Supporting Information for Macromolecules, DOI: Supramolecular Polylactides by the Cooperative Interaction of the End Groups and Stereocomplexation By M. Brzeziński*, T. Biela Table of Contents Figure S1: NMR spectrum of HO-PLA-AP Figure S2: NMR spectrum of HO-PLA-IC Figure S3: NMR spectrum of HO-PLA-U Figure S4. MALDI-TOF spectra of HO-PLA-AP Figure S5. MALDI-TOF spectra of HO-PLA-IC Figure S6. MALDI-TOF spectra of HO-PLA-U Figure S7: ATR FTIR spectra of enantiomeric UP-PLA-UPy and sc-upy-pla-upy Figure S8: DSC thermograms of UPy-PLA-OH and UPy-PLA-UPy Figure S9: SEM microphotographs sc-upy-pla-oh in 1,4-dioxane and chloroform Figure S10: SEM microphotographs sc-upy-pla-upy in N-methyl-2-pyrrolidinone Figure S11: DSC thermograms of sc-upy-pla-oh in different solvents Figure S12: DSC thermograms of sc-upy-pla-upy in different solvents Figure S13: SEM microphotographs sc-upy-pla-upy in 1,4-dioxane Figure S14: SEM microphotographs of UPy-PLA-OH and UPy-PLA-UPy Figure S15: SEM microphotographs sc-ho-pla-ic in (A) chloroform, (B) 1,4-dioxane and (C) N-methyl-2-pyrrolidinone. Figure S16: SEM microphotographs sc-ho-pla-u in (A) chloroform, (B) 1,4-dioxane and (C) N-methyl-2-pyrrolidinone.
Figure S1: NMR spectrum of HO-PLA-AP δ = 8.45 (br s, 1H, NH aminopyridine), 8.26 (d, 1H, CH=CH aminopyridine), 8.16 (d, 1H, CH=CH aminopyridine), 7.71 (t, 1H, CH=CH aminopyridine), 7.10 (t, 1H, CH=CH aminopyridine), 5.16 (q, 1H, CH-CH 3 polymer), 4.35 (q, 1H, CH-CH 3 end group polymer), 1.67 (d, 3H, CH 3 polymer) ppm. Figure S2: NMR spectrum of HO-PLA-IC δ = 5.98 (s, 1H, isocytosine-aryl), 5.16 (q, 1H, CH-CH 3 polymer), 4.35 (q, 1H, CH-CH 3 end group polymer), 2.19 (s, 3H, 6-methylisocytosine) 1.67 (d, 3H, CH 3 polymer) ppm.
Figure S3: NMR spectrum of HO-PLA-U δ = 8.25 (br s, 1H, NH uridine), 7.22 (d, 1H, CH=CH uridine), 5.72 (d, 1H, N-CH< sugar residue), 5.62 (d, 1H, CH=CH uridine), 5.16 (q, 1H, CH-CH 3 polymer), 5.03 (m, 2H, CH-CH sugar residue) 4.79 (q, 1H, sugrar residue), 4.38 (dd, 1H, sugar residue), 4.35 (q, 1H, CH-CH 3 end group polymer), 1.67 (d, 3H, CH 3 polymer) ppm. Figure S4. MALDI-TOF spectra of HO-PLA-AP with exact m/z values and the number of lactide units in the oligomers. The population with higher intensity ascribed to desired polymer chains: for n = 36, AP[O(O)CCH(CH 3 )] n OH, Na + (m/z = 2468.70), The second population of signals observed for macromolecules: for n = 35, AP[O(O)CCH(CH 3 )] n OH, Na + (m/z = 2396.50).
Figure S5. MALDI-TOF spectra of HO-PLA-IC with exact m/z values and the number of lactide units in the oligomers. The population with higher intensity ascribed to desired polymer chains: for n = 29, IC[O(O)CCH(CH 3 )] n OH, Li + (m/z = 3306.77), The second population of signals observed for macromolecules: for n = 44, IC[O(O)CCH(CH 3 )] n OH, Li + (m/z = 3234.58). Figure S6. MALDI-TOF spectra of HO-PLA-U with exact m/z values and the number of lactide units in the oligomers. The population with higher intensity ascribed to desired polymer chains: for n = 29, U[O(O)CCH(CH 3 )] n OH, Na + (m/z = 2468.70), The second population of signals observed for macromolecules: for n = 28, U[O(O)CCH(CH 3 )] n OH, Na + (m/z = 2396.50).
Figure S7: ATR FTIR spectra of enantiomeric UP-PLA-UPy and sc-upy-pla-upy Figure S8: DSC thermograms of UPy-PLA-OH (A) and UPy-PLA-UPy (B).
Figure S9: SEM microphotographs sc-upy-pla-oh precipitated from 1,4-dioxane(A) and after precipitation from chloroform to methanol (B) Figure S10: SEM microphotographs sc-upy-pla-upy in N-methyl-2-pyrrolidinone
Figure S11: DSC thermograms (I heating run) of sc-upy-pla-oh in different solvents (see legend on the figure). Figure S12: DSC thermograms of sc-upy-pla-upy in different solvents (see legend on the figure) Figure S13: SEM microphotographs sc-upy-pla-upy precipitated from 1,4-dioxane.
Figure S14: SEM microphotographs of UPy-PLA-OH (A, B) and UPy-PLA-UPy (C, D). Figure S15: SEM microphotographs sc-ho-pla-ic in (A) chloroform, (B) N-methyl-2- pyrrolidinone and (C) 1,4-dioxane.
Figure S16: SEM microphotographs sc-ho-pla-u in (A) chloroform, (B) 1,4-dioxane.