Supporting Information. Competitive Interactions of π-π Junctions and their Role on Microphase Separation of Chiral Block Copolymers
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1 Supporting Information Competitive Interactions of π-π Junctions and their Role on Microphase Separation of Chiral Block Copolymers Tao Wen, Jing-Yu Lee, Ming-Chia Li, Jing-Cherng Tsai and Rong-Ming Ho *, Department of Chemical Engineering, National Tsing Hua University, Hsinchu 30013, Taiwan Department of Chemical Engineering, National Chung Cheng University, Chiayi 62102, Taiwan Department of Biological Science and Technology, National Chiao Tung University, Hsinchu, 30010, Taiwan 1
2 Materials. Unless otherwise noted, chemical reagents and solvents were purchased from Aldrich and used without further purification. PS-naphthalene-PLLA BCP*. PS-naphthalene-PLLA (SnL) was synthesized by sequential polymerization initiated by a double-headed initiator containing naphthalene-core (DHI) as shown in Scheme S1. Scheme S1. Synthetic routes of PS-naphthalene-PLLA (SnL). N-3-Hydroxypropyl-1,4,5,8-naphthalenetetracarboxylic-1,8-anhydride-4,5-imide (2). Substituted naphthalene monoimide was synthesized according to the method introduced by Ghadiri and co-workers. 1 1,4,5,8-Naphthalenetetracarboxylic acid dianhydride (compound 1, 2.0 g, 7.46 mmol) was weighed into a 100 ml flask. Water (50 ml) was added, followed by KOH (30 mmol). After dissolving the solid content, the solution was acidified to ph 6.4 using H 3 PO 4 (1M). Subsequently, 3-aminopropan-1-ol (0.741 ml, 7.46 mmol) was added, and the solution was again acidified to ph 6.4 using H 3 PO 4. The reaction vessel was fitted with a reflux condenser, and the mixture was heated to 110 C for 6 hours. The solution was slowly cooled to room temperature under stirring, and then filtered out the solid contents to acquire the remaining solution. Hydrochloric acid (1M) was added to the filtrate to 2
3 gain white solids from the solution. The solid was collected by filtration, and then washed with water, eventually dried under high vacuum to yield the desired product as off-white solids (compound 2, yield: 76 %). 1 H NMR (500 MHz, [D 6 ]DMSO) δ(ppm): 8.55 (d, J = 8 Hz, 2H), 8.18 (d, J = 8 Hz, 2H), 4.49 (s, 1H), 4.10 (t, J = 8 Hz, 2H), 3.50 (t, J = 6 Hz, 2H), 1.79(m, 2H). 13 C NMR (500 MHz, [D 6 ]DMSO) δ(ppm): 168.7, 162.8, 137.4, 134.2, 130.0, 129.2, 128.2, 124.6, 58.9, 37.8, HR-MS (ESI, positive): m/z [M+H] + = (calcd for C 17 H 12 NO 6 : ). Trifluoroacetic Acid Salt of 3-Aminopropyl 2-Bromoisobutyrate (3). Trifluoroacetic acid salt of 3-aminopropyl 2-bromoisobutyrate was synthesized based on the method reported by Li and co-workers. 2 First, the amino group of 3-aminopropan-1-ol was protected by t-boc. 3-aminopropan-1-ol (10 g, 0.13 mol) was reacted with Di-tert-butyl pyrocarbonate (29 g, 0.13 mol) in 100 ml DCM at room temperature for 6 hours. The solvent was evaporated out under vacuum to obtain light-yellow liquid (yield: approximately 100%). t-boc-aminopropyl alcohol (10 g, 57 mmol) in 100 ml DCM was cooled in an ice bath. 2-bromoisobutyryl bromide (13 g, 57 mmol) in 20 ml DCM was slowly added into the solution above. The reaction was slowly heated to room temperature, and then stirred for 6 hours. The crude product of t-boc-3-aminopropyl 2-bromoisobutyrate was obtained after removal of the solvent, and then purified by silica gel column. t-boc-aminopropyl 2-bromoisobutyrate (10 g, 31 mmol) was treated with 5 ml of trifluoroacetic acid (TFA) under vigorous stirring for removing the t-boc protection group. After the reaction, excess trifluoroacetic acid was removed, and the crude product was dried under a vacuum overnight. The crude product was purified by silica gel column (compound 3, yield: 90%). 1 H NMR (500 MHz, CDCl 3 ) δ(ppm): 8.00 (s, 3H), 4.23 (t, J = 6 Hz, 2H), 3.05 (t, J = 7 Hz), 2.06 (m, 2H), 1.88 (s, 6H). 13 C NMR (500 MHz, CDCl 3 ) δ(ppm): 172.2, (q), (q), 62.4, 55.6, 37.1, 30.4, 26.5, HR-MS (ESI, positive): m/z [M] + = (calcd for C 7 H 15 BrNO 2 : ). DHI. Compound 2 (1 g, 3 mmol) and compound 3 (1.03 g, 3 mmol) were dissolved in 5 ml DMSO at room temperature g potassium carbonate (K 2 CO 3 ) was added for 3
