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1 Supporting Information Polymerization-Induced Self-Assembly Using Visible Light Mediated Photoinduced Electron Transfer Reversible-Addition Fragmentation Chain Transfer Polymerization (PET-RAFT) Jonathan Yeow, Jiangtao Xu, and Cyrille Boyer* Centre for Advanced Macromolecular Design (CAMD) and Australian Centre for NanoMedicine (ACN), School of Chemical Engineering, UNSW Australia, Sydney, NSW 2052, Australia EXPERIMENTAL SECTION Materials Benzyl methacrylate (BzMA, Aldrich) was deinhibited by passing through a column of basic alumina. Oligo(ethylene glycol) methyl ether methacrylate (OEGMA) (M n = 300 g mol -1 ) (Sigma-Aldrich) was used as received. 2,2 -azobis(isobutyronitrile) (AIBN, Fluka, 98%) was purified by recrystallization from methanol. 4-Cyanopentanoic acid dithiobenzoate (CPADB) was prepared according to a procedure described elsewhere. 1 All the other reagents were used as received unless otherwise specified. S1
2 Instrumentation All 1 H-NMR spectra were recorded using a Bruker 300MHz spectrometer. All chemical shifts are reported in ppm (δ) relative to tetramethylsilane, referenced to the chemical shifts of residual solvent resonances. The molecular weight and dispersity of the prepared polymers were measured by GPC. The eluent was DMAc (containing 0.03% w/v LiBr and 0.05% w/v 2,6-dibutyl-4-methylphenol (BHT)) at 50 o C (flow rate of 1 ml/min) with a Shimadzu modular system comprising an SIL-10AD auto-injector, a Polymer Laboratories 5.0μm bead-size guard column (50 7.5mm 2 ) followed by four linear PL (Styragel) columns (10 5, 10 4, 10 3, and 500 Å) and an RID-10A differential refractive-index detector and a UV detector. DLS measurements were performed using a Malvern Zetasizer Nano Series running DTS software and using a 4 mw He Ne laser operating at a wavelength of 633 nm and an avalanche photodiode (APD) detector. The scattered light was detected at an angle of 173. UV-vis spectra were recorded using a CARY 300 spectrophotometer (Varian) equipped with a temperature controller. TEM studies of self-assembled block copolymers were conducted using a Transmission Electron Microscope (TEM, JEOL 1400) at an accelerating voltage of 100 kv. The polymerization dispersions were diluted with ethanol to give wt-% dispersions and deposited onto carbon coated copper grids (ProSciTech). Gels (and other dispersions) are first diluted with ethanol before depositing onto the TEM grid. Similar approaches are used in literature to image PISA-derived nanoparticles. 2,3 Uranyl acetate staining was applied to all samples. Synthesis of POEGMA macro-cta via RAFT polymerızatıon The synthesis of a POEGMA macro-cta by RAFT polymerization was performed as follows: OEGMA (12 g, mol), CPADB (0.224 g, mol), AIBN (16.4 mg, 0.1 mmol) and 50 ml MeCN were added to a 100 ml round bottom flask, sealed with a rubber septum and purged with nitrogen for 30 min at 0 o C. The polymerization was carried out for 5.5 h at 70 o C before quenching in an ice bath. The resulting polymer S2
3 was purified by precipitation in a diethyl ether and petroleum spirit (boiling range of o C) mixture (30:70, v/v). GPC analysis using DMAc as a mobile solvent and polystyrene standards indicated M n,gpc = g mol -1, Đ = The number average molecular weight was found to be g mol -1 by 1 H NMR of the purified polymer sample by comparing the RAFT agent aromatic protons at ppm (5H) to the methylene protons adjacent to ester bond at 4.1 ppm (DP n = 30). Synthesis of POEGMA-b-PBzMA block copolymers by PET-RAFT dispersion polymerization POEGMA-b-PBzMA copolymers were synthesized by PET-RAFT dispersion polymerization in ethanol. A typical experiment was set up as follows (with [BzMA]:[POEGMA] = 200:1, 100 ppm catalyst relative to monomer and total solids content of 10 wt%): POEGMA macro-cta (M n, NMR = g mol 1 and Đ = 1.10) (38.45 mg, mol), BzMA ( g, mol), Ru(bpy) 3 Cl. 2 6H 2 O (64 μg, mol, 64 ul of a 1 mg/ml EtOH stock solution) and ml EtOH (2.154 ml total solvent, 90 wt%) were added to a 4 ml glass vial, sealed with a rubber septum and purged with nitrogen for 20 min at 0 o C. The polymerization mixture was irradiated with blue LED light in a circular reactor (LED strip, λ max = 460 nm, 0.7 mw/cm 2 ) at room temperature for 24h before quenching by exposure to air (and storage in the dark). 1 H NMR (CDCl 3 ) of the crude polymerization mixture was used to measure the monomer conversion by comparing the relative intensities of the (P)BzMA methylene protons adjacent to the ester bond in the monomer (5.17 ppm) and polymer ( ppm) respectively. The number average molecular weight (M n, NMR) was found by comparing the same PBzMA peak ( ppm) with the POEGMA methylene protons at 4.1 ppm. GPC chromatograms were also used to determine the molecular weight (M n,gpc ) and dispersity. Note: In experiments involving the addition of MeCN as a co-solvent, the amount of MeCN to EtOH was calculated based on the relative volume fraction (v/v). Kinetic studies of the PET-RAFT PISA polymerization of BzMA by on-line Fourier transform nearinfrared (FTNIR) spectroscopy For FTNIR kinetic studies, a polymerization mixture of [BzMA]:[POEGMA] = 200:1, 100 ppm catalyst relative to monomer and total solids content of 20 wt% in 20:80 MeCN:EtOH was employed. Briefly, a S3
