick, James L.,Waymouth, Robert M. American Chemical Society 2012 Biomacromolecules Vol.13 No.8
<P>The ring-opening polymerization of substituted cyclic carbonates with 1-(3,5-bis-trifluoromethyl-phenyl)-3-cyclohexyl-thiourea (TU)/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) organocatalysts afford highly functionalized oligocarbonates. The fluorescent alkaloid quinine can be readily incorporated into the oligocarbonates either by initiation from quinine or by ring-opening polymerization of a quinine-functionalized cyclic carbonate (MTC-Q). Copolymerization of MTC-Q with a boc-protected guanidinium cyclic carbonate affords, after deprotection, highly water-soluble cationic copolymers functionalized with both quinine and pendant guanidinium groups. When multiple quinine groups are attached to the oligomers, they exhibit minimal fluorescence due to self-quenching. Upon hydrolysis, the fluorescence intensity increases, providing a potential strategy for monitoring the hydrolysis rates in real time.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/bomaf6/2012/bomaf6.2012.13.issue-8/bm300718b/production/images/medium/bm-2012-00718b_0004.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/bm300718b'>ACS Electronic Supporting Info</A></P>