New Biomaterials from Renewable Resources - Amphiphilic Block Copolymers from δ-decalactone. Figure S4 DSC plot of Propargyl PDL...
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1 Eltron Supplmntry Mtrl (ESI) or Polymr Cmstry. Ts ournl s T Royl Soty o Cmstry 2015 Polymr Cmstry RSCPulsng Supportng Inormton Nw Bomtrls rom Rnwl Rsours - Amppl Blo Copolymrs rom δ-dlton Kulp K. Bnsl, Dp K, Lur Pur, Dr Irvn, Stvn M. Howl, Guspp Mntovn n Cmron Alxnr * TABLE OF CONTENT:- Lst o Fgurs Fgur S1 1 H NMR o ommrlly vll δ-lton qur n CDCl Fgur S2 1 H NMR sptr o proprgyl-pdl n BZD-PDL n CDCl Fgur S3 1 H NMR sptr o proprgyl PDL or n tr purton o polymr Fgur S4 DSC plot o Proprgyl PDL Fgur S5 13 C NMR o BZD-PDL n proprgyl-pdl n CDCl Fgur S6 SEC trs o (A) BZD-PDL n (B) proprgyl-pdl... 5 Fgur S7 Convrson o monomr wt tm or ROP o δ-lton usng mpeg s nttor n TBD (5 mol %) s t tlyst Fgur S8 1 H NMR sptrum n SEC tr o mpeg--pdl (urng nt stuy) tr 9 ontnng 5% o TBD s t tlyst Fgur S9 Ovrl FTIR sptr o mpeg, δ-lton monomr n mpeg--pdl opolymr Fgur S10 1 H NMR o mpeg--pdl n PDL--PEG--PDL opolymr n CDCl Fgur S11 13 C NMR o mpeg--pdl n PDL--PEG--PDL opolymr n CDCl Fgur S12 SEC trs o PEG mronttor n rnt lo opolymrs o lton n loroorm Fgur S13 DSC plots o (A) mpeg--pdl n (B) PDL--PEG--PDL, otn rom son tng/oolng yl Fgur S14 1 H NMR n 13 C NMR sptr o mpeg--pdl--ppdl n CDCl
2 Fgur S15 DSC plots o mpeg--pdl--ppdl rom son tng/oolng yl Fgur S16 SEC tr o mpeg--pcl otn usng loroorm s t mol ps Fgur S17 1 H NMR n 13 C NMR o mpeg--pcl n CDCl Fgur S18 CMC plot or (A) mpeg--pdl, (B) PDL--PEG--PDL, (C) mpeg--pdl--ppdl n (D) mpeg--pcl otn y t pyrn 1:3 p rto mto n wtr Fgur S19 Sz n Zt potntl o proprgyl-pdl nno mulson Fgur S20 Zt potntl vlus or (A) mpeg--pdl, (B) PDL--PEG--PDL, (C) mpeg--pcl n (D) mpeg--pdl-- PPDL mlls qur n HEPES 10 mm ur (ph 7.4) Fgur S21 UV-Vsl sorn sptr o Nl r (NR) n ton n mlls Fgur S22 Sz struton urv y ntnsty o (A) mpeg--pdl, (B) PDL--PEG--PDL n (C) mpeg--pdl--ppdl qur y DLS n wtr. (D) Apprn o mllr solutons n ontrol (ormulton wtout polymr) tr Nl r long Fgur S23 Pysl pprn o mllr suspnsons (otn v nnoprptton mto) n wtr (A) or n (B) tr ltrton troug 0.22 µm syrng ltr Fgur S24 Sz struton urvs y ntnsty o (A) Bln mpeg--pcl, (B) AmpB lo mpeg--pcl, n TEM mg o (C) Bln mpeg--pcl n (D) AmpB lo mpeg--pcl mlls. T mgs wr tn wtout stnng Fgur S25 SEC tr o mpeg--pdl tr 120 ys o storg t ph 7.4 (tmprtur 37 C) Lst o Tls Tl S1 Dt otn rom t nts nlyss o mpeg--pdl syntss
3 l g g,, l,g l Fgur S1 1 H NMR o ommrlly vll δ-lton qur n CDCl 3. Inst sowng nlrg rgon o sptrum twn 3.3 n 5.0 ppm. Pg 1
4 l, g g,,, g, g,,, l ,,,,,, l q r p s t o l m g g,,, g, g,,, q, r, s,,,,, p, t o l, m, q, r, s p, t o l, m, Fgur S2 1 H NMR sptr o proprgyl-pdl n BZD-PDL n CDCl 3. Inst sowng nlrg r o 1 HNMR to vsulston o gnost proton ps. Lttrng nt to postons on t ml struturs rr to protons lll on t NMR sptr Pg 2
5 Fgur S3 1 H NMR sptr o proprgyl PDL or n tr rton mxturs n ol mtnol. purton o o polymr y prptton o qun Ht Flow (W/g) C C(I) C Exo Up Tmprtur ( C) Unvrsl V3.9A TA Fgur S4. DSC plot o Proprgyl PDL. T prsnt tr ws qur romm t son tng/oolng yl. Pg 3
6 Fgur S5. 13 C NMR o BZD-PDL n proprgyl-pdl n CDCl 3. Pg 4
7 Fgur S6. SEC trs o (A) BZD-PDL n (B) pro ps. Avrg molulr wgts wr lult gnst prgyl-pdl, w wr qur usng loroorm s t mol polystyrn s t molr mss stnr. Pg 5
