and Trimethylene Carbonate
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1 Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2018 Supporting information for Preparation of Multiblock Copolymers via Step-wise Addition Polymerization of L-lactide and Trimethylene Carbonate Mark Abubekerov, Junnian Wei, Kevin R. Swartz, Zhixin Xie, Qibing Pei, and Paula L. Diaconescu* Department of Chemistry and Biochemistry, University of California, Los Angeles, CA Table of Contents 1. NMR Spectra S2 2. Conversion Studies S28 3. Size Exclusion Chromatography S30 4. Differential Scanning Calorimetry S37 5. Dynamic Mechanical Analysis S43 6. X-ray Crystallographic Data S49 7. DFT Calculations S50 8. References S148 S1
2 NMR Spectroscopy Figure S1. 1 H NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2: δ (ppm) 2.00 (s, 6H, CH3), 2.47 (s, 6H, CH3), 3.74 (t, 2H, Cp-H), 3.91 (t, 2H, Cp-H), 4.03 (s, 2H, OCH2Ph), 4.13 (q, 2H, Cp- H), 4.32 (t, 2H, Cp-H), 4.88 (br s, 1H, BH), 5.76 (s, 2H, CH), 6.69 (m, 2H, o-ph), 6.81 (m, 2H, m-ph), 6.87 (m, 1H, p-ph), 7.04 (m, 6H, m-ph, p-ph), 7.53 (m, 4H, o-ph). Peaks at 1.12 ppm and 3.27 ppm are attributed to residual diethyl ether. Peaks at 1.42 ppm and 3.58 ppm are attributed to residual tetrahydrofuran. S2
3 Figure S2. 13 C NMR spectrum (C6D6, 126 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2: δ (ppm) 13.5 (s, CH3), 14.0 (d, CH3), 69.9 (s, Cp-C), 70.5 (s, OCH2Ph), 72.7 (d, Cp-C), 74.1 (s, Cp-C), 74.3 (d, Cp-C), 75.7 (d, Cp-C), (s, CH), (s, aromatic), (s, aromatic), (d, aromatic), (d, aromatic), (s, aromatic), (s, CCH3), (s, CCH3). Peaks at 15.9 ppm and 66.3 ppm are attributed to residual diethyl ether. Peaks at 26.2 ppm and 68.2 ppm are attributed to residual tetrahydrofuran. S3
4 Figure S3. 31 P{ 1 H} NMR spectrum (C6D6, 203 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2: δ (ppm) (s). Figure S4. 11 B NMR spectrum (C6D6, 161 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2: δ (ppm) -7.2 (br s). S4
5 Figure S5. 1 H NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ-OH)]2: δ (ppm) (s, 1H, OH), 2.24 (s, 6H, CH3), 2.37 (s, 6H, CH3), 3.40 (t, 2H, Cp-H), 3.48 (t, 2H, Cp-H), 3.99 (q, 2H, Cp-H), 4.21 (t, 2H, Cp-H), 4.69 (br s, 1H, BH), 5.76 (s, 2H, CH), 7.04 (m, 6H, m-ph, p-ph), 7.45 (m, 4H, o-ph). Figure S6: 13 C NMR spectrum (C6D6, 126 MHz, 298 K) of [(fc P,B )Zn(μ-OH)]2: δ (ppm) 13.4 (s, CH3), 13.7 (d, CH3), 69.9 (s, Cp-C), 72.6 (d, Cp-C), 74.5 (s, Cp-C), 74.6 (d, Cp-C), 76.0 (d, Cp-C), (s, CH), (d, aromatic), (d, aromatic), (s, CCH3), (s, CCH3). S5
6 Figure S7. 31 P{ 1 H} NMR spectrum (C6D6, 203 MHz, 298 K) of [(fc P,B )Zn(μ-OH)]2: δ (ppm) (s). Figure S8. 11 B NMR spectrum (C6D6, 161 MHz, 298 K) of [(fc P,B )Zn(μ-OH)]2: δ (ppm) -6.6 (br s). S6
7 Figure S9. Variable temperature NMR (C6D6, 500 MHz) study of [(fc P,B )Zn(μ-OCH2Ph)]2. S7
8 Figure S10. Selected region of 1 H NOESY NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ- OCH2Ph)]2. S8
9 Figure S11. Selected region of 1 H NOESY NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ- OCH2Ph)]2. S9
