Facile strategy to well-defined water-soluble boronic acid (co)polymers

被引:137
作者
Cambre, Jennifer N. [1 ]
Roy, Debashish [1 ]
Gondi, Sudershan R. [1 ]
Sumerlin, Brent S. [1 ]
机构
[1] So Methodist Univ, Dept Chem, Dallas, TX 75275 USA
关键词
D O I
10.1021/ja074239s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile route to well-defined boronic acid (co)polymers from stable and easily manipulated boronic ester monomers is presented. The polymerization of 4-pinacolatoborylstyrene by reversible addition-fragmentation chain transfer (RAFT) yielded polymeric boronic acid precursors. Selection of stoichiometry allowed tuning of polymerization kinetics and targeting specific molecular weights in the range of M-n = 17000-32000 g/mol. The resulting low polydispersity poly(4-pinacolatoborylstyrene) homopolymers were employed as macro-chain transfer agents for block copolymerization with N,N-dimethylacrylamide to yield amphiphilic block copolymers that formed micelles in aqueous media. The pinacol ester derivatized (co)polymers were easily deprotected by a mild and convenient strategy to yield free boronic acid polymers.
引用
收藏
页码:10348 / +
页数:3
相关论文
共 21 条
[1]   Living free-radical polymerization by reversible addition-fragmentation chain transfer: The RAFT process [J].
Chiefari, J ;
Chong, YK ;
Ercole, F ;
Krstina, J ;
Jeffery, J ;
Le, TPT ;
Mayadunne, RTA ;
Meijs, GF ;
Moad, CL ;
Moad, G ;
Rizzardo, E ;
Thang, SH .
MACROMOLECULES, 1998, 31 (16) :5559-5562
[2]   BROMINATION AND LITHIATION - 2 IMPORTANT STEPS IN FUNCTIONALIZATION OF POLYSTYRENE RESINS [J].
FARRALL, MJ ;
FRECHET, JMJ .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (24) :3877-3882
[3]  
Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548
[4]   Borylated polyolefins and their applications [J].
Jäkle, F .
JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2005, 15 (03) :293-307
[5]  
James TD, 2002, TOP CURR CHEM, V218, P159
[6]   SENSITIVE GLUCOSE-INDUCED CHANGE OF THE LOWER CRITICAL SOLUTION TEMPERATURE OF POLY[N,N-DIMETHYLACRYLAMIDE-CO-3-(ACRYLAMIDO)PHENYL-BORONIC ACID] IN PHYSIOLOGICAL SALINE [J].
KATAOKA, K ;
MIYAZAKI, H ;
OKANO, T ;
SAKURAI, Y .
MACROMOLECULES, 1994, 27 (04) :1061-1062
[7]   Totally synthetic polymer gels responding to external glucose concentration: Their preparation and application to on-off regulation of insulin release [J].
Kataoka, K ;
Miyazaki, H ;
Bunya, M ;
Okano, T ;
Sakurai, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (48) :12694-12695
[8]   POLYMERIZATION OF METHYL-METHACRYLATE WITH THE CARBON-TETRACHLORIDE DICHLOROTRIS(TRIPHENYLPHOSPHINE)RUTHENIUM(II) METHYLALUMINUM BIS(2,6-DI-TERT-BUTYLPHENOXIDE) INITIATING SYSTEM - POSSIBILITY OF LIVING RADICAL POLYMERIZATION [J].
KATO, M ;
KAMIGAITO, M ;
SAWAMOTO, M ;
HIGASHIMURA, T .
MACROMOLECULES, 1995, 28 (05) :1721-1723
[9]   ARYLBORONIC ACIDS .3. PREPARATION AND POLYMERIZATION OF PARA-VINYLBENZENEBORONIC ACID [J].
LENNARZ, WJ ;
SNYDER, HR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (09) :2169-2171
[10]   ORGANOBORON COMPOUNDS .10. POPCORN POLYMERS AND HIGHLY CROSS-LINKED VINYL POLYMERS CONTAINING BORON [J].
LETSINGER, RL ;
HAMILTON, SB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (12) :3009-3012