Supporting Information for. Synthesis of Ferrocene-Functionalized Monomers for Biodegradable. Polymer Formation
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1 Supporting Information for Synthesis of Ferrocene-Functionalized Monomers for Biodegradable Polymer Formation Brianna M. Upton, Raymond M. Gipson, Selma Duhović, Brian R. Lydon, Nicholas M. Matsumoto, Heather D. Maynard, and Paula L. Diaconescu* Department of Chemistry and Biochemistry, University of California, Los Angeles, California Table of Contents Experimental Procedures S2 NMR Spectra: 1 H and 13 C S4 Electrochemistry Data S18 Thermogravimetric Analysis S20 Computational Details S23 References S43 S1
2 Experimental Procedures 1-Bromoferrocene. Ferrocene (3.720 g, 20.0 mmol) and potassium tert-butoxide (1.615 g, 15.2 mmol) were weighed and added to a Schlenk flask along with 100 ml THF. The reaction was cooled to -78 o C and t-buli (25.0 ml, 40.0 mmol) was added dropwise over 30 minutes. The reaction was allowed to stir at -78 o C for 1 hour and then warmed to room temperature to stir for another hour. The reaction was cooled to -78 o C again and 1,1,2,2-tetrabromoethane (2.3 ml, 20.0 mmol) was added dropwise over 30 minutes. The reaction was allowed to stir at -78 o C for 1 hour and then warmed to room temperature to stir overnight. Volatiles were removed under reduced pressure and the residue was dissolved in dichloromethane. The organic phase was washed with water (2x50 ml), brine (2x50 ml), and dried over MgSO 4. The reaction was filtered and solvent was removed yielding a red-brown solid. The crude product contained ~10% of unreacted ferrocene and was used without further purification. Characterization was consistent with reported literature values. 1 Yield: g, 90.3% 1-Azidoferrocene (6). 1-bromoferrocene (4.783 g, 18.1 mmol) and CuCl (1.881 g, 19.0 mmol) were weighed and combined in 100 ml ethanol. Sodium azide (2.354 g, 36.2 mmol) was weighed, dissolved in water, and added dropwise to the reaction mixture. The reaction was shielded from light and allowed to stir at room temperature for 48 hours. After 48 hours, an additional 100 ml of water was added, the reaction was allowed to stir for 10 minutes, and the product was extracted into diethyl ether. The ether layer was dried over MgSO 4 and concentrated yielding an orange solid. Characterization was consistent with reported literature values. 1 Yield: g, 31.2% 1-Methylazidoferrocene (4). Ferrocene methanol (0.522 g, 2.4 mmol) and sodium azide (0.950 g, 14.6 mmol) were weighed and combined in glacial acetic acid (28 ml, 480 mmol). The reaction was heated to 50 o C under nitrogen for three hours. After three hours, the reaction was allowed to cool to room temperature and diluted with 200 ml dichloromethane. The reaction mixture was washed with saturated NaHCO 3 (3x100 ml) and water (1x100 ml). The organic layer was dried over MgSO 4, filtered and dried yielding a yellow solid. Characterization was consistent with reported literature values. 2 Yield: g, 88.7%. 1-Azidoethylferrocene (5). 