Trans-stereospecific polymerization of butadiene and random copolymerization with styrene using borohydrido rare earths / magnesium dialkyl catalysts
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1 Trans-stereospecific polymerization of butadiene and random copolymerization with styrene using borohydrido rare earths / magnesium dialkyl catalysts A. Ventura a, T. Chenal b,c,d,e, *, M. Bria b,f, F. Bonnet b,c,d,e, P. Zinck b,c,d,e, Y. Ngono-Ravache a, E. Balanzat a, M. Visseaux b,c,d,e, * a CIMAP : Centre de Recherche sur les Ions, les Matériaux et la Photonique, CEA-CNRS, BP 5133, Cedex 5, France b Univ Lille Nord de France, F-5900 Lille, France c ENSCL, UCCS, CCM, F Villeneuve d Ascq, France d USTL, UCCS, CCM, F Villeneuve d Ascq, France e CNRS, UMR8181, F Villeneuve d Ascq, France f USTL, CCM RMN, F Villeneuve d Ascq, France SUPPLEMENTARY DATA Figure S1. 1 H NMR spectrum (300 MHz) of polybutadiene sample as synthesized in run 9. Details of peak attribution for 13 C NMR spectra of polybutadiene. MALDI ToF analysis of butadiene-styrene random copolymer. Figure S2: MALDI-ToF spectrum for butadiene-styrene copolymer isolated as described in the experimental section, rough data. Figure S3: spectrum enlargement (black line) and comparison to the simulation (red dots) with s = 0 and b = 12. Figure S4: discrimination between [s; b] and [s-1; b+2] neighboring peaks (4 g/mol shift). Figure S5. Intensity fit between rough data and simulated distributions having the Poisson statistics. Figure S6: Full spectra of simulated distributions having the Poisson statistics that fit with intensities of rough data peaks. Figure S7: Distribution of butadiene-styrene copolymers as determined by MALDI-ToF analysis
2 ppm Figure S1. 1 H NMR spectrum (300 MHz) of polybutadiene sample as synthesized in run 9. (CDCl 3 )
3 Details of peak attribution for 13 C NMR spectra of polybutadiene. Naming convention: in accordance with Makhiyanov [ref], each unit in the polymeric chains is denoted by an uppercase letter. Two lowercase letters describe the neighboring units. The left one refers to the preceding unit, which was bonded to the polymeric chain before the unit under study, in direction of the initiator. The right one refers to the next one, bonded after and towards the end of chain. The subscript number refers to the carbon number, the first one being linked to the preceding unit. T: trans-1,4-insertion of butadiene C: cis-1,4-insertion of butadiene V: vinyl by 1,2 insertion of butadiene B: butyl initiator E: ethyl initiator D: ethylidene i.e. =CH-CH 3 end-group A: allyl i.e. CH 2 -CH=CH 2 end-group Example: vt 1 c is the 1 rst carbon of a trans unit, inserted after a vinyl and followed by a cis unit. Regular trans sequence: tt 14 t tt 23 t Cis defect in trans chain: tc 14 t tc 23 t Vinyl unit or -1,2- defect in a trans chain: tv 3 t tv 4 t tt 2 v tt 3 v tt 4 v tv 1 t tv 2 t vt 1 t vt 2 t vt 3 t
4 Chain tip formed by butyl initiator: B 1 B 2 B 3 B 4 bt 1 t Chain tip formed by ethyl initiator: E 1 E 2 et 1 t Chain end formed by hydrolysis at the 4 th carbon trans-ethylidene: D 1 D 2 D 3 D 4 cis-ethylidene: D 3 * D 4 * Chain end formed by hydrolysis at the carbon number 2 Allyl-shaped end: A 1 A 2 A 3 A 4
5 Intens. [a.u.] MALDI ToF analysis of butadiene-styrene copolymers TC453_Dithranol_RP 0:M21 MS Raw Figure S2: MALDI-ToF spectrum for butadiene-styrene copolymer isolated as described in the experimental section, rough data. m/z Model compounds used for simulated spectra: butyl initiator s styrene units b butadiene units tag end-group ionization agent Molecular Formula: [C 31+8s+4b H 27+8s+6b ] +
6 Intensity (a. u.) Simulation Data m / z 1070 Figure S3: spectrum enlargement (black line) and comparison to the simulation (red dots) with s = 0 and b = 12. Coordinates of the above spectrum peaks, compared to molar masses and relative abundances of molecular formulas 12 C (79-i) 13 C i 1 H 99 : m/z [rel. intens.] 1 st peak (i = 0) 2 nd peak (i = 1) 3 rd peak (i = 2 ) 4 th peak (i = 3) Observed [100] [90] [32] [12] Calculated [100] [85] [36] [10] Figure S4: discrimination between [s; b] and [s-1; b+2] neighboring peaks (4 g/mol shift).
7 Figure S5. Intensity fit between rough data and simulated distributions having the Poisson statistics. Enlarged areas for selected numbers of styrene and butadiene, as representative examples.
8 Figure S6: Full spectra of simulated distributions having the Poisson statistics that fit with intensities of rough data peaks.
9 Intensity (a. u.) Data 17 Butadienes (continued) 0 Styrene 1 Styrene 2 Styrenes 3 Styrenes 4 Styrenes m / z Figure S7: Distribution of butadiene-styrene copolymers as determined by MALDI-ToF analysis
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