Living Radical Polymerization of N2Vinylamides

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1 PROGRESS IN CHEMISTRY Vol. 20 No. 10 Oct., 2008 N ( ; ) N2,, 2 (RAFT) (MADIX), ( ),, (ATRP) N2 : O : A : X(2008) Living Radical Polymerization of N2Vinylamides Pu Hongting 1 Cai Xiangyu 1 Wan Decheng Yang Genjin 2 (1. Institute of Functional Polymers, School of Materials Science & Engineering, Tongji University, Shanghai , China ; 2. School of Pharmacy, The Second Military Medical University, Shanghai , China) Abstract The progress regarding the living radical polymerization of N2vinylamides (NVAs) is summarized. The living radical polymerization of the unconjugated NVAs once represented a synthetic challenge, but pleasant progress has been made recently in this field. It is found that selected members of the xanthate family and dithiocarbamate family are able to control the polymerization of NVAs via reversible addition2fragmentation chain transfer ( RAFT) polymerization or via the interchange of xanthate (MADIX) under certain conditions, and the tacticity can be simultaneously controlled under specific conditions. The recently developed organobismuth, organostibine and organotellurium compounds are effective mediators for the ( co ) polymerization of most NVAs, expanding the spectra of polymer composition. Additionally, some of the atom transfer radical polymerization (ATRP) systems are applicable to the polymerization of NVAs. Key words N2vinylamides ; living radical polymerization ; organobismuth ; organostibine ; organotellurium 1 N2, N2 (NVF), N2 (NVP) N2 (NVCL), 1,PNVP [1 ] 1 N2 Fig. 1 Chemical structure of several typical N2vinylamides : , : (No ) 3 3 e2mail tongji. edu. cn

2 10 N ; (PEO) 1939,,,, 100,, N2 N2 [1 ], PNVCL,, N2 ( PNIPAM), 32 PNIPAM, PNVCL PNVP,, PNIPAM N2, [1 ], PNVP PNVP,, 2 RAFTΠMADIX,, N2,, 1993 Georges [2 ] (NMP) [3 ], [4 (ATRP) 6 ], [7 2 (RAFT) 9 ] ( MADIX [10 ], RAFT ), N2,,,, N2, 1998 [11 ],, 2002,, N2 RAFTΠMADIX 2 [7,8,10 ] 2 RAFTΠMADIX [7,8,10 ] Fig. 2 Mechanism of RAFTΠMADIX RAFTΠMADIX

3 [12, 16 ] 1 ( Z R ), 2,Z R 3 N2 RAFTΠMADIX ZC( [12 S) SR 18 ] Fig. 3 Chain transfer agents ZC( = S) SR employed in RAFTΠ [12 MADIX polymerization of N2vinylamides 18 ] 2003, [17 ] (PEO) ( 1a, 3), 100 PEO2 PNVF,, (PDI) , [18 ] 1b, 1c 1j, NVP RAFTΠMADIX, 1c, PDI : (1) ; (2), 1j 1, ( ) ( ) 2,5,, ; (3) 1b, 1c, 1c 1b, R NVP,R, [19,20 ] R, ( ) ( ) : R ( ) ( ) P m P n,, 1 [21 ] ; (4), PNVP 1c,, Devasia [22 ] 1e NVP RAFTΠMADIX, ( ), 2 P m R ( R PNVP),,,, P m P n,,,,,,, PNVP Stenzel [19 ], 1b, 1c PNVP Moad [23 ] 1f PNVP,, Klumperman [21 ] 1g NVP 1g,,, 2 ( ), RAFTΠMADIX,1h, NVP,, 1i R,,NVP N2, [24 ] RAFTΠMADIX,, NVP, NVP NVCL [20 ],NVCL

4 10 N ( GPC) (MALTI2TOF),,, GPC MALTI2TOF PNVCL, 1b 1c 1d 1c, 1b 1d, PDI 1150,,,, 1d PDI 1124 ( MALTI2TOF ), 1c NVP, NVCL,,, N2, N2,,, Yamago NVP ( NVCL ), [ 25 3 TERP SBRP BIRP 31], 3 NMP ATRP RAFTΠMADIX,, ATRP RAFTΠ MADIX,, 2002,Yamago [27 29 ], [30,31 ] [25 ] (TERP) (SBRP) (BIRP) 4 [25 31 ] Fig. 4 Chemical compounds of organotellurium,organostibine and organobismuthine that used in living radical [25 polymerization 31 ], 2a 2c 2d 2f 2g 2h, 100, BIRP > SBRP > TERP BIRP, : (1) ( ), ; (2) NVP 2g NVP [25 ], ,PDI 1112 ; (3), [26 ],, (MMA) NVP ( ) [31 ], 2d, AIBN (AIBN 0125 ), 60, PMMA ( M n = 4 700,