1-hydroxyethylferrocene (1.018 g, 4.4 mmol) and sodium azide (1.730 g, 26.6 mmol) were weighed and combined in glacial acetic acid (50.6 ml, mmol). The reaction was heated to 50 o C under nitrogen for three hours. After three hours, the reaction was allowed to cool to room temperature and diluted with 200 ml dichloromethane. The reaction mixture was washed with saturated NaHCO 3 (3x100 ml) and water (1x100 ml). The organic layer was dried over MgSO 4, filtered and dried yielding a yellow-orange solid. Yield: g, 80.6% 1 H NMR (300 MHz, 25 o C, CDCl 3 ), δ (ppm): 4.38 (q, 1H, CH), 4.19 (m, 9 H, fc), 1.56 (d, 3H, CH 3 ). Dimethyl propargyl malonate. Dimethyl malonate (19.1 ml, mmol), potassium carbonate ( g, mmol), and propargyl bromide (5.001 g, 33.6 mmol) were combined in 200 ml acetone. The reaction mixture was heated to reflux for 24 h. After 24 h, the reaction was filtered and solvent was removed yielding a yellow oil. The crude product contained approximately 10% impurities and was used without further purification. Characterization was consistent with reported literature values. 3 Yield: g, 67.6%. 2-(Prop-2-yn-1-yl)propane-1,3-diol. Dimethyl propargyl malonate ( g, mmol) was weighed and added to a 1L Schlenk flask along with 400 ml diethyl ether. The reaction was cooled to 0 o C and lithium alumninum hydride (LAH) (9.423 g, mmol) was added portionwise. The reaction was heated to reflux for 24 hours. After 24 hours, an additional portion of LAH (4.717 g, mmol) was added and the reaction was heated to reflux for an additional 24 hours. The reaction was then cooled to 0 o C and quenched by the slow addition of Na 2 SO 4 10H 2 O until the reaction mixture becomes light grey in color. S2
3 The reaction mixture was filtered through a fritted filter yielding a yellow filtrate. The solid was washed with an additional portion of diethyl ether and the combined organic layers were dried over MgSO 4. The solution was filtered and solvent was removed yielding a yellow oil. The crude product was purified via flash gradient column chromatography (60% ethyl acetate to 100 % ethyl acetate in hexanes), yielding a colorless oil. Characterization was consistent with reported literature values. 4 Yield: g, 25.3%. S3
4 NMR Spectra 1 H spectrum of 1-azidoethylferrocene (5) S4
5 1 H spectrum of 5-(prop-2-yn-1-yl)-1,3-dioxan-2-one (1) 13 C spectrum of 5-(prop-2-yn-1-yl)-1,3-dioxan-2-one (1) S5
6 1 H spectrum of M 1 13 C spectrum of M 1 S6
7 1 H spectrum of M 2 13 C spectrum of M 2 S7
8 1 H spectrum of M 3 13 C spectrum of M 3 S8
9 1 H spectrum of M 4 13 C spectrum of M 4 S9
10 1 H spectrum of M 5 13 C spectrum of M 5 S10
11 1 H spectrum of M 6 13 C spectrum of M 6 S11
12 1 H spectrum of M 7 13 C spectrum of M 7 S12
13 1 H spectrum of M 8 13 C spectrum of M 8 S13
14 1 H spectrum of M 9 13 C spectrum of M 9 S14
15 1 H spectrum of pm 1 1 H spectrum of pm 2 S15
16 1 H spectrum of pm 3 1 H spectrum of pm 4 S16
17 1 H spectrum of pm 5 1 H spectrum of pm 6 S17
18 Electrochemistry Data Figure S1. Current as a function of scan rate for cyclic carbonate monomers and polymers. S18
19 Figure S2. Potential as a function of scan rate for cyclic carbonate monomers and polymers. S19
20 Thermogravimetric Analysis Figure S3: Thermogram for polymer pm1 Figure S4: Thermogram for polymer pm2 S20
21 Figure S5: Thermogram for polymer pm3 Figure S6: Thermogram for polymer pm4 S21
22 Figure S7: Thermogram for polymer pm5 Figure S8: Thermogram for polymer pm6 S22
23 Computational Details RCM = Ring closed monomer, ROM = Ring opened monomer All structures were optimized using the B3LYP density functional with the G* basis set in Gaussian 09. Vibrational frequency calculations confirmed structures were at minima by absence of imaginary frequencies. Frequency calculation results were also used to collect thermodynamic data for calculations on the change in Gibbs free energy of the ring opening reactions for each monomer. Table S1. Thermodynamic favorability for ring-opened products as determined by DFT calculations. Monomer ΔG (kcal/mol) M M M M M M M M M Optimized coordinates M1 RCM C C N C C N N H C C C Fe C C C C C H H H H H H H H C C C O C O C H H H O H H H H H C H H S23
