Supporting information. Aluminum complexes based on pyridine substituted alcohols: synthesis, structure, catalytic application in ROP
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Supporting information Aluminum complexes based on pyridine substituted alcohols: synthesis, structure, catalytic application in ROP Marina M. Kireenko, a Ekaterina A. Kuchuk, a Kirill V. Zaitsev, a, * Viktor A. Tafeenko, a Yuri F. Oprunenko, a Andrei V. Churakov, b Elmira Kh. Lermontova, b Galina S. Zaitseva a and Sergey S. Karlov a a Chemistry Department, Moscow State University, B-234 Leninskie Gory, Moscow, Russia b Institute of General and Inorganic Chemistry, Russian Acad. Sci., Leninskii pr., 31, Moscow, Russia zaitsev@org.chem.msu.ru Table of Contents Fig. S1 1 H NMR spectrum for 3a (CDCl 3, rt) Fig. S2 1 H NMR spectrum for 3a (CDCl % DMSO-d6, rt) Fig. S3 DOSY NMR spectrum for 3a and calculation of M w Fig. S4 Molecular structure of complex 2c Fig. S5. MALDI-TOF mass spectrum of a PLA sample prepared with 2a Fig. S6. 1 H NMR spectra (CDCl 3 ) for BnO-PLLA, prepared with 2a (75 % conversion) Fig. S7. 1 H NMR spectra (CDCl 3 ) for MeO-PLLA, prepared with 2c (100 % conversion) Fig. S8.Homodecoupled 1 H NMRspectra (CDCl 3 ) for BnO-PLLA Fig. S9. ln([la] 0 /[LA]) versus time plot for L-lactide polymerization with 2a-4a Fig. S10. M n versus conversion plot for L-lactide polymerization with 3a S3 S3 S4 S6 S6 S7 S8 S8 S9 S9 S1
2 Fig. S11. Ln([M] 0 /[M]) vs. time plots for the polymerization of L-lactide in the presence of catalytic complex 4a S10 Fig. S12. 1 H NMR spectrum (CDCl 3, rt) for PLLA (the sample contains the polymer, [(3)(PLLA)], with ligand fragment) Figure S13. 1 H NMR spectrum (CDCl 3, rt) of complex 2a Figure S C NMR spectrum (CDCl 3, rt) of complex 2a Figure S15. 1 H NMR spectrum (CDCl 3, rt) of complex 3a Figure S C NMR spectrum (CDCl 3, rt) of complex 3a Figure S17. 1 H NMR spectrum (CDCl 3, rt) of complex 4a Figure S C NMR spectrum (CDCl 3, rt) of complex 4a Figure S C NMR spectrum (CDCl 3, rt) of complex 3b Figure S C NMR spectrum (CDCl 3, rt) of complex 3b Figure S21. 1 H NMR spectrum (CDCl 3, rt) of complex 4b Figure S C NMR spectrum (CDCl 3, rt) of complex 4b Figure S23. 1 H NMR spectrum (CDCl 3, rt) of complex 2c Figure S C NMR spectrum (CDCl 3, rt) of complex 2c Figure S25. 1 H NMR spectrum (CDCl 3, rt) of complex 3c Figure S C NMR spectrum (CDCl 3, rt) of complex 3c Figure S27. 1 H NMR spectrum (CDCl 3, rt) of complex 4c Figure S28. 1 H NMR spectrum (C 6 D 6, rt) of complex 2d Figure S C NMR spectrum (C 6 D 6, rt) of complex 2d S10 S11 S11 S12 S12 S13 S13 S14 S14 S15 S15 S16 S16 S17 S17 S18 S18 S19 S2
3 1-H_001001r toluene Fig. S1 1 H NMR spectrum for 3a (CDCl 3, rt). 3-H_001001r 3-H_001001r toluene Fig. S2 1 H NMR spectrum for 3a (CDCl % DMSO-d6, rt). S3
4 Fig. S3 DOSY NMR spectrum for 3a (600 MHz, DMSO-d6, room temperature; the admixture of toluene is present). The formula of MW calculation [Angew. Chem., Int. Ed. 2013, 52, ] 3 1 k BT ( ) D= 2 1, where 3MW N eff A 3 MW S MW MW S molecular weight of the solvent MW molecular weight of the solute S4
