4-cyanopentanoic acid dithiobenzoate (CPADB) was synthesized as reported by Y.

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1 Eletroni upplementry Mteril (EI) for Journl of Mterils Chemistry B This journl is The Royl oiety of Chemistry 2012 ynthesis of 4-ynopentnoi id dithioenzote (CPADB). 4-ynopentnoi id dithioenzote (CPADB) ws synthesized s reported y Y. Mitsukmi et l (Mitsukmi, Donovn et l. 2001). Briefly, the dithioenzoi id (DTBA) ws firstly prepred using sodium methoxide (30 % solution in methnol, 45 g, 250 mmol), elementl sulphur (8.0 g, 250 mmol), nhydrous methnol (62.5 g) nd enzyl hloride (15.75 g, 125 mmol). The retion mixture ws heted in n oil th t 67 ºC for 10 h. After this time, the retion mixture ws ooled to 7 ºC using n ie th. The preipitted slt ws removed y filtrtion nd the solvent removed in vuum. The residue ws dissolved in deionized wter (125 ml). The rude sodium dithioenzote solution ws idified with 1.0 N HCl (125 ml) nd extrted with diethyl ether (50 ml). Deionized wter (75 ml) nd 1.0 N NH (150 ml) were dded, nd sodium dithioenzote ws trnsfered to the queous phse. The sodium dithioenzote solution (87.5 ml) nd potssium ferriinide (III) (8.23 g, 25 mmol) were mixed in deionized wter (150 ml) under vigorous stirring. The red preipitte ws filtered nd wshed with deionized wter until the wshings eme olourless. The solid ws filtered nd dried in vuum t room temperture overnight. The produt, di(thioenzoyl) disulphide, ws rerystllized from ethnol. Finlly, the synthesis of 4-ynopentnoi id dithioenzote (CPADB) ws rried out y dissolving 4,4 -zois(4-ynopentnoi id) (2.92 g, 11.5 mmol) nd di(thioenzoyl)disulfide (2.13 g, 7 mmol) in 40 ml of distilled ethyl ette. The retion solution ws heted t reflux for 18h nd ethyl ette ws removed in vuum. The rude produt ws isolted y olumn hromtogrphy (siligel 60 Å, mesh) using ethyl ette hexne (2:3) s eluent. Frtions tht were red in olour were omined nd dried over nhydrous sodium sulphte overnight. The solvent mixture ws removed in vuum, nd the red oily residue pled in freezer t -20 ºC,

2 Eletroni upplementry Mteril (EI) for Journl of Mterils Chemistry B This journl is The Royl oiety of Chemistry 2012 whereupon it rystllized. The trget ompound ws rerystllized with n ette:hexne (2:3) mixture (melting point 98 ºC, mesured in Perkin Elmer DC7 pprtus from 20 to 180 ºC t onstnt rte of 10 ºC/min. Yield ws 78%). Melting point otined ws in good onordne with the vlue desried in iliogrphy (Thng, Chong et l. 1999). The 1 H-NMR spetr of this regent is shown in figure 1, where the resonne signls t ppm orresponds to the romti protons designed s,,, d nd e in the hemil struture, the signls t ppm represent the methylene protons (g,h) from the ynopentnoi id frgment nd the signls t 2 ppm orrespond to the protons from the methyl group in the sme frgment (f). N C d e f g h H f,e,d g h ppm Figure 1. CPADB RAFT gent 1 H-NMR spetr hrteristion.

