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1 Supporting Information Highly Active ansa-(fluorenyl)(amido)titanium-based Catalysts with Low Load of Methylaluminoxane for Syndiotactic-Specific Living Polymerization of Propylene Yanjie Sun, Bo Xu, Takeshi Shiono,*, Zhengguo Cai*, State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai , P. R. China Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima, , Japan S1
2 EXPERIMENTAL SECTION Materials All operations were carried out under a nitrogen atmosphere using standard Schlenk techniques or glovebox, and all solvents were purified by PS-MD-5 (INNOVATIVETECHNOLOGY) solvent purification system. A research grade ethylene and propylene were purified by passing them through dehydration column of ZHD-20 and deoxidation column of ZHD-20A before use. MMAO was donated by Tosoh-Finechem Co. The Ti complexes were prepared according to the literature procedure. 1 Polymerization Procedure Polymerization was performed in a 100 ml glass reactor equipped with a magnetic stirrer and carried out as the following two methods. (1) Semi-batch method. At first, the reactor was charged with prescribed amounts of MMAO/BHT and solvent (heptane). After the solution of cocatalyst was saturated with gaseous propylene under atmospheric pressure, polymerization was started by the addition of 1ml solution of the Ti complex (10 or 20 µmol) in heptane, and the consumption rate of propylene was monitored by a mass flow meter. (2) Batch-type method. For the synthesis of block copolymers, after a certain amount of gaseous propylene was dissolved in the heptane solution of MMAO/BHT, polymerization was started by the addition of 1 ml solution of catalyst (10 µmol) in heptanes. After the thirty-minute homopolymerization of propylene, a prescribed amount of propylene of ethylene was added and block copolymerization was conducted for another thirty-minutes and terminated with acidic methanol. The polymers obtained were adequately washed with methanol and dried under vacuum at 80 ºC for 6 h to be a constant weight. Analytical procedure Single crystal of complex was obtained from a solution of hexane at 30 C. The single crystals were mounted under nitrogen atmosphere at low temperature, and data collection was made on a Bruker APEX2 diffractometer using graphite monochromated with Mo Ka radiation (λ= Å). The SMART program package was used to determine the unit cell parameters. The absorption correction was applied S2
3 using SADABS program. 2 All structures were solved by direct methods and refined on F 2 by full-matrix least-squares techniques with anisotropic thermal parameters for non-hydrogen atoms. Hydrogen atoms were placed at calculated positions and were included in the structure calculation. Calculations were carried out using the SHELXS-97, SHELXL-2014 or Olex2 program. 