5 eff - the effective density of a small molecule -viscosity N A - the Avogadro number k B - Boltzmann constant D diffusion coefficient T - temperature Using known calculation algorithm the molecular weights of two particles was established: M 1 = 820 g/mol, D= 1.74*10-10 m 2 /s (M 1 (theor)= 774.9), what corresponds to dimeric (3a) 2 ; M 2 = g/mol, D=2.19*10-10 m 2 /s (M 1 (theor)= 465.6), what corresponds to adduct of monomer with DMSO. S5
6 Fig. S4 Molecular structure of complex 2c. Hydrogen atoms are omitted for clarity. Intens. [a.u.] \sample 2 in HABA\1SRef m/z Fig. S5. MALDI-TOF mass spectrum of a PLA sample prepared with 2a (Table 2, entry 1) (solvent THF, HABA matrix, 2,5-dihydroxybenzoic acid). S6
7 H Chloroform-d O c CH 3 b O O b CH 3 c O b O n L-LA a c Fig. S6. 1 H NMR spectra (CDCl 3 ) for BnO-PLLA, prepared with 2a (75 % conversion). S7
8 a CH 3 O c H O b CH 3 O O b O CH 3 a a b c 0.04 Chloroform-d Fig. S7. 1 H NMR spectra (CDCl 3 ) for MeO-PLLA, prepared with 2c (100 % conversion) Fig. S8.Homodecoupled 1 H NMRspectra (CDCl 3 ) for BnO-PLLA. S8
9 Fig. S9. ln([la] 0 /[LA]) versus time plot for L-lactide polymerization with 2a-4a. Fig. S10. M n versus conversion plot for L-lactide polymerization with 3a. S9
10 Fig. S11. Ln([M] 0 /[M]) vs. time plots for the polymerization of L-lactide in the presence of catalytic complex 4a (100:1:1) at 80 C; [LA]/[initiator]= 100. MeO-PLLA 1H 3C 200 к 1 загрузка отбор пробы через 4 часа.esp (3)(PLLA) MeO-PLLA MeO-PLLA (3)(PLLA) Fig. S12. 1 H NMR spectrum (CDCl 3, rt) for PLLA (the sample contains the polymer, [(3)(PLLA)], with ligand fragment). S10
11 2a_1H.esp 2a_1H.esp a_1H.esp Figure S13. 1 H NMR spectrum (CDCl 3, rt) of complex 2a. 2a_13C.esp a_13C.esp a_13C.esp Figure S C NMR spectrum (CDCl 3, rt) of complex 2a. S11
12 3A 1H.ESP 3A 1H.ESP Chloroform-d A 1H.ESP Chloroform-d Figure S15. 1 H NMR spectrum (CDCl 3, rt) of complex 3a. 3a 13C.esp a 13C.esp Figure S C NMR spectrum (CDCl 3, rt) of complex 3a. S12
13 4a 1H.esp 4a 1H.esp a 1H.esp Figure S17. 1 H NMR spectrum (CDCl 3, rt) of complex 4a. 4a 13C.esp 4a 13C.esp a 13C.esp Figure S C NMR spectrum (CDCl 3, rt) of complex 4a. S13
14 301_PY(CH2CME2O)(CH2CPH2O)ALCL_CH_H+++.ESP 301_PY(CH2CME2O)(CH2CPH2O)ALCL_CH_H+++.ESP _PY(CH2CME2O)(CH2CPH2O)ALCL_CH_H+++.ESP Figure S C NMR spectrum (CDCl 3, rt) of complex 3b. 301_PY(CH2CME2O)(CH2CPH2O)ALCL_CH_C+++.ESP 301_PY(CH2CME2O)(CH2CPH2O)ALCL_CH_C+++.ESP _PY(CH2CME2O)(CH2CPH2O)ALCL_CH_C+++.ESP Figure S C NMR spectrum (CDCl 3, rt) of complex 3b. S14
15 mk322h_001001r 3.95 mk322h_001001r Figure S21. 1 H NMR spectrum (CDCl 3, rt) of complex 4b. mk322c-new_001001r mk322c-new_001001r Figure S C NMR spectrum (CDCl 3, rt) of complex 4b. S15
16 2c 1H.esp 2c 1H.esp c 1H.esp Figure S23. 1 H NMR spectrum (CDCl 3, rt) of complex 2c. 2c 13C.esp c 13C.esp c 13C.esp Figure S C NMR spectrum (CDCl 3, rt) of complex 2c. S16
17 3c 1H.esp c 1H.esp Figure S25. 1 H NMR spectrum (CDCl 3, rt) of complex 3c. 3c_C13_.esp 3c_C13_.esp c_C13_.esp c_C13_.esp Figure S C NMR spectrum (CDCl 3, rt) of complex 3c. S17
18 4c 1H.esp 4c 1H.esp c 1H.esp Figure S27. 1 H NMR spectrum (CDCl 3, rt) of complex 4c. 2d 1H.esp BENZENE-d6 2d 1H.esp BENZENE-d Figure S28. 1 H NMR spectrum (C 6 D 6, rt) of complex 2d. S18
19 2d 13C.esp BENZENE-d6 2d 13C.esp BENZENE-d Figure S C NMR spectrum (C 6 D 6, rt) of complex 2d. S19
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