title: Organocatalytic synthesis of quinine-functionalized poly(carbonate)s.
abstract: 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.
authors: Department of Chemistry, Stanford University, Stanford, California 94305, United States.
authors: Justin A
authors: JA
authors: Edward
authors: Matthew K
authors: MK
authors: Kiesewetter
authors: Hyunuk
authors: H
authors: Kim
authors: James C A
authors: JC
authors: Flanagan
authors: James L
authors: JL
authors: Hedrick
authors: Robert M
authors: RM
authors: Waymouth
mesh_terms: D019905:Benzyl Alcohol / Q000737:chemistry; D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D058105:Polymerization; D011803:Quinine / Q000737:chemistry
chemical_list: D002254:Carbonates; D006146:Guanidines; D011803:Quinine; D019905:Benzyl Alcohol