24 M1 ROM Fe C C C C C C C C C C H H H H H H H H H N N C N H C C C C O H H O H H H H H C C H O O C C C C C C C H H H H H H H C H H M2 RCM C C N C C N N H C C C Fe C C C C C H H H H H H H H C C C O C O C H H H O H H H H H C H C H S2
25 H H M2 ROM Fe C C C C C C C C C C H H H H H H H H H N N C N H C C C C O H H O H H H H H C C H O O C C C C C C C H H H H H H H C H C H H H M3 RCM C C N C C N N H C C C Fe C C C C C H H H H H H H H C C C O C O C H H H S3
26 O H H H H H M3 ROM Fe C C C C C C C C C C H H H H H H H H H N N C N H C C C C O H H O H H H H H C C H O O C C C C C C C H H H H H H H M4 RCM C C N C C N N H C C C Fe C C C C C H H H H H H H H C C C O C O C H H O H H S4
27 H H H C H H C H H H O C O M4 ROM Fe C C C C C C C C C C H H H H H H H H H N N C N H C C C C O H H O H H H H C C H O O C C C C C C C H H H H H H H O C O C H H C H H H M5 RCM C C N C C N N H C C C Fe C C C C C H H H H S5
28 H H H H C C C O C O C H H O H H H H H C H O C O C H H H C H H H M5 ROM Fe C C C C C C C C C C H H H H H H H H H N N C N H C C C C O H H O H H H H C C H O O C C C C C C C H H H H H H H O C O C H C H H H C H H H S6
29 M6 RCM C C N C C N N H C C C Fe C C C C C H H H H H H H H C C C O C O C H H O H H H H H O C O C H H H M6 ROM Fe C C C C C C C C C C H H H H H H H H H N N C N H C C C C O H H O H H H H C C H O O C C C C C C C H H H H H H O C O S7
30 H C H H H M7 RCM C C C C C Fe H H H H H C C C C C H H H C H H N N H C C H C H H C H C O O C C C H H H H H N H M7 ROM C C C C C Fe C C C C C C N C C N N C C C C C O C O C C C C C C C O H H H H H H H H H H H H H H H H S8
31 H H H H H H H H H H H H H M8 RCM N N N C C C C C C C C Fe C C C C C C C C O C C C O H H H H H H H H C H H H H H H H H H H H H H H H M8 ROM C C C C C C C O C O C C C C O C C C N N N C C C C C C Fe C C C C C H H H H H S9
32 H H H C H H H H H H H H H H H H H H H H H H H H H H H M9 RCM C C C C C Fe C C C C C H H H H H H H H H N C C N N C H C H H C H O C C H H C H H H H O M9 ROM C C C C C Fe C C C C C N C C N N C C C O C C C O H C C C C C S10
33 C C O H H H H H H H H H H H H H H H H H H H H H H H H H H BnOH C C C C C C H H H H H C O H H H S11
34 References 1. Tennyson, A. G.; Khramov, D. M.; Varnado, C. D.; Creswell, P. T.; Kamplain, J. W.; Lynch, V. M.; Bielawski, C. W., Indirectly Connected Bis(N Heterocyclic Carbene) Bimetallic Complexes: Dependence of Metal Metal Electronic Coupling on Linker Geometry. Organometallics 2009, 28, (17), Ciampi, S.; Eggers, P. K.; Le Saux, G.; James, M.; Harper, J. B.; Gooding, J. J., Silicon (100) Electrodes Resistant to Oxidation in Aqueous Solutions: An Unexpected Benefit of Surface Acetylene Moieties. Langmuir 2009, 25, (4), Llerena, D.; Buisine, O.; Aubert, C.; Malacria, M., Synthesis of variously substituted allenediynes and their cobalt (I) mediated [2+2+2] cycloaddition reactions. Tetrahedron 1998, 54, (32), Trost, B. M.; Malhotra, S.; Mino, T.; Rajapaksa, N. S., Dinuclear Zinc Catalyzed Asymmetric Desymmetrization of Acyclic 2 Substituted 1,3 Propanediols: A Powerful Entry into Chiral Building Blocks. Chemistry A European Journal 2008, 14, (25), S2
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