10 Figure S12. NMR scale reaction (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2 and L-lactide: δ (ppm) 0.94 (d, 3H, CH3(LA)), 1.25 (d, 3H, CH3(LA)), 2.22 (s, 3H, CH3(pz)), 2.37 (s, 3H, CH3(pz)), 2.45 (s, 3H, CH3(pz)), 2.47 (s, 3H, CH3(pz)), 3.53 (q, 1H, CH(LA)), 3.93 (s, 1H, Cp-H), 3.95 (s, 1H, Cp-H), 4.06 (s, 1H, Cp-H), 4.14 (s, 1H, Cp-H), 4.24 (s, 1H, Cp-H), 4.37 (s, 1H, Cp-H), 4.40 (s, 1H, Cp-H), 4.60 (q, 1H, CH(LA)), 4.72 (q, 2H, OCH2Ph), 5.79 (s, 1H, CH(pz)), 5.82 (s, 1H, CH(pz)), 6.95 (m, 2H, o-bn), 7.06 (m, 9H, m-bn, p-bn, m-ph, p-ph), 7.57 (m, 4H, o-ph). S10
11 Figures S13. Variable temperature NMR (C6D6, 500 MHz) study of [(fc P,B )Zn(LA)(OCH2Ph)]2. Figure S14. 1 H NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2 in the presence of 5 equivalent of pyridine. No change in the signals corresponding to [(fc P,B )Zn(μ-OCH2Ph)]2 is observed. S11
12 Figure S15. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2. A minor difference in the diffusion rates of the OCH2Ph component vs. the heteroscorpionate supporting ligand is observed. Such drifts in the signals corresponding to the same molecule can be found in various DOSY spectra in the literature. 1 S12
13 Figure S16. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of (fc P,B )ZnCl. Figure S17. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(LA)(OCH2Ph)]2. S13
14 Figure S18. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(PTMC)36(OCH2Ph)]2. Signals at 4.94 ppm, 7.07 ppm and 7.18 ppm correspond to the -OCH2Ph end group. Signals not on the line are attributed to residual monomer, THF, hexamethylbenzene, and C6D6. Figure S19. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of the PhCH2O(PTMC)36H polymer. Signals at 4.94 ppm, 7.07 ppm and 7.18 ppm correspond to the -OCH2Ph end group. Signals not on the line are attributed to hydrolyzed catalyst, residual monomer, THF, hexamethylbenzene, and C6D6. S14
15 Figure S20. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(PLA)36(OCH2Ph)]2. Signals at 4.72 ppm, 6.95 ppm and 7.06 ppm correspond to the - OCH2Ph end group. Signals not on the line are attributed to residual monomer, THF, hexamethylbenzene, and C6D6. Figure S21. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of PhCH2O(PLA)36H. Signals at 4.72 ppm, 6.95 ppm and 7.06 ppm correspond to the -OCH2Ph end group. Signals not on the line are attributed to hydrolyzed catalyst, residual monomer, THF, hexamethylbenzene, and C6D6. From the DOSY NMR spectra the following the diffusion coefficients were determined: D[(fc P,B )ZnCl] = m 2 /s D = m 2 /s D{[(fc P,B )Zn(LA)(OCH2Ph)]2} = m 2 /s D{[(fc P,B )Zn(PTMC)36(OCH2Ph)]2} = m 2 /s S15
16 D[PhCH2O(PTMC)36H] = m 2 /s D{[(fc P,B )Zn(PLA)36(OCH2Ph)]2} = m 2 /s D[PhCH2O(PLA)36H] = m 2 /s The Stokes-Einstein equation shows the relationship between the hydrodynamic radius and the diffusion coefficient: D = (kt)/(6πηrh) By comparing the diffusion coefficients of two compounds the ratios of the hydrodynamic radii can be determined. D(ZnCl)/D(ZnOBn)2 = r(znobn)2/r(zncl) = 1.63 D(ZnOBn)2/D[Zn(LA)OBn]2 = r[zn(la)obn]2/r(znobn)2 = 1.24 D(PhCH2O(PLA)36H)/D[Zn(PLA)36(OCH2Ph)]2 = r[zn(pla)36(och2ph)]2/r(phch2o(pla)36h) = 1.92 D(PhCH2O(PTMC)36H)/D[Zn(PTMC)36(OCH2Ph)]2 = r[zn(ptmc)36(och2ph)]2/r(phch2o(ptmc)36h) = 1.84 Figure S22. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of PLA-b-PTMC-b-PLA. S16
17 Figure S23. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of PTMC-b-PLA-b-PTMC. Figure S24. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of PTMC-b-PLA-b-PTMC-b-PLA-b- PTMC. S17
