(Co)polymers by Iodine Transfer Polymerization Initiated
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1 Supporting Information Synthesis of ω-iodo and Telechelic Diiodo Vinylidene Fluoridebased (Co)polymers by Iodine Transfer Polymerization Initiated by an Innovative Persistent Radical Sanjib Banerjee,*,a Yogesh Patil, a Taizo Ono b and Bruno Ameduri*,a a Ingénierie et Architectures Macromoléculaires, Institut Charles Gerhardt, UMR 5253 CNRS, UM, ENSCM, Place Eugène Bataillon, Montpellier Cedex 5, France b National Institute of Advanced Industrial Science and Technology, , Anagahora, Shimoshidami, Moriyama, Nagoya, Aichi, , Japan S1
2 Materials. All reagents were used as received unless described otherwise. 1,1- Difluoroethylene (vinylidene fluoride, VDF) and 1,1,1,3,3-pentafluorobutane (HFC-245 fa, Solkane 365mfc) were kindly supplied by Solvay S.A. (Tavaux, France and Brussels, Belgium). Tert-butyl 2-trifluoromethacrylate and trifluoroiodomethane (CF 3 I) were kindly offered by Tosoh F-Tech Company (Shunan, Japan). Acetonitrile was purchased from Fisher Scientific and distilled over calcium hydride. Dimethyl carbonate was purchased from Sigma- Aldrich and degassed before use. IC 4 F 8 I was a gift from Dupont Performance Elastomers. Deuterated acetone used for NMR spectroscopy was purchased from Euroiso-top (Grenoble, France) (purity>99.8%). Characterization. Size Exclusion Chromatography (SEC) Measurements. Molar masses (M n s) and dispersities (Ðs) of the (co)polymers were obtained from size exclusion chromatography (SEC) with a triple-detection GPC from Agilent Technologies using a PL LC light scattering detector with two diffusion angles (15 and 90 ), a PL capillary viscometer, and a 390-LC PL refractive index detector and two PL ResiPore mm columns. DMF (containing 0.1 wt% of LiCl) was used as the eluent at a flow rate of 0.8 ml min 1 and toluene as the flow rate marker. The entire SEC-HPLC system was thermostated at 35 C. PMMA standards were used for calibration. Aliquots were sampled from the reaction medium, diluted with DMF (containing 0.1 wt% of LiCl), filtered through a 20 mm PTFE Chromafil Membrane (pore size 0.2 µm) and finally analyzed by SEC under the conditions described above. Typical sample concentration was 10 mg ml -1. The results were processed using the corresponding Cirrus software. Nuclear Magnetic Resonance (NMR) Spectroscopy. The compositions of the copolymers and their microstructures were determined by 1 H and 19 F NMR spectroscopies. 1 H and 19 F NMR spectra were recorded on a Bruker AC 400 Spectrometer (400 MHz for 1 H and 376 S2
3 MHz for 19 F) using deuterated chloroform or acetone, as the solvent and tetramethylsilane (TMS) (or CFCl 3 ) as the references for 1 H (or 19 F) nuclei. Coupling constants and chemical shifts are given in Hertz (Hz) and parts per million (ppm), respectively. The experimental conditions for recording 1 H [or 19 F] NMR spectra were as follows: flip angle 90 [or 30 ], acquisition time 4.5 s [or 0.7 s], pulse delay 2 s [or 5 s], number of scans 32 [or 64], and a pulse width of 5 µs for 19 F NMR. Thermogravimetric Analysis (TGA). The purified and dried polymer samples were subjected to thermogravimetric analysis under air using a TGA 51 apparatus from TA Instruments at a heating rate of 10 C min 1 from room temperature to 580 C. The sample size varied between 10 and 15 mg. Differential Scanning Calorimetry (DSC). DSC analyses were performed using a Netzsch DSC 200 F3 instrument under N 2 atmosphere. The instrument was calibrated with noble metals and checked before analysis with an indium sample (T m = 156 C). The heating or cooling range was from -60 C to 200 C at a scanning rate of 10 C min 1. Melting transitions were determined at the maximum of the enthalpy peaks and its area determined the melting enthalpy ( H m ). S3