4 stock solution of POEGMA macro-cta (M n, NMR = g mol 1 and Đ = 1.10) (76.90 mg, mol), BzMA (0.301 g, mol), Ru(bpy) 3 Cl. 2 6H 2 O (128 μg, mol, 128 ul of a 1 mg/ml EtOH stock solution) and ml MeCN and ml EtOH (1.913 ml total solvent, 80 wt%, 20 v/v% MeCN) was prepared and a 800 μl aliquot added to a 900 μl FTNIR quartz cuvette (1 cm 2 mm). The cuvette was sealed with a rubber septum and purged with nitrogen for 20 min. The polymerization mixture was irradiated with blue LED light in a circular reactor (LED strip, λ max = 460 nm, 0.7 mw/cm 2 ) at room temperature. At predetermined time points (approximately every 3 hours) the cuvette was transferred from the light reactor to the sample holder manually for FTNIR measurement. The monomer conversions were calculated by the ratio of the integral of the wavenumber region cm-1 at different time points relative to the integral of the initial polymerization mixture (0% conversion). S4
5 ADDITIONAL FIGURES AND TABLE Figure S1. 1 H NMR spectra of a purified POEGMA macroraft agent used in this study (recorded in D 2 O). The number average molecular weight (M n, NMR ) was calculated from the following equation M n, NMR = ( I CH ppm /2)/( I Ar ppm /5) MW OEGMA where I Ar ppm and I CH ppm correspond to the intensities from the RAFT agent aromatic protons and the methylene protons adjacent to the POEGMA ester linkage respectively. S5
6 Table S1. Polymer characterization for the macro-cta used in this study. S6
7 Figure S2. Typical 1 H NMR spectra of (A) purified and (B) crude POEGMA-b-PBzMA diblock copolymers synthesized by PET-RAFT dispersion polymerization. Conversion of BzMA was determined using the following equation α = 100 I CH ppm / ( I CH ppm + I CH ppm ) where I CH ppm and ( I CH ppm correspond to the intensities from the methylene protons adjacent to the ester linkage in the BzMA polymer and monomer respectively. The number average molecular weight (M n, NMR ) of the POEGMA-b- PBzMA block copolymers was calculated from the following equation M n, NMR = DP POEGMA MW OEGMA + DP POEGMA MW BzMA [( I CH ppm )/( I CH ppm )] where DP POEGMA is the degree of polymerization of POEGMA macro-cta, MW OEGMA is the molecular weight of OEGMA, MW BzMA is the molecular weight of BzMA and I CH ppm and I CH ppm correspond to the intensities from the methylene protons adjacent to the PBzMA and POEGMA ester linkages respectively. S7
8 Figure S3. GPC traces of POEGMA-1 and POEGMA-b-PBzMA (Exp. i) recorded using dual RI (solid) and UV (λ = 305 nm, dotted) detectors. S8
9 Molecular weight (g/mol) Figure S4. Number distribution versus molecular weight for POEGMA-b-PBzMA (Exp. i).. To estimate the livingness according to GPC data, we first converted the molecular weight distributions to the corresponding number distributions. The y-axis values in the GPC distributions are proportional to nm 2, where n is the number of chains and M is the molecular weight. It follows that the number distribution, where the y-axis values are proportional to the number of chains, is given by w(log M)/M 2. Thus, if we plot w(log M)/M 2 vs M, the area under the curve between two given values of M is proportional to the number of chains within that range of M values. This calculation is estimated using the following hypothesis: the low molecular weight tails is attributed to dead polymers. S9
10 Figure S5. Model kinetic study performed using POEGMA-2 as a macro-cta, a [BzMA]:[POEGMA] = 200:1 and a 100 ppm catalyst relative to monomer demonstrating the evolution of (A) molecular weight and dispersity with monomer conversion and (B) GPC traces with monomer conversion. S10
11 Figure S6. Typical DLS intensity-average diameter distributions of POEGMA-b-PBzMA nanoparticles synthesised using (A) different catalyst concentrations (Exp. i, ii and iii) (B) different solids content (Exp. iv and v) and (C) different co-solvents (Exp. vii, viii and ix). S11
12 Figure S7. (A) TEM image of self-assembled POEGMA-b-PBzMA nanoparticles synthesized using an ON/OFF light stimulus (39 h total irradiation time). (B) Digital photo depicting the formation of a freestanding gel after 39 h total irradiation time. S12
13 Figure S8. Apparent absorbance (scattering) of visible light (λ = 400, 500 nm) with monomer conversion (determined by online FTNIR measurements) acquired during the RAFT dispersion polymerization of BzMA from a POEGMA macro-cta. ADDITIONAL REFERENCE: (1) Mitsukami, Y.; Donovan, M. S.; Lowe, A. B.; McCormick, C. L. Macromolecules 2001, 34, (2) Pei, Y.; Dharsana, N. C.; van Hensbergen, J. A.; Burford, R. P.; Roth, P. J.; Lowe, A. B. Soft Matter 2014, 10, (3) Jones, E. R.; Semsarilar, M.; Blanazs, A.; Armes, S. P. Macromolecules 2012, 45, S13
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