5 PDI = 1127), PMMA2b2PNVP (, M n = , PDI = 1131), PNVP( M n = 3 000, PDI = 1. 06), PNVP2b2PMMA (, M n = , PDI = 1. 18),,TERP SBRP BIRP NVP Π [25,27,30,31 ], BIRP > SBRP > TERP, 112 (Me 6 Cyclam),, NVP,, PDI (NMP), Hadjichristidis [38,39 ], NVP,, N2? 5 [25 ],,,, (, 5 ), k ex,, P P,,,, BIRP > SBRP > TERP >, 5 [25 ] Fig. 5 Schematic mechanism of organobismuthine2mediated living radical polymerization [25 ], [32,33 ],, 4 ATRP,, N2,, ATRP,, Debuigne [34 ], NVP [35 ],, PDI 1130 Matyjaszewski [36 ] NVP,, PDI 117 Meng [37 ] 5,5,7,12,12,142 21,4,8,, N2 Π ( RAFTΠMADIX ) ( BIRP SBRP TERP ) ATRP,,,, [ 1 ] Kirsh Y E. Water Soluble Poly2N2Vinylamides, Synthesis and Physicochemical Properties. Chichester : John Wiley & Sons, 1998 [ 2 ] Georges M K, Veregin R P N, Kazmaier P M, et al. Macromolecules, 1993, 26 : [ 3 ] Hawker C J, Bosman A W, Harth E. Chem. Rev., 2001, 101 : [ 4 ] Matyjaszewski K, Xia J. Chem. Rev., 2001, 101 : [ 5 ] Kamigaito M, Ando T, Sawamoto M. Chem. Rev., 2001, 101 : [ 6 ] Percec V, Barboiu B. Macromolecules, 1995, 28 : [ 7 ] Chiefari J, Chong Y K, Ercole F, et al. Macromolecules, 1998, 31 :

6 10 N [ 8 ] Le T P, Moad G, Rizzardo E, et al. Australia, PCT Int. Appl. WO A [ 9 ] Moad G, Rizzardo E, Thang S H. Austra. J. Chem., 2006, 59 : [10] Destarac M, Bzducha W, Taton D, et al. Macromol. Rapid. Commun., 2002, 23 : [11] Chiefari J, Mayadunne R T A, Moad G, Rizzardo E, Thang S H. WO A [12] ( Ge X P), (Bai R K), (Progress in Chemistry), 2007, 19(9) : [13] Lowe A B, McCormick C L. Prog. Polym. Sci. 2007, 32 : [14] Barner L, Davis T P, Stenzel M H, Barner2Kowollik C. Macromol. Rapid Commu., 2007, 28 : [15] Moad G, Rizzardo E, Thang S H. Polymer, 2008, 49 : [16] Moad G, Rizzardo E, Thang S H. Australian J. Chem., 2006, 59 : [17] Shi L J, Chapman T M, Beckman E J. Macromolecules, 2003, 36 : [18] Wan D C, Satoh K, Kamigaito M, et al. Macromolecules, 2005, 38 : [19] Nguyen T L U, Eagles K, Stenzel M H, et al. J. Polym. Sci., Part A : Polym. Chem., 2006, 44 : [20] Wan D C, Zhou Q, Pu H T, et al. J. Polym. Sci., Part A : Poly. Chem., 2008, 46 : [21] Pound G, McLeary J B, McKenzie J M, Lange R F M, Klumperman B. Macromolecules, 2006, 39 : [22] Devasia R, Bindu R L, Borsali R, et al. Macromol. Symp., 2005, 229 : 8 17 [23] Postma A, Davis T P, Moad G, et al. Macromolecules, 2006, 39 : [24] Devasia R, Borsali R, Lecommandoux S, et al. Abstract of Papers of the American Chemcial Society, 2005, 230 : U4231 U4232 [25] Yamago S, Kayahara E, Kotani M, et al. Angew. Chem. Int. Ed., 2007, 46 : [26] Yamago S. J. Polym. Sci., Part A : Polym. Chem., 2006, 44 : 1 12 [27] Yusa S, Yamago S, Sugahara M, et al. Macromolecules, 2007, 40 : [28] Yamago S, Iida K, Yoshida J. J. Am. Chem. Soc., 2002, 124 : [29] Yamago S, Iida K, Yoshida J. J. Am. Chem. Soc., 2002, 124 : [30] Yamago S, Ray B, Iida K, et al. J. Am. Chem. Soc., 2004, 126 : [31] Ray B, Kotani M, Yamago S. Macromolecules, 2006, 39 : [32] Curran D P. in Comprehensive Organic Synthesis. Vol. 4 (eds. : Trost B M. Fleming I). Oxford : Pergamon, [33] Renaud P, Sibi M P. Radicals in Organic Synthesis. Weinheim : Wiley2VCH [34] Debuigne A, Caille J R, Jerome R. Angew. Chem. Int. Ed., 2005, 44 : [35] Debuigne A, Willet N, Jerome R, et al. Macromolecules, 2007, 40 : [36] Kaneyoshi H, Matyjaszeski K. Macromolecules, 2006, 39 : [37] Lu X J, Gong S L, Meng L Z, et al. Polymer, 2007, 48 : [38] Bilalis P, Pitsilalis M, Hadjichristidis N. J. Polym. Sci. Part A : Polym. Chem., 2006, 44 : [39] Bilalis P, Zorba G, Pitsilalis M, Hadjichristidis N. J. Polym. Sci. Part A : Polym. Chem., 2006, 44 :

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