4 releasing the amino of compound 3 from the salt, and also accelerating the reaction. The reaction was kept at 40 C under vigorous stirring. After the reaction, the precipitate was filtered out, and then the reaction mixture was extracted sequentially using water. The organic phase was dried by magnesium sulfate. Solvent was removed by evaporation, and then the crude product was purified by silica gel column, eluting with ethyl acetate and petroleum ether (1/3, v/v). The final product (DHI) was pale yellow powder (Yield: 58%). 1 H NMR (500 MHz, [D 6 ]DMSO) δ(ppm): 8.64 (s, 4H), 4.50 (t, J = 5 Hz, 1H), 4.23 (t, J = 6 Hz, 2H), 4.18 (t, J = 7 Hz, 2H), 4.11 (t, J = 7 Hz, 2H), 3.51 (m, 2H), 2.05 (m, 2H), 1.87 (s, 6H), 1.81 (m, 2H); 13 C NMR (500 MHz, [D 6 ]DMSO) δ(ppm): 170.7, 162.6, 162.5, 130.3, 126.2, 126.0, 63.8, 62.5, 60.0, 57.2, 38.1, 37.2, 30.8, HR-MS (EI, positive): m/z [M] + = (calcd for C 24 H 23 BrN 2 O 7 : ). SnL. Polystyrene with terminal functional group (PS-naphthalene-OH) was synthesized by using the DHI, CuBr and 1,1,4,7,10,10-hexamethyl triethylenetetramine (HMTETA) as double-headed initiator, catalyst and ligand, respectively, for atom transfer radical polymerization (ATRP). Subsequently, SnL was synthesized by using the PS-naphthalene-OH as a macroinitiator for ring-opening polymerization (ROP) of L-lactide using tin(ii) 2-ethylhexanoate [Sn(Oct) 2 ] as catalyst. 1 H NMR (500 MHz, CDCl 3 ) δ(ppm): 8.72 (d, naphthalene), (m, 5H), 5.14 (q, J = 7 Hz, 1H), 1.81 (s, 1H), 1.56 (d, J = 7 Hz, 3H), 1.41 (s, 2H). Note the peak at around 8.71 ppm is attributed to the naphthalene junction. Also, BCPs* with poly(d-lactide) (PDLA) segment (PS-naphthalene-PDLA, SnD) was synthesized with D-lactide based on the same synthetic routes as for SnL. To acquire the total molecular weight and volume fraction of PLLA (f v PLLA ), the molecular weight of PS block was measured by GPC. Subsequently, the molecular weight of PLLA block and the f v PLLA were calculated based on 1 H NMR results (Table 1). Note that f v PLLA was calculated on the densities of PS at 1.04 and that PLLA at 1.25 g/cm 3. 4
5 DSC measurements Figure S1. DSC heating thermograms of PS-PLLA BCPs* with different junctions and different molecular weights after rapidly cooling from the molten state to room temperature at 150 o C/min. TEM micrographs and SAXS results Figure S2. TEM micrographs of self-assembled SaL45 under fast evaporation (a), moderate evaporation (b) and slow evaporation (c), and the corresponding 1D SAXS profiles (d). The rates of solvent evaporation are labelled. 5
6 CD and LD measurements Figure S3. The absorption spectra of SnL18 (a), SnL26 (b), and SnL40 (c) and SpL43 (d) in dilute chloroform solution (0.1 wt%). Figure S4. The CD spectra of SnL18 (a), SnL26 (b), and SnL40 (c) in dilute chloroform solution. The concentration is 2 mg/ml. 6
7 Figure S5. LD spectra of slow-cast films of SnL18 (a), SnL26 (b) and SnL40 (c). Table S1. Absorption intensity ratio (A 0-0 /A 0-1 ) of SnL18, SnL26, SnL40 and SpL43 films prepared by fast and slow evaporation SnL18 SnL26 SnL40 SpL43 A 0-0 /A 0-1 fast-cast slow-cast References: 1. Horne, W. S.; Ashkenasy, N.; Ghadiri, M. R. Modulating Charge Transfer through Cyclic D,L-α-Peptide Self-Assembly. Chem. Eur. J. 2005, 11, Yang, Z.; Zheng, S.; Harrison, W. J.; Harder, J.; Wen, X.; Gelovani, J. G.; Qiao, A.; Li, C. Long-Circulating Near-Infrared Fluorescence Core-Cross-Linked Polymeric Micelles: Synthesis, Characterization, and Dual Nuclear/Optical Imaging. Biomacromolecules 2007, 8,
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