3 Eletroni upplementry Mteril (EI) for Journl of Mterils Chemistry B This journl is The Royl oiety of Chemistry 2012 ynthesis of PMMA mroraft gent. The synthesis of PMMA mroraft gent (P1) ws rried out using CPADB s RAFT gent (Fig. 2). The theoretil moleulr weight n then e lulted using Mn = [M]/[RAFT]*M Monomer *+M Rft where [M] nd [RAFT] re the initil onentrtions of the monomer nd the RAFT gent, respetively, nd is the onversion. The polymeriztion of seond monomer, [2-(methryloyloxy)ethyl] trimethylmmonium, in the presene of poly(methylmethrylte) mroraft gent leds to hin extension nd therefore to the formtion of mphiphili lok opolymers PMMA--PMAETMA (Fig. 3). CPADB did not introdue ny deresing of the polymeriztion rte of MMA. Conversion of MMA ws lulted grvimetrilly nd orroorted y 1 H-NMR, otining the sme vlue with oth tehniques. It ws oserved liner inrese of onversion with time, showing good ontrol of the polymeriztion. After 24h, 97% onversion of PMMA ws otined with M n = 55000, PDI = 1.24 (figure 4). CPADB, AIBN 60 ºC, 24h in ulk 970 H MMA CH 3 P1 Figure 2. MMA polymeriztion sheme using CPADB RAFT gent to otin the P1.

4 Eletroni upplementry Mteril (EI) for Journl of Mterils Chemistry B This journl is The Royl oiety of Chemistry 2012 H C 2 Me 970 P1 V501, DM 70 ºC, 6 h H n m C 2 Me N N PMMAn--PMAETMAm MAETMA Figure 3. MAETMA polymeriztion sheme using P1. PMMA ulk onversion MMA onversion retion time (h) Figure 4. Kineti plot of MMA mro-raft gent polymeriztion. GPC elution urves (Fig. 5) lerly showed pek shift to higher moleulr weights with inresing polymeriztion time. The urves were ll unimodl with no sign of oexisting low nd high moleulr weight speies tht my e yielded from unontrolled polymeriztion. The inrese in Mn with onversion (Fig. 5) ws liner nd the resulting polydispersity ws nrrow (Mw/Mn = 1.24).

5 Eletroni upplementry Mteril (EI) for Journl of Mterils Chemistry B This journl is The Royl oiety of Chemistry 2012 PMMAmroRAFT_24h PMMAmroRAFT_20h PMMAmroRAFT_8h PMMAmroRAFT_5h PMMAmroRAFT_2h time (min) Figure 5. Moleulr weight evolution of P1 gent with time nd onversion. 1 H-NMR spetrum of P1 without previous purifition is shown in figure 6 with the hrteristi ssignement of signls. Resonne signls tht orrespond to the protons from MMA residul monomer: δ ppm (CH 2 ) nd δ 3.75 ppm (CH 3 ) re lso indited. d e f H 1, ,1 e,f ppm Figure 6. PMMA mroraft gent 1 H-NMR spetrum fter 24h of ulk polymeristion.

6 Eletroni upplementry Mteril (EI) for Journl of Mterils Chemistry B This journl is The Royl oiety of Chemistry 2012 Fourier trnsform infrred spetrosopy fitted with ttenuted totl refletne (ATR- FTIR) ATR-FTIR spetr were reorded on Perkin-Elmer-petrum ne spetrophotometer. Infrred (IR) spetr were otined etween 4000 nd 400 m -1 y 32 sns nd with snning resolution of 4m -1. FTIR hrteriztion of NP systems. The FTIR spetr (Fig. 7) of nnoprtile systems hrged with emiprin showed two different ronyl group signs, the first one t 1650m -1 elongs to emiprin nd the seond one t 1750m -1 or 1720m -1 elong to PLGA or the ioni polymers respetively. Besides, t 3500m -1 the nnoprtile systems showed wide nd similr to emiprin spetr, tht elongs to the H groups of emiprin m m m -1 Figure 7. FTIR spetr of emiprin, PLGA nd nnoprtile system of PLGA hrged with emiprin.

7 Eletroni upplementry Mteril (EI) for Journl of Mterils Chemistry B This journl is The Royl oiety of Chemistry 2012 Referenes Mitsukmi, Y., M.. Donovn, et l. (2001). "Wter-olule Polymers. 81. Diret ynthesis of Hydrophili tyreni-bsed Homopolymers nd Blok Copolymers in Aqueous olution vi RAFT." Mromoleules 34(7): Thng,. H., Y. K. Chong, et l. (1999). "A novel synthesis of funtionl dithioesters, dithiormtes, xnthtes nd trithiorontes." Tetrhedron Letters 40(12):

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