3 Crystallographic data are summarized in Table 1, and CIF files and check are provided in the Supporting Information. Molecular weights and molecular weight distributions of polymers were measured by a polymer laboratory PL GPC-220 chromatograph equipped one PL column and two PL MIXED-B mm columns at 150 ºC using 1, 2, 4-trichlorobenzene as a solvent and calibrated by polystyrene standards. The parameters for universal calibration were K = , α = 0.75 for polystyrene standard and K = , α = 0.78 for PP samples. All 13 C NMR spectra of the polymers were recorded a Bruker Ascend Tm 400 spectrometer at 110 ºC using 1, 1, 2, 2-tetrachloroethane-d 2 as a solvent and the central peak of the solvent (74.47 ppm) was used as an internal reference. The melting temperatures (T m ) of the polymers were measured with a TA Differential Scanning Calorimeter Q2000 in a heating rate of 10 ºC/min from 20~200. [(1-Adamantyl)NSiMe 2 (2, 7-di-t-BuFlu)]TiMe 2 (1a) 1. (2, 7-di-t-BuFlu)SiMe 2 (1-Adamantyl)NH Step A. n-buli (2.4 mol/l, 16.5 mmol) was added dropwise at 0 C in to a solution of 2.32g (15.0 mmol) of 1-Adamantyl in 50 ml of diethylether, and the reaction mixture was stirred for 6 h at r.t. Step B. The product obtained in step A was added at 0 C to a solution of 5.55 g (15.0 mmol) of (2,7-di-t-BuFlu)SiMe 2 Cl in 60 ml of diethlyether, and the resultant yellow suspension was stirred for over night at r.t. The solvent was removed in vacuo and the residue was extracted with hexane. The removal of the hexane gave (1-Adamanty)NHSiMe 2 (2,7-di-t-BuFlu) as an orange solid; 5.42 g, yield 74.2%. S3
4 1 H NMR (CDCl 3 ): δ = 7.75 (d,2h,flu); 7.60 (s,2h,flu); 7.40 (dd,2h,flu); 3.91 (s,1h,9-flu); 2.07 (s,3h,ad); 1.62 (d,6h,ad); 1.59 (d,6h,ad); 1.41 (s,18h,t-bu-flu); 0.91 (s,1h,nh); (s,6h,sich 3 ). 2. [(1-Adamantyl)NSiMe 2 (2, 7-di-t-BuFlu)]TiMe 2 (1a) MeLi (1.6 M in ether 11.2 ml, 18 mmol) was added dropwise at 20 C to a solution of (2, 7-di-t-BuFlu)SiMe 2 (1-Adamantyl) (1.94 g, 4 mmol) in 60 ml of diethylether. The resultant orange solution was stirred at r.t. for 4 h. To a solution of TiCl 4 (0.45 ml, 4 mmol) in 30 ml pentane was added the diethylether solution of the lithium salt, which gave a dark suspension (exothermic reaction with gas evolution). After stirring for 12 h, the solvent was dried in vacuo and the residue was extracted with hexane. Then the hexane solution was concentrated and cooled to 30 C obtaining 0.67 g (1.16 mmol) of FluTi 1a as red crystals in a 29% yield. 1 H NMR (CDCl 3 ): δ=8.01 (d,2h,flu); 7.63 (s,2h,flu); 7.53 (dd,2h,flu); 2.09 (s, 3H,Ad); 1.96 (d, 6H, Ad); 1.67 (d,6h, Ad); 1.37 (s,18h, t-bu-flu); 0.85 (s,6h,sich 3 ); (s,6h,tich 3 ). 13 C NMR (CDCl 3 ): (Flu); (Flu); (Flu); (Flu); (Flu); (Flu); 59.8 (Flu); 54.9 (Ti-(CH 3 ) 2 ); 47.5 (Ad); 36.5 (Ad); 35.3 (Flu-(C(CH 3 ) 3 ) 2 ); 31.5 (Ad); 31.4 (Flu-(C(CH 3 ) 3 ) 2 ); 30.6 (Ad); 6.5 (Si-(CH 3 ) 2 ). C 35 H 51 NSiTi Elemental analysis (calc/found, %): C, 74.83/74.63; H, 9.15/9.14; N, 2.49/2.42. [(1-Adamantyl)NSiMe 2 (3, 6-di-t-BuFlu)]TiMe 2 (1b) 1. (3, 6-di-t-BuFlu)SiMe 2 (1-Adamantyl)NH (3, 6-di-t-BuFlu)SiMe 2 (1-Adamantyl)NH was synthesized in a similar way in 91% yield. 