8 80 70 %C Convrson Tm (mn) Fgur S7. Convrson o monomr wt tm or ROPP o δ-lton usng mpeg s nttor n TBD (5 mol %) s t tlyst. Fgur S8. 1 H NMR sptrum n SEC tr t o mpeg--pdl (urng nt stuy) tr 9 ontnng 5% o TBD s t tlyst. SEC trs wr otn usng loroorm s t mol ps n polystyrn s molr mss stnr. For 1 H NMR nlyss t smpl ws ssolv n CDCl 3. Pg 6
9 Tl S1. Dt otn rom t nts nlyss o mpeg--pdl syntss. As sown n gur S8, ps 1 n 2 orrspon to opolymr n omopolymr rsptvly. (PD-Polysprsty Inx) Tm Convrson y NMR (%) M n, SEC P 1 (D) PD P1 M n, SEC P 2 (D) PD P 2 15 mn mn mpeg lton mpeg--pdl Trnsmttn Wvnumr m Fgur S9 Ovrl FTIR sptr o mpeg, δ-lton monomr n mpeg--pdl opolymr. Pg 7
10 l o p g, g,, l, o,, p l o p g, g,, l, o,, p Fgur S10. 1 H NMR o mpeg--pdl n PDL--PEG--PDL opolymr n CDCl 3 Pg 8
11 Pg 9 Fgur S C NMR o mpeg--pdl n PDL--PEG--PDL opolymr n CDCl 3. g g g
12 PEG4K mpeg5k PDL--PEG--PDL mpeg--pdl mpeg--pdl--ppdl Rtnton Tm (Mn.) Fgur S12. SEC trs o PEG mronttors n rnt lo opolymrs o lton, w wr otn usng loroorm s t mol ps. Polystyrn stnrs wr us to lrt t SEC. Pg 10
13 4 A 2 Ht Flow (W/g) C C C C(I) C C (I) C C 70.28J/g J/g C C Exo Up Tmprtur ( C) Unvrsl V3.9A TA In 4 B 2 Ht Flow (W/g) C C C C C(I) (I) (I) C C C 61.67J/g J/g C Exo Up Tmprtur ( C) Unvrsl V3.9A TA Fgur S13. DSC plots o (A) mpeg--pdl n (B) PDL--PEG--PDL, otn rom son tng/oolng yl. Pg 11
14 l o p q r s t u g, g,, s, t, l, o, q,,, r Fgur S14. 1 H NMR n 13 C NMR sptr o mpeg--pdl--ppdl n CDCl 3. u p Pg 12
15 4 2 Ht Flow (W/g) C C C (I) C(I) C C C 51.49J/g 51.49J/g C 50 C C 5.489J/g 5.489J/g C Exo Up Tmprtur ( C) Unvrsl V3.9A TA Fgur S15 DSC plots o mpeg--pdl--ppdl rom son tng/oolng yl. Fgur S16. SEC tr o mpeg--pcl otn usng loroorm s t mol ps. us to lrt t SEC. Polystyrn stnrs wr Pg 13
16 Pg 14 Fgur S17. 1 H NMR n 13 C NMR o mpeg--pcl n CDCl 3.,, g, g g g
17 Intnsty Rto (373/384) A B Polymr Conntrton µg/ml(log 10 Sl) Intnsty Rto (373/384) C D Polymr Conntrton µg/ml(log 10 Sl) Fgur S18. CMC plot or (A) mpeg--pdl, (B) PDL--PEG--PDL, (C) mpeg--pdl--ppdl n (D) mpeg--pcl otn y t pyrn 1:3 p rto mto n wtr. Pg 15
18 Fgur S19. Sz n Zt potntls o proprgyl-pdl nno mulson. Sz ws trmn n HPLC gr wtr wrs zt potntl ws msur n 10 mm HEPES ur. Fgur S20. Zt potntl msurmnts o (A) mpeg--pdl, (B) PDL--PEG--PDL,, (C) mpeg--pcl n (D) mpeg--pdl--ppdl mlls qur n HEPES 10 mm ur (ph 7.4). Pg 16
19 Asorn (normls) NR n ton Wvlngt (nm) NR n mlls 600 Mll smpls ontn Fgur S21. UV-Vsl sorn sptr o Nl r (NR) n ton n mlls. npsult NR n mpeg--pdl mlls sprs n wtr. Fgur S22. Sz struton urv y ntnsty o (A) mpeg--pdl, (B) PDL--PEG--PDL n (C) mpeg--pdl L-tr PPDL qur y DLS n wtr. (D) Apprn o mllr solutons n ontrol (ormulton wtout polymr) Nl r long. Pg 17
20 Fgur S23. Pysl pprn o mllr suspnson (otn v nnoprptton n (B) tr ltrton troug 0.22 µm syrng ltr. mto) n wtr (A) or Fgur S24. Sz struton urvs y ntnsty o (A) Bln mpeg--pcl, (B) AmpB lo mpeg--pcl, n TEM mg o (C) Bln mpeg--pcr 500 nm. n (D)( AmpB lo mpeg--pcl mlls. T mgs wr ror wtout stnng. Sl Pg 18
21 Fgur S25. SEC tr o m ws lrt usng polystyrn PEG--PDL tr 120 ys o storg t ph 7.4 (t stnrs n loroorm ws us s t mol m mprtur ps. 37 C). T SEC nstrumnt. Pg 19
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