18 Figure S25. 1 H DOSY NMR spectrum (C6D6, 500 MHz, 298 K) of PLA-b-PTMC-b-PLA-b-PTMC-b- PLA. Figure S26. Thermal decomposition study (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2, 24 h at ambient temperature. Percent decomposition is calculated based on newly formed pyrazole signals. S18
19 Figure S27. Thermal decomposition study (C6D6, 500 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2, 1.5 h at 70 C. Percent decomposition is calculated based on newly formed pyrazole signals. Figure S28. Thermal decomposition study (C6D6, 300 MHz, 298 K) of [(fc P,B )Zn(μ-OCH2Ph)]2 in the presence of 100 equivalents of L-lactide, 3 h at 70 C. No catalyst decomposition is observed. S19
20 Figure S29. 1 H NMR spectrum (CDCl3, 500 MHz, 298 K) of L-LA polymerization (Table 1, entry 1). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:566. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.23 (s, 18H, CH3 HMB), 5.16 (q, 2H, CHCH3 PLA). Figure S30. 1 H NMR spectrum (CDCl3, 500 MHz, 298 K) of TMC polymerization (Table 1, entry 2). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC ratio is 1:10:202. δ (ppm) 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC). S20
21 Figure S31. 1 H NMR spectrum (CDCl3, 500 MHz, 298 K) of PLA-b-PTMC polymerization (Table 1, entry 3). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:196:608. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). Figure S32. 1 H NMR spectrum (CDCl3, 300 MHz, 298 K) of PTMC-b-PLA polymerization (Table 1, entry 4). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:158:550. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). S21
22 Figure S33. 1 H NMR spectrum (CDCl3, 300 MHz, 298 K) of PTMC-b-PLA-b-PTMC polymerization (Table 1, entry 5). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:170:566. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). Figure S34. 1 H NMR spectrum (CDCl3, 300 MHz, 298 K) of PLA-b-PTMC-b-PLA polymerization (Table 1, entry 6). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:176:606. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). S22
23 Figure S35. 1 H NMR spectrum (CDCl3, 500 MHz, 298 K) of PLA-b-PTMC-b-PLA-b-PTMC polymerization (Table 1, entry 7). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:200:596. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). Figure S36. 1 H NMR spectrum (CDCl3, 500 MHz, 298 K) of PTMC-b-PLA-b-PTMC-b-PLA-b-PTMC polymerization (Table 1, entry 8). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:192:628. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). S23
24 Figure S37. 1 H NMR spectrum (CDCl3, 500 MHz, 298 K) of PLA-b-PTMC-b-PLA-b-PTMC-b-PLA polymerization (Table 1, entry 9). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:198:588. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). Figure S38. 1 H NMR spectrum (CDCl3, 300 MHz, 298 K) of PLA-b-PTMC-b-PLA polymerization (Table 1, entry 10). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:102:660. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). S24