4 Table S1. Reaction Conditions and Results for the ITP of VDF Initiated by PPFR in the presence of CF 3 I in Dimethyl Carbonate at 80 o C. a time (h) convn b c M n,sec (g/mol) Đ c -CH 2 CF 2 I d (%) entry Acronyms: VDF: vinylidene fluoride; PPFR: perfluoro-3-ethyl-2,4-dimethyl-3-pentyl; a Reaction conditions: Volume of solvent = 60 ml. [VDF] 0 :[ CF 3 I] 0 :[PPFR] 0 = 50:1:0.1 b VDF conversion assessed by 19 F NMR spectroscopy using eqn (1). c determined by SEC in DMF (containing 0.1 wt% LiCl), system was calibrated using poly(methyl methacrylate) standards. d Assessed by 19 F NMR spectroscopy using eqn (7). e Assessed by 19 F NMR spectroscopy using eqn (8). -CF 2 CH 2 I e (%) Table S2. Structural Assignments of 19 F NMR Resonances of I-poly(VDF-co-MAF- TBE)-I (Figure 9). The Chemical Shift Values (in ppm) Correspond to Structures in Red Italics. signal structure δ (ppm) c -CH 2 CF 2 -I -39 d -CH 2 C(CF 3 )(COO t Bu) -69 e - CH 2 CF 2 -CH 2 C(CF 3 )(COO t Bu)-CH 2 CF 2 -CH 2 CF a -CF 2 -[CH 2 -CF 2 ] n -CH 2 - HT b (-CF 2 of VDF in the alternating VDF MAF-TBE dyad -95 c CH 2 CF 2 -CF 2 CH 2 -I -109 p {CH 2 -CF 2 (CF 2 ) 2 CF 2 )-CH 2 } c 1 CH 2 CF 2 -CH 2 CF 2 -CF 2 CH 2 -CH 2 CF 2 -CH 2 CF a 1 CH 2 CF 2 -CH 2 CF 2 -CF 2 CH 2 -CH 2 CF 2 -CH 2 CF p -CF 2 (CF 2 ) 2 CF S4
5 Scheme S1. Degradation of tert-butyl ester groups of the poly(vdf-co-maf-tbe) copolymers upon heating under air above 150 o C. S5
6 Figure S1. 1 H NMR spectrum of CF 3 -PVDF-CF 3 homopolymer prepared by free radical polymerization of VDF initiated by PPFR at 80 C (P1, Table 1), recorded in acetone-d 6 at 20 C. S6
7 Figure S2. 19 F NMR spectrum of CF 3 -PVDF-CF 3 homopolymer prepared by free radical polymerization of VDF initiated by PPFR at 80 C (P1, Table 1), recorded in acetone-d 6 at 20 C. For CF 3 -PVDF- CF 3 homopolymers: /6 /2 M n,nmr = (2 M CF3 ) + {M VDF (DP n of VDF)} 1 (S2) where M CF3 and M VDF stand for 69 and 64 g mol -1, respectively. S7
8 Figure S3. 1 H NMR spectrum of I-PVDF-I copolymer prepared by ITP of VDF initiated by PPFR in the presence of IC 4 F 8 I as the chain transfer agent at 80 C (P9, Table 1), recorded in acetone-d 6 at 20 C. (*) Solvent (acetone) peak. S8
9 t = 16 h t = 5 h t = 4 h t = 3 h t = 2 h t = 1 h δ F (ppm) Figure S4. Time evolution of the 19 F NMR spectra (acetone-d 6, 20 C) during the ITP of VDF initiated by PPFR in the presence of CF 3 I as the CTA ([VDF] 0 :[CF 3 I] 0 :[PPFR] 0 = 50:1:0.1) at 80 C. S9
10 * δ H (ppm) Figure S5. 1 H NMR spectrum of CF 3 -poly(vdf-co-maf-tbe)-i copolymer prepared by ITP of VDF with MAF-TBE initiated by PPFR in the presence of CF 3 I as the chain transfer agent at 80 C (P11, Table 1), recorded in acetone-d 6 at 20 C. (*) Solvent (acetone) peak. S10
11 Figure S6. 19 F NMR spectrum of CF 3 -poly(vdf-co-maf-tbe)-i copolymer prepared by ITP of VDF with MAF-TBE initiated by PPFR in the presence of CF 3 I as the chain transfer agent at 80 C (P11, Table 1), recorded in acetone-d 6 at 20 C. S11
12 Figure S7. TGA thermograms of PVDF(-I) prepared by PPFR initiated free radical polymerization (P1, Table 1, solid red line), ITP in the presence of CF 3 I as the CTA (P2-P8 and P10, Table 1) and ITP in the presence of IC 4 F 8 I as the CTA (P9, Table 1), heated at 10 C min 1 under air. Figure S8. TGA thermograms of (bis)iodinated poly(vdf-co-maf-tbe) copolymers synthesized under the same experimental conditions using different CTAs: CF 3 I (solid line) and IC 4 F 8 I (dotted line), (P11 and P12, Table 1), heated at 10 C min 1 under air. S12
13 Figure S9. DSC thermogram of CF 3 -PVDF- CF 3 homopolymer (P1, Table 1). Figure S10. DSC thermogram of CF 3 -PVDF-I homopolymer (P2, Table 1). S13
14 Figure S11. DSC thermogram of CF 3 -PVDF-I homopolymer (P3, Table 1). Figure S12. DSC thermogram of CF 3 -PVDF-I homopolymer (P4, Table 1). S14
15 Figure S13. DSC thermogram of CF 3 -PVDF-I homopolymer (P5, Table 1). Figure S14. DSC thermogram of CF 3 -PVDF-I homopolymer (P6, Table 1). S15
16 Figure S15. DSC thermogram of CF 3 -PVDF-I homopolymer (P7, Table 1). Figure S16. DSC thermogram of CF 3 -PVDF-I homopolymer (P8, Table 1). S16
17 Figure S17. DSC thermogram of I-PVDF-I homopolymer (P9, Table 1). Figure S18. DSC thermogram of I-PVDF-I homopolymer (P10, Table 1). S17
18 Figure S19. DSC thermogram of CF 3 -poly(vdf-co-maf-tbe)-i homopolymer (P11, Table 1). Figure S20. DSC thermogram of I-poly(VDF-co-MAF-TBE)-I homopolymer (P12, Table 1). S18
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