4.4. Theoretical Investigations: An Essential Tool for Polymerization Catalysis
Theoretical methods are nowadays, mainly due to the efficiency of the new com- puters and the so-called DFT revolution, able to tackle problems as complicated as catalytic reactions such as polymerizations as well as stereoselectivity (in par- ticular, the tacticity of polymers). Thus,in silicomethods recently became an important and essential tool in polymerization catalysis. Indeed, understanding the key factors that govern the polymerization is crucial to design the best catalyst for a given polymerization, and DFT methods can provide accurate reaction path- ways in agreement with experimental findings. For instance, in the specific case of borohydride catalysts, it was unambiguously theoretically demonstrated that the key issue, in order to be able to target well-defined polymers, is the trapping of the formed BH3molecule. If the BH3moiety is trapped by the carbonyl group, then onlya,o-dihydroxytelechelic polymers are obtained in the case of cyclic monomers, while a poor activity is obtained with MMA. On the other hand, if the BH3molecule can be efficiently trapped either by the solvent, the ancillary ligand or the surface, then one can access a greater diversity of polymers and sub- sequently, of polymer properties. In the same way, theoretical methods are able to accurately account for the tacticity of the polymer and the steric and electronic effects that control the selectivity. In that sense, theoretical investigations, when carried out in close combination with experimental studies, can be considered as an essential tool to understand and foresee the polymerization mechanism.
lactones still remain a largely unexplored domain. Similarly, the efficiency of chiral rare-earth complexes in selectively controlling polymerizations remains an open field of research. Factors governing the stereoselectivity of the poly- merization of polar monomers still remain to be better understood so as to enable access to better controlled polymerization processes and in turn to more original polymers. The access to well-defined copolymers of controlled chemical structure from rare-earth borohydride catalysts has been demon- strated as feasible; yet it is hardly exploited and much remains to be studied especially regarding simultaneous copolymerization. Such fundamental exper- imental (synthetic organometallic and polymer chemistries) and theoretical investigations are thus a prerequisite for developing controlled polymerization processes and subsequently for allowing access to tailored functional (co) polymer materials.
ACKNOWLEDGMENTS
The authors gratefully acknowledge the coworkers whose names appear in the following references for their contribution to this research. S. M. G. most gratefully acknowledges Miche`le Schappacher for her significant contribution to the pioneering investigations on the use of rare-earth borohydride catalysts in the ROP of cyclic esters. The authors are thankful to the Centre National de la Recherche Scientifique (CNRS) (S. M. G.), the Deutsche Forschungsgemeinschaft (DFG) (P. W. R.), and the Institut Universitaire de France (L. M.) for their continuous support.
LIST OF SYMBOLS, ABBREVIATIONS, AND ACRONYMS ALA L-alanineN-carboxyanhydride
Ap*H (2,6-diisopropyl-phenyl)-[6-(2,4,6-triisopropyl- phenyl)-pyridin-2-yl]-amine
Ar (C6H2tBu3-2,4,6)
Benz benzene
rac-BL racemic-b-butyrolactone, (S,S/R,R)-b-butyrolactone BLL e-carboxbenzoxy-L-lysineN-carboxyanhydride BLG g-benzylL-glutamateN-carboxyanhydride
CL e-caprolactone
COT Z8-cyclooctatetraenyl (Z8-C8H8) Cp Z5-cyclopentadienyl (Z5-C5H5)
CpiPr4 tetra-iso-propylcyclopentadienyl (C5HiPr4) CpPh3 1,2,4-triphenylcyclopentadienyl (C5H2Ph3-1,2,4) Cp* Z5-pentamethylcyclopentadienyl (Z5-C5Me5) Cp*Pr tetramethyl-n-propylcyclopentadienyl (C5Me4nPr)
Cy cyclohexyl (C6H11)
DAB2 ((2,6-C6H3i
Pr2)NC(Me)]C(Me)N(2,6-C6H3i
Pr2))2 DCM dichloromethane (CH2Cl2)
Handbook on the Physics and Chemistry of Rare Earths 80
DFT density functional theory
ÐM dispersity (molar mass distribution; Mw/Mn) DME 1,2-dimethoxyethane (MeO(CH2)2OMe) DSC differential scanning calorimetry FTIR Fourier transform infrared spectroscopy HO-polymer-OH a,o-hydroxytelechelic polymer
D-LA D-lactide, (R,R)-lactide LLA L-lactide, (S,S)-lactide
rac-LA racemic-lactide, (D,L)-lactide, (R,R/S,S)-lactide MALDI-ToF matrix-assisted laser desorption/ionization- time-of-
flight
Mes mesityl (C6H2Me3-2,4,6) mm % isotactic triad content
MMA methyl methacrylate
Mn number average molar mass
mr % atactic triad content
MS mass spectrometry
Mw weight average molar mass
Mw/Mn dispersity (ÐM; molar mass distribution)
NCA N-carboxyanhydride
nd not determined
N2NN0 (2-C5H4N)CH2N(CH2-CH2NMe)2
N2NNMes (2-C5H4N)CH2N(CH2CH2N(C6H2Me3-2,4,6))2 N2NNTMS (2-C5H4N)CH2N(CH2CH2N(SiMe3))2
O2NL RCH2N(CH2-2-O-3,5-C6H2tBu2)2where R¼CH2OMe, CH2NMe2, (2-C5H4N), or Et for L¼OMe, NMe2, py, or nPr, respectively
(O2N2)1 {CH2N(Me)CH2-3,5-Me,tBu-C6H2O}2 (O2N2)2 C5H4NCH2Nd{CH2-3,5-Me,tBu-C6H2O}2 PBLG poly(g-benzylL-glutamateN-carboxyanhydride)
PCL poly(e-caprolactone)
PCL-b-PTMC poly(e-caprolactone)-b-poly(trimethylene carbonate) PCL-co-PTMC poly(e-caprolactone)-co-poly(trimethylene carbonate)
PDL o-pentadecalactone
PHB poly(3-hydroxybutyrate)
PLA poly(lactic acid), poly(lactide) PLLA poly(L-lactic acid), poly(L-lactide)
Pm probability ofmesolinkages between monomer units PMMA poly(methyl methacrylate)
Pr probability ofracemic linkages between monomer units
PTMC poly(trimethylene carbonate)
py pyridine (C5H5N)
ROP ring-opening polymerization
rr % syndiotactic triad content
RT room temperature
SEC size exclusion chromatography
@SiO silica grafted
Sn(Oct)2 stannous(2-ethylhexanoate) tetrahydrosalen [(2-OHdC6H2t
Bu2-3,5)CH2N(CH3)CH2]2
Tg glass transition temperature
THF tetrahydrofuran
Tm melting temperature
TMC trimethylene carbonate (3-dioxan-2-one) TMS trimethylsilyl (SiMe3)
TOF turn over frequency, activity p-Tol para-tolyl (p-CH3]C6H4) (p-Tol)NN [(p-CH3C6H4)N(CH3)C]2CH
TptBu,Me tris(2-t-butyl-4-methyl)pyrazolylborate
VL d-valerolactone
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Handbook on the Physics and Chemistry of Rare Earths 86
Structures and Properties of Rare-Earth Molten Salts
Yasuhiko Iwadate
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba, Japan
Chapter Outline