25 Figure S39. 1 H NMR spectrum (CDCl3, 300 MHz, 298 K) of PLA-b-PTMC-b-PLA polymerization (Table 1, entry 11). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:312:510. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). Figure S40. 1 H NMR spectrum (CDCl3, 300 MHz, 298 K) of PLA-b-PTMC-b-PLA polymerization (Table 1, entry 12). Standard is hexamethylbenzene (HMB). [(fc P,B )Zn(μ-OCH2Ph)]2: HMB: TMC: LA ratio is 1:10:434:480. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 2.23 (s, 18H, CH3 HMB), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). S25
26 Figure S41. 1 H NMR spectrum (CDCl3, 300 MHz, 298 K) of L-LA melt polymerization. [(fc P,B )Zn(μ- OCH2Ph)]2: LA loading ratio is 1:600. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 5.16 (q, 2H, CHCH3 PLA). Figure S42. 1 H NMR spectrum (CDCl3, 300 MHz, 298 K) of PTMC-b-PLA melt polymerization. [(fc P,B )Zn(μ-OCH2Ph)]2:TMC:LA loading ratio is 1:600:600. δ (ppm) 1.58 (d, 6H, CHCH3 PLA), 2.05 (t, 2H, CH2 PTMC), 4.23 (t, 4H, CH2 PTMC), 5.16 (q, 2H, CHCH3 PLA). S26
27 Figure S C NMR spectrum (CDCl3, 126 MHz, 298 K) of the PLA-b-PTMC-b-PLA-b-PTMC-b-PLA copolymer (Table 1, entry 9). Figure S44. 1 H NMR spectra (CDCl3, 500 MHz, 298 K) corresponding to the stepwise preparation of PLA-b-PTMC-b-PLA-b-PTMC-b-PLA in the presence of HMB as an internal standard. S27
28 Conversion Studies Table S1. Molar mass versus conversion study of 1,3-trimethylene carbonate. Time (min) Conversion (%) M n (NMR) M n (SEC) Đ ,400 10, ,200 12, ,800 14, ,400 17, Conditions: benzene as a solvent (1.5 ml) and hexamethylbenzene as an internal standard. The experiment was performed at ambient temperature. Figure S45. Conversion of 1,3-trimethylene carbonate versus Mn. Table S2. Molar mass versus conversion study of L-lactide. Time (min) Conversion (%) M n (NMR) M n (SEC) Đ ,100 8, ,500 13, ,700 20, ,100 25, ,700 28, ,200 31, Conditions: benzene as a solvent (1.5 ml) and hexamethylbenzene as an internal standard. The experiment was performed at 70 C. S28
29 Figure S46. Conversion of L-lactide versus Mn. Figure S47. One pot polymerization of L-lactide (100 equivalents) and trimethylene carbonate (50 equivalents) in 0.5 ml of C6D6 at 50 C. S29
30 Size Exclusion Chromatography Figure S48. Polymerization of 101 equivalents of 1,3-trimethylene carbonate (Table 1, entry 2); Mn = 9,000; Mw =9,100; Đ = Figure S49. Polymerization of 283 equivalents of L-lactide (Table 1, entry 1); Mn = 39,800; Mw = 45,200; Đ = S30
31 Figure S50. SEC trace of PLA-b-PTMC copolymer (Table 1, entry 3); Mn = 55,500; Mw = 61,800; Đ = Figure S51. SEC trace of PTMC-b-PLA copolymer (Table 1, entry 4); Mn = 47,000; Mw = 75,000; Đ = S31
32 Figure S52. SEC trace of PTMC-b-PLA-b-PTMC copolymer (Table 1, entry 5); Mn = 43,200; Mw = 72,200; Đ = Figure S53. SEC trace of PLA-b-PTMC-b-PLA copolymer (Table 1, entry 6); Mn = 55,600; Mw = 81,400; Đ = S32
33 Figure S54. SEC trace of PLA-b-PTMC-b-PLA-b-PTMC copolymer (Table 1, entry 7); Mn = 48,200; Mw = 71,800; Đ = Figure S55. SEC trace of PTMC-b-PLA-b-PTMC-b-PLA-b-PTMC copolymer (Table 1, entry 8); Mn = 58,900; Mw = 87,900; Đ = S33
34 Figure S56. SEC trace of PLA-b-PTMC-b-PLA-b-PTMC-b-PLA copolymer (Table 1, entry 9); Mn = 53,200; Mw = 89,700; Đ = Figure S57. SEC trace of PLA-b-PTMC-b-PLA copolymer (Table 1, entry 10); Mn = 50,800; Mw = 65,800; Đ = S34
35 Figure S58. SEC trace of PLA-b-PTMC-b-PLA copolymer (Table 1, entry 11); Mn = 48,900; Mw = 69,400; Đ = Figure S59. SEC trace of PLA-b-PTMC-b-PLA copolymer (Table 1, entry 12); Mn = 51,200; Mw = 86,000; Đ = S35
