RADICAL CHAIN POLYMERIZATION in .NET

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RADICAL CHAIN POLYMERIZATION
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Living radical polymerizations include atom-transfer radical polymerization (ATRP) and stable free-radical polymerization (SFRP), which proceed with reversible termination, and reversible addition fragmentation transfer (RAFT), which proceeds with reversible chain transfer. Until the extensive exploration of these living polymerizations starting in the mid-1990s, radical polymerization was thought to be a mature process with relatively little left to discover. There is an ongoing effort to exploit the synthetic possibilities of living radical polymerization. Much of the driving force for the effort derives from the belief that wellde ned materials from living radical polymerization will offer substantial advantages to build nanostructures for microelectronics, biotechnology, and other areas. 3-15b 3-15b-1 Atom Transfer Radical Polymerization (ATRP) Polymerization Mechanism
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ATRP, SFRP, and RAFT differ in the method of radical generation. Radical generation in atom-transfer radical polymerization involves an organic halide undergoing a reversible redox process catalyzed by a transition metal compound such as cuprous halide [Kamigaito et al., 2001; Lutz and Matyjaszewski, 2002; Matyjaszewski, 1998a,b, 2002; Matyjaszewski and Xia, 2001; Nanda and Matyjaszewski, 2003; Patten and Matyjaszewski, 1998, 1999; Wang and Matyjaszewski, 1995a; Yoshikawa et al., 2003]. ATRP proceeds as described in Eqs. 3-219 through 3-221:
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R Br + CuBr(L)
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+ CuBr2(L)
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3-219
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CuBr2(L)
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3-220
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3-221
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where L is a ligand that complexes with the cuprous salt and helps to solubilize it in the organic reaction system. ka are kd are rate constants for activation and deactivation of the halide initiator, with K ka =kd . Activation of the initiator involves the CuBr metal center undergoing an electron transfer with simultaneous halogen atom abstraction and expansion of its coordination sphere. R is the reactive radical that initiates polymerization. CuBr2 (L) is the persistent (metallo)radical that reduces the steady-state concentration of propagating radicals and minimizes normal termination of living polymers. The initiator and persistent (metallo)radical are also called the activator and deactivator, respectively. The free-radical nature of ATRP is well established through a number of studies [Matyjaszewski et al., 2001]. The effects of inhibitors and retarders, solvents, and chaintransfer agents are the same in ATRP as in conventional radical polymerization. The regioselectivity, stereoselectivity, and copolymerization behaviors are also the same. The concentration of propagating radicals in ATRP is obtained as
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LIVING RADICAL POLYMERIZATION
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from the equilibrium expression for Eq. 3-219. Combination with the expression for propagation (Eq. 3-22) yields the polymerization rate as
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where I is the initiator, RBr in this case. The polymerization rate is expressed as the change in monomer concentration with time:
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A successful ATRP requires fast and quantitative initiation (activation of RBr) so that all propagating species begin growth at the same time, which results in a narrow molecular weight distribution. Rapid reversible deactivation of propagating radicals is needed to maintain low radical concentrations and minimize normal termination of living polymers. This further ensures a narrow molecular weight distribution because all propagating chains grow at the same rate and for the same length of time. The number-average degree of polymerization for a living polymerization under these conditions is given by
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where M 0 and I 0 are initial concentrations of monomer and initiator, respectively. [M] and p are the monomer concentration and fractional conversion of monomer at any time in the reaction. The number-average degree of polymerization is M 0 = I 0 at complete conversion.
Fig. 3-21 Plots of ln([M]0 /[M]) versus time for ATRP polymerizations of styrene at 110 C with CuBr, 1-phenylethyl bromide (I), and 4,4-di-5-nonyl-2,20 -bipyridine (L). Bulk polymerization (*): M 8:7 M, CuBr 0 L 0 =2 I 0:087 M; Solution polymerization in diphenyl ether (*): M 4:3 M, CuBr 0 L 0 =2 I 0:045 M. After Matyjaszewski et al. [1997] (by permission of American Chemical Society, Washington, DC); an original plot, from which this gure was drawn, was kindly supplied by Dr. K. Matyjaszewski.