1 H NMR (CDCl3); δ= 7.90 (s, 2H, Flu) ; 7.50 (d, 2H, Flu); 7.37 (dd, 2H, Flu); 3.86 (s, 1H, 9-Flu); 2.16 (s, 3H, Ad); 1.97 (d, 6H, Ad); 1.70 (d, 6H, Ad); 1.44 (s, 18H, t-bu-flu); 0.91 (s, 1H, NH) ; (s, 6H, SiCH 3 ). 2. [(1-Adamantyl)NSiMe 2 (3, 6-di-t-BuFlu)]TiMe 2 (1b) Complex 1b was synthesized in a similar way to that for 1a, and red crystals were obtained in 26% yield. 1 H NMR (CDCl 3 ): δ=8.06 (s, 2H, Flu); 7.60 (d, 2H, Flu); 7.41 (dd, 2H, Flu); 2.08 (s, S4
5 3H, Ad); 1.94 (d, 6H, Ad); 1.66 (d, 6H, Ad); 1.46 (s, 18H, t-bu-flu); 0.81 (s, 6H, SiCH 3 ); (s, 6H, TiCH 3 ). 13 C NMR (CDCl 3 ): (Flu); (Flu); (Flu); (Flu); (Flu); (Flu); 59.8 (Flu); 54.9 (Ti-(CH 3 ) 2 ); 47.6 (Ad); 36.5 (Ad); 35.2 (Flu-(C(CH 3 ) 3 ) 2 ); 32.0 (Ad); 31.9 (Flu-(C(CH 3 ) 3 ) 2 ); 30.6(Ad); 6.4 (Si-(CH 3 ) 2 ). C 35 H 51 NSiTi Elemental analysis (calc/found, %): C, 74.83/74.55; H, 9.15/9.12; N, 2.49/2.20. [t-bunsime 2 (3, 6-di-methoxy-Flu)]TiMe 2 (2a) 1. (3, 6-di-methoxy-Flu)SiMe 2 (t-bunh) (3, 6-di-methoxy-Flu)SiMe 2 (t-bunh) was synthesized in a similar way in 93% yield. 1 H NMR (CDCl 3 ): δ=7.48 (d, 2H, Flu); 7.37 (d, 2H, Flu); 6.94 (dd, 2H, Flu); 3.94 (s, 6H, methoxy-flu); 1.22 (s, 9H, N-t-Bu); 1.21 (s, 1H, NH); (s, 6H, SiCH 3 ). 2. [ t-bunsime 2 (3,6-di-methoxy-Flu)]TiMe 2 (2a) Complex 2a was synthesized in a similar way to that for 1a, and red crystals were obtained in 36% yield. 1 H NMR (CDCl 3 ): δ=7.57 (d, 2H, Flu); 7.35 (d, 2H, Flu); 7.04 (dd, 2H, Flu); 3.99 (s, 6H, methoxy-flu); 1.43 (s, 9H, t-bu- N); 0.78 (s, 6H, SiCH 3 ); (s, 6H, TiCH 3 ). 13 C NMR (CDCl 3 ): (Flu); (Flu); (Flu); (Flu); (Flu); (Flu); 58.6 (Flu); 55.7 (Flu-(OCH 3 ) 2 ); 54.6 (Ti-(CH 3 ) 2 ); 34.5 (N-(C(CH 3 ) 3 ) 2 ); 34.4 (N-(C(CH 3 ) 3 ) 2 ); 5.7 (Si-(CH 3 ) 2 ). C 23 H 33 NO 2 SiTi Elemental analysis (calc/found, %): C, 64.02/63.71; H, 7.71/7.55; N, 3.25/2.79. [(1-Adamantyl)NSiMe 2 (3,6-di-methoxy-Flu)]TiMe 2 (2b) 1. (3, 6-di-methoxy-Flu)SiMe 2 (1-Adamantyl)NH (3, 6-di-methoxy-Flu)SiMe 2 (t-bunh) was synthesized in a similar way in 93% yield. 1 H NMR (CDCl 3 ): δ=7.75 (d, 2H, Flu); 7.60 (d, 2H, Flu); 7.40 (dd, 2H, Flu); 3.91 (s, 1H, 9-Flu); 2.07 (s, 3H, Ad); 1.62 (d, 6H, Ad); 1.59 (d, 6H, Ad); 1.41 (s, 18H, t-bu-flu); 0.91 (s, 1H, NH); (s, 6H, SiCH 3 ). 2. [(1-Adamantyl)SiMe 2 (3, 6-di-methoxy-Flu)]TiMe 2 (2b) Complex 2b was synthesized in a similar way to that for 1a, and red crystals were S5