36 Figure S60. SEC trace of PLA polymer obtained by melt polymerization; Mn = 25,800; Mw = 29,800; Đ = Figure S61. SEC trace of PTMC-b-PLA copolymer obtained by melt polymerization; Mn = 24,800; Mw = 29,000; Đ = S36
37 Differential Scanning Calorimetry Figure S62. DSC curve (third heating run) of a PLA sample (Mn (SEC) = 39,800; Table 1, entry 1). Figure S63. DSC curve (third heating run) of a PTMC sample (Mn (SEC) = 9,000; Table 1, entry 2). S37
38 Figure S64. DSC curve (third heating run) of a PLA-b-PTMC sample (Mn (SEC) = 55,500; Table 1, entry 3). Figure S65. DSC curve (third heating run) of a PTMC-b-PLA sample (Mn (SEC) = 47,000; Table 1, entry 4). S38
39 Figure S66. DSC curve (third heating run) of a PTMC-b-PLA-b-PTMC sample (Mn (SEC) = 43,200; Table 1, entry 5). Figure S67. DSC curve (third heating run) of a PLA-b-PTMC-b-PLA sample (Mn (SEC) = 55,600; Table 1, entry 6). S39
40 Figure S68. DSC curve (third heating run) of a PLA-b-PTMC-b-PLA-b-PTMC sample (Mn (SEC) = 48,200; Table 1, entry 7). Figure S69. DSC curve (third heating run) of a PTMC-b-PLA-b-PTMC-b-PLA-b-PTMC sample (Mn (SEC) = 58,900; Table 1, entry 8). S40
41 Figure S70. DSC curve (third heating run) of a PLA-b-PTMC-b-PLA-b-PTMC-b-PLA sample (Mn (SEC) = 53,200; Table 1, entry 9). Figure S71. DSC curve (third heating run) of a PLA-b-PTMC-b-PLA sample (Mn (SEC) = 50,800; Table 1, entry 10). S41
42 Figure S72. DSC curve (third heating run) of a PLA-b-PTMC-b-PLA sample (Mn (SEC) = 48,900; Table 1, entry 11). Figure S73. DSC curve (third heating run) of a PLA-b-PTMC-b-PLA sample (Mn (SEC) = 51,200; Table 1, entry 12). S42
43 Dynamic Mechanical Analysis Figure S74. Stress vs. strain curve of a PLA sample (Mn (SEC) = 39,800; Table 1, entry 2). Figure S75. Stress vs. strain curve of a PLA-b-PTMC sample (Mn (SEC) = 55,500; Table 1, entry 3) and PLA-b-PTMC sample (Mn (SEC) = 53,400). S43
44 Figure S76. Stress vs. strain curve of a PTMC-b-PLA sample (Mn (SEC) = 47,000; Table 1, entry 4) and PTMC-b-PLA sample (Mn (SEC) = 59,000). Figure S77. Stress vs. strain curve of a PTMC-b-PLA-b-PTMC sample (Mn (SEC) = 43,200; Table 1, entry 5). S44
45 Figure S78. Stress vs. strain curve of a PLA-b-PTMC-b-PLA sample (Mn (SEC) = 55,600; Table 1, entry 6). Figure S79. Stress vs. strain curve of a PTMC-b-PLA-b-PTMC-b-PLA sample (Mn (SEC) = 48,200; Table 1, entry 7). S45
46 Figure S80. Stress vs. strain curve of a PTMC-b-PLA-b-PTMC-b-PLA-b-PTMC sample (Mn (SEC) = 58,900; Table 1, entry 8). Figure S81. Stress vs. strain curve of a PLA-b-PTMC-b-PLA-b-PTMC-b-PLA sample (Mn (SEC) = 53,200; Table 1, entry 9). S46
47 Figure S82. Stress vs. strain curve of a PLA-b-PTMC-b-PLA sample (Mn (SEC) = 50,800; Table 1, entry 10). Figure S83. Stress vs. strain curve of a PLA-b-PTMC-b-PLA sample (Mn (SEC) = 48,900; Table 1, entry 11). S47
48 Figure S84. Stress vs. strain curve of a PLA-b-PTMC-b-PLA sample (Mn (SEC) = 51,200; Table 1, entry 12). S48
![X-ray Crystallographic Data Figure S85. Molecular structure drawing of [(fc P,B )Zn(μ-OCH2Ph)]2 with thermal ellipsoids at 50% probability; hydrogen atoms are omitted for clarity.](/docs-images/81/83888993/images/49-0.jpg "Selected distances (Å) and angles ( ): N(1)-Zn(1), 1.970(4); N(3)-Zn(1), 2.019(4); O(1)-Zn(1), 1.946(3), 1.981(4); N(1)-Zn(1)-N(3), 99.44(17); O(1)-Zn(1)-O(1) 80.26(16); N(3)-Zn(1)-O(1), 104.")
