o-Benzenedisulfonimide as a recyclable cationic organocatalyst for the controlled/living ring-opening polymerization of δ-valerolactone and ε-caprolactone

被引:36
作者
Jin, Yu [1 ]
Ji, Yufeng [1 ]
He, Xiaojiang [1 ]
Kan, Suli [1 ]
Xia, Haidong [1 ]
Liang, Binqi [1 ]
Chen, Jia [1 ]
Wu, Hao [1 ]
Guo, Kai [1 ]
Li, Zhenjiang [1 ]
机构
[1] Nanjing Univ Technol, State Key Lab Mat Oriented Chem Engn, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Jiangsu, Peoples R China
基金
高等学校博士学科点专项科研基金; 国家高技术研究发展计划(863计划);
关键词
N-HETEROCYCLIC CARBENES; ORGANIC CATALYSTS; ACTIVATED MONOMER; LIVING POLYMERIZATION; ACID CATALYST; EFFICIENT; BLOCK; CARBONATE; LACTONES;
D O I
10.1039/c3py01613g
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
o-Benzenedisulfonimide(OBS) was demonstrated for the first time to be a safe, recyclable, and water-tolerant Bronsted acidic catalyst for the ring-opening polymerization (ROP) of delta-valerolactone and epsilon-caprolactone using benzyl alcohol as the initiator. The polymerizations proceeded to afford poly(delta-valerolactone) and poly(epsilon-caprolactone) with controlled molecular weights and narrow polydispersities. The kinetics and chain extension experiments were carried out to confirm the controlled/living fashion of the polymerizations. In addition, H-1 NMR and MALDI-TOF MS measurements strongly indicated that the initiator residue was incorporated into the obtained polymers. Furthermore, well-defined poly(delta-valerolactone)-block-poly(epsilon-caprolactone) has been successfully synthesized via OBS-catalyzed ROP.
引用
收藏
页码:3098 / 3106
页数:9
相关论文
共 47 条
[1]   Recent developments in ring opening polymerization of lactones for biomedical applications [J].
Albertsson, AC ;
Varma, IK .
BIOMACROMOLECULES, 2003, 4 (06) :1466-1486
[2]   o-benzenedisulfonimide as reusable Bronsted acid catalyst for acid-catalyzed organic reactions [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Dughera, Stefano ;
Venturello, Paolo .
SYNTHESIS-STUTTGART, 2008, (09) :1379-1388
[3]   o-benzenedisulfonimide:: A novel and reusable catalyst for acid-catalyzed organic reactions [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Dughera, Stefano ;
Venturello, Paolo .
SYNLETT, 2007, (14) :2209-2212
[4]   An environmentally friendly Mukaiyama aldol reaction catalyzed by a strong Bronsted acid in solvent-free conditions [J].
Barbero, Margherita ;
Bazzi, Stefano ;
Cadamuro, Silvano ;
Dughera, Stefano ;
Magistris, Claudio ;
Smarra, Alessandra ;
Venturello, Paolo .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2192-2197
[5]   o-Benzenedisulfonimide as a reusable acid catalyst for an easy, efficient, and green synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines through Pictet-Spengler reaction [J].
Barbero, Margherita ;
Bazzi, Stefano ;
Cadamuro, Silvano ;
Dughera, Stefano .
TETRAHEDRON LETTERS, 2010, 51 (48) :6356-6359
[6]   o-Benzenedisulfonimide as a Powerful and Recyclable Organocatalyst for the Nazarov Reaction [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Deagostino, Annamaria ;
Dughera, Stefano ;
Larini, Paolo ;
Occhiato, Ernesto G. ;
Prandi, Cristina ;
Tabasso, Silvia ;
Vulcano, Rosaria ;
Venturello, Paolo .
SYNTHESIS-STUTTGART, 2009, (13) :2260-2266
[7]   o-Benzenedisulfonimide as a Soft, Efficient, and Recyclable Catalyst for the Acylation of Alcohols, Phenols, and Thiols under Solvent-Free Conditions: Advantages and Limitations [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Dughera, Stefano ;
Venturello, Paolo .
SYNTHESIS-STUTTGART, 2008, (22) :3625-3632
[8]   o-Benzenedisulfonimide as a Reusable Bronsted Acid Catalyst for Ritter-Type Reactions [J].
Barbero, Margherita ;
Bazzi, Stefano ;
Cadamuro, Silvano ;
Dughera, Stefano .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (03) :430-436
[9]   Direct organocatalytic ring-opening polymerizations of lactones [J].
Casas, J ;
Persson, PV ;
Iversen, T ;
Córdova, A .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1087-1089
[10]   Phosphoramidic acid catalyzed controlled/living ring-opening polymerization of trimethylene carbonate [J].
Chen, Jia ;
Kan, Suli ;
Xia, Haidong ;
Zhou, Feng ;
Chen, Xing ;
Jiang, Xiaoqin ;
Guo, Kai ;
Li, Zhenjiang .
POLYMER, 2013, 54 (16) :4177-4182