6 obtained in 30% yield. 1 H NMR (CDCl 3 ); δ=7.57 (d, 2H, Flu); 7.35 (d, 2H, Flu); 7.03 (dd, 2H, Flu); 3.99 (s, 6H, methoxy-flu); 2.09 (s, 3H, Ad); 1.96 (d, 6H, Ad); 1.67(d, 6H, Ad) ; 0.79 (s, 6H, SiCH 3 ); (s, 6H, TiCH 3 ). 13 C NMR (CDCl 3 ): (Flu); (Flu); (Flu); (Flu); (Flu); (Flu); 59.8 (Flu); 55.7 (Flu-(OCH 3 ) 2 ); 54.6 (Ti-(CH 3 ) 2 ); 47.6 (Ad); 36.5 (Ad); 31.7 (Ad); 30.6 (Ad); 6.2 (Si-(CH 3 ) 2 ). C 29 H 39 NO 2 SiTi Elemental analysis (calc/found, %): C, 68.35/68.59; H, 7.71/7.49; N, 2.75/2.66. Table S1. Crystallographic Date and parameters for 1a, 2a, 2b. Complex 1a 2a 2b formula C 35 H 51 NSiTi C 23 H 33 NO 2 SiTi C 29 H 39 NO 2 SiTi formula weight crystal system Triclinic Triclinic Orthorhombic space group P -1 P -1 P b c a a (Å) (8) 8.216(2) (11) b (Å) (8) (2) (3) c (Å) (11) (2) (4) β(deg) (10) (7) 90 V(Å 3 ) (2) (4) (12) Z Density (calculated) Mg/m Mg/m Mg/m 3 F(000) Theta range for data collection to to to Reflections collected Independent reflections Final R indices [I>2sigma(I)] [R(int)= ] [R(int) = ] [R(int) = ] R1 = , R1 = , R1 = , wr2 = wr2 = wr2 = S6
7 Table S2.Results of post polymerization of propylene and propylene with ethylene a entry monomer (g) time (min) yield (%) M n b ( 10 4 ) M w /M n b N c (µmol) Tm d ( ) 18 P P P P 0.60g + E 1.57g a Polymerization conditions: solvent = 100 ml toluene, Ti = 10 µmol, propylene, ethylene = 1 atm, 25 C. b Number-average molecular weight and molecular weight distribution determined by GPC using universal calibration. c Calculated from yield and M n. d Determined by DSC. Figure S1. 13 C HMR spectrum of propylene-ethylene block copolymer. S7
8 P C C C S T n T P S Figure S2. 13 C HMR spectrum of polypropylene obtained with 1a. mmmm mmmr rmmr mmrr mmrm + rmrr rmrm rrrr mrrr mrrm Figure S3. 13 C HMR spectrum of the methyl region of polypropylene obtained with 1a. S8
9 P C C C S T n T P S Figure S4. 13 C HMR spectrum of polypropylene obtained with 1b. mmmm mmmr rmmr mmrr mmrm + rmrr rmrm rrrr mrrr mrrm Figure S5. 13 C HMR spectrum of the methyl region of polypropylene obtained with 1b. S9
10 P C C C S T n T P S Figure S6. 13 C HMR spectrum of polypropylene obtained with 2a. mmmm mmmr rmmr mmrr mmrm + rmrr rmrm rrrr mrrr mrrm Figure S7. 13 C HMR spectrum of the methyl region of polypropylene obtained with 2a. S10
11 P C C C S T n T P S Figure S8. 13 C HMR spectrum of polypropylene obtained with 2b. mmmm mmmr rmmr mmrr mmrm + rmrr rmrm rrrr mrrr mrrm Figure S9. 13 C HMR spectrum of the methyl region of polypropylene obtained with 2b. S11
12 REFRENCES (1) Nishii, K.; Hagihara, H.; Ikeda, T.; Shiono T. J. Organomet. Chem. 2006, 691, (2) Sheldrick, G. M. SADABS: An Empirical Absorption Correction Program for Area Detector Data. University of Göttingen: Göttingen, Germany, (3) (a) Sheldrick, G. M. Acta Cryst. 2008, A64, (b) Sheldrick, G. M. A short history of SHELX. Acta Cryst. 2015, C71, 3-8. (c) Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J. J. Appl. Cryst. 2009, 42, (d) SAINT+, Vdrsion 6.22a; Bruker AXS Inc.: Madison, WI, (e) SAINT+, Vdrsion v7.68a; Bruker AXS Inc.: Madison, WI, (f) SHELXTL NT/2000, Version 6.1; Bruker AXS Inc.: Madison, WI, (g) Sheldrick, G. M. Acta Crystallogr. Scet. C: Struct. Chem. 2015, 71, 3-8. S12
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