49 X-ray Crystallographic Data Figure S85. Molecular structure drawing of [(fc P,B )Zn(μ-OCH2Ph)]2 with thermal ellipsoids at 50% probability; hydrogen atoms are omitted for clarity. Selected distances (Å) and angles ( ): N(1)-Zn(1), 1.970(4); N(3)-Zn(1), 2.019(4); O(1)-Zn(1), 1.946(3), 1.981(4); N(1)-Zn(1)-N(3), 99.44(17); O(1)-Zn(1)-O(1) 80.26(16); N(3)-Zn(1)-O(1), (16), (17); N(1)-Zn(1)- O(1), (17), (16). Crystal data for C78H78B2Fe2N8O2P2Zn2; Mr = ; Monoclinic; space group P2/c; a = (4) Å; b = 9.378(2) Å; c = (8) Å; α = 90 ; β = (3) ; γ = 90 ; V = (17) Å 3 ; Z = 2; T = 100(2) K; λ = Å; μ = mm -1 ; dcalc = 1.261g cm -3 ; reflections collected; 9416 unique (Rint = ); giving R1 = , wr2 = for 7205 data with [I>2σ(I)] and R1 = , wr2 = for all 9416 data. Residual electron density (e Å -3 ) max/min: 1.873/ S49
50 DFT Calculations The full reference for the GAUSSIAN 09 2 program package can be found at the end of the document. G(kcal/mol) 36.0 Me Fe II 3.3 Me Me P Zn N N N B N H 2 OMe H B 0.0 L N B N N H N Zn MeO OMe Zn N N N N L = P Me Fe II Fe II H 3 P B Zn N N N N OMe L 1 Figure S86. Comparison between the energies of the dimeric zinc complex and two monomeric forms. S50
51 Figure S87. Comparison of the initiation steps of LA polymerization catalyzed by a monomeric (red) or dimeric (black) form of the zinc complex. S51
52 Figure S88. Comparison of the initiation steps of TMC polymerization catalyzed by a monomeric (red) or dimeric (black) form of the zinc complex. S52
53 Table S3. Energies, enthalpies, and free energies of the structures calculated at the PBE1PBE/SDD, G(d,p) (PCM, GD3, benzene)//b3lyp/lanl2dz, 6-31G(d) level. Structures correctio n of H correction of G G E with corrections new G with corrections lactide trimethylene carbonate TSI-II monomer -LA II monomer -LA TSII-III monomer -LA III monomer -LA TSI-II dimer -LA II dimer -LA TSII-III dimer -LA III dimer -LA TSI-II monomer TMC II monomer -TMC TSII-III monomer TMC III monomer -TMC TSI-II dimer -TMC II dimer -TMC TSII-III dimer -TMC III dimer -TMC Cat monomer propagation TSI-II monomer propagation-la II monomer propagation-la TSII-III monomer propagation-la III monomer - propagation-la S53
54 TSI-II monomer - propagation-tmc II monomer - propagation-tmc TSII-III monomer - propagation-tmc III monomer - propagation-tmc Cat dimer - propagation TSI-II dimer - propagation-la II dimer - propagation-la TSII-III dimer - propagation-la III dimer - propagation-la IV dimer - propagation-la TSI-II dimer - propagation-tmc II dimer - propagation-tmc TSII-III dimer - propagation-tmc III dimer - propagation-tmc IV dimer - propagation-tmc Cartesian coordinates for optimized structures lactide Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S54
55 trimethylene carbonate Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S55
56 1 Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S56
57 S57
58 Standard orientation: S58
59 Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S59
60 Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S60
61 TSI-II monomer -LA Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S61
62 S62
63 II monomer -LA Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S63
64 S64
65 TSII-III monomer -LA Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S65
66 III monomer -LA Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S66
67 S67
68 TSI-II dimer -LA Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S68
69 S69
70 II dimer -LA Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S70
71 S71
72 S72
73 TSII-III dimer -LA Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S73
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