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1 Supporting Information Towards Singlet Oxygen Delivery at a Measured Rate: A Selfreporting Photosensitizer Sundus Erbas-Cakmak #, Engin U. Akkaya # * # UNAM-National Nanotechnology Research Center, Bilkent University, Ankara, Turkey, TR Department of Chemistry, Bilkent University, Ankara, Turkey, TR eua@fen.bilkent.edu.tr S1
2 Contents 1. General...S2 2. Singlet Oxygen Generation Experiments...S2 3. Additional Figures...S3 4. Synthesis...S5 5. References...S13 6. MMR Spectra...S14 7. High Resolution Mass Spectra...S25 1. General All chemicals and solvents purchased from Sigma-Aldrich were used without further purification. Spectra of 1 H NMR and 13 C NMR were recorded using a Bruker DPX-400 in CDCl 3 with TMS as internal reference. Splitting in the spectra are shown as s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), dd (doublet of doublet), and br (broad). Absorption spectrometry was performed using a Varian spectrophotometer. Steady state fluorescence measurements were conducted using a Varian Eclipse spectrofluorometer. Column chromatography of all products was performed using Merck Silica Gel 60 (particle size: mm, mesh ASTM). Reactions were monitored by thin layer chromatography using fluorescent coated aluminum sheets. Solvents used for spectroscopy experiments were spectrophotometric grade. Mass spectra were recorded on Agilent Technologies 6530 Accurate-Mass Q-TOF LC/MS. FRET efficiency was determined using time-resolved approach with the formula below: E = 1- F (DA)/ F (D) where F (D) and F( DA) refer to fluorescence quantum yields donor (D) alone and donor as a part of EET system respectively. Both measurements were performed in acetonitrile. 2. Singlet Oxygen Generation Experiments Measurements were performed using 660 nm LED and samples were irradiated with the light source from a 2 cm distance. All samples were aerated for 5 min prior to experiments. After S2
3 incubation under dark for 30 min, light was irradiated for 60 min and UV-Vis spectra were recorded at each 10 min intervals. 4 M BOD1 and 2.5 M BOD2 was used for the experiments. Prior to each experiment, solvent is saturated with oxygen by bubbling air through the solutions for 5 min. 3. Additional Figures Figure S1. Excitation spectra of BOD 1and A1 in acetonitrile. Fluorescence is collected from 670 nm. Figure S2. Excitation spectra of BOD 2and A2 in acetonitrile. Fluorescence is collected from 684 nm. S3
4 Figure S3. Change in absorbance spectra of BOD 1 after 60 min irradiation of red light in acetonitrile. Figure S4. Change in absorbance spectra of BOD 2 after 60 min irradiation of red light in acetonitrile. S4
5 4. Synthesis Synthesis of Compound 3: 4-hydroxybenzaldehyde (1.23 g, 10 mmol) and compound 1 1 (4.8 g, 15 mmol) were dissolved in 50 ml acetonitrile. K 2 CO 3 (3.2 g, 22.4 mmol) and a few crystals of benzo-18-crown-6 were added. The reaction was refluxed until all 4- hydroxybenzaldehyde was consumed. The solvent was evaporated in vacuo, extracted with water and CH 2 Cl 2. Organic layer was dried with Na 2 SO 4 and evaporated under reduced pressure. The product was purified by silica gel column chromatography using CH 2 Cl 2 /Hexane (75:25, v/v). Fraction containing compound 3 was collected then the solvent was removed under reduced pressure (2.1 g, 7.8 mmol, 78%). 1 H NMR (CDCl 3, 400 MHz, ppm) 9.80 (s, 1H), 7.75 (d, J=7.42 Hz, 2H, ArH), 6.94 (d, J=7.81 Hz, 2H, ArH), 4.13 (m, 2H; OCH 2 ), 3.80 (m, 2H; OCH 2 ), (m, 8H; OCH 2 ), 3.27 (s, 3H, OCH 3 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 190.8, 163.9, 131.9, 130.1, 114.9, 71.9, 70.9, 70.7, 70.6, 69.5, 67.8, Synthesis of Donor Compound, D: CH 2 Cl 2 (300 ml) was purged with Ar for 30 min. 4-(prop- 2-ynyloxy) benzaldehyde 2 (1 g, 6.24 mmol) and 2,4-dimethyl-3-ethyl pyrrole (1.54 g, 1.70 ml, 12.6 mmol) were added. 3 drops of trifluoroacetic acid was added. The reaction mixture was stirred at room temperature for 12h. Then, tetrachloro-1,4-benzoquinone (1.54 g, 6.24 mmol) was added and the reaction mixture was stirred at room temperature for 45 min. Then S5
6 triethyl amine (8 ml) and boron trifluoride diethyl etherate (8 ml) were added sequencially. After stirring at room temperature for 30 min, it was extracted with water. Organic layer was dried with Na 2 SO 4 and evaporated under reduced pressure. The product was purified by silica gel column chromatography using CHCl 3 /Hexane (75:25, v/v) as mobile phase. Fraction containing D was collected then the solvent was removed under reduced pressure (400 mg, 0.92 mmol, 15%). 1 H NMR (CDCl 3, 400 MHz, ppm) 7.21 (d, J = 8.72 Hz, 2H; ArH), 7.10 (d, J = 8.72 Hz, 2H; ArH), 4.78 (d, J = Hz, 2H; OCH 2 ), 2.57 (t, J = 2.44 Hz, 1H; CH), 2.55 (s, 6H; ArCH 3 ), 2.32 (q, J = 7.56 Hz, 4H; ArCH 2 ), 1.33 (s, 6H; ArCH 3 ), 1.0 (t, J = 7.60 Hz, 6H; CH 3 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 158.0, 153.6, 140.0, 138.4, 132.8, 131.1, 129.8, 128.9, 115.6, 78.1, 75.8, 56.0, 17.1, 14.6, 12.5, Synthesis of Acceptor Compound A 1 : Compound 3 (112 mg, 0.42 mmol) and compound D (70 mg, 0.17 mmol) were dissolved in benzene (40 ml). Piperidine (0.40 ml) and acetic acid (0.40 ml) were added. The reaction mixture was refluxed using Dean Stark apparatus until all BODIPY was consumed. After the reaction was completed, it was extracted with CH 2 Cl 2 and water. Organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. The product was purified by silica gel column chromatography using EtOAc/MeOH (98:2, v/v). Fraction containing compound A 1 was collected then the solvent was removed under reduced pressure (90 mg, 0.10 mmol, 59%). S6
7 1 H NMR (CDCl 3, 400 MHz, ppm) 7.68 (d, 2H, J = Hz; ArH), 7.59 (d, 4H, J = 8.72 Hz; ArCH 3 ), (d + d, 2H + 2H; ArH), 7.13 (d, 2H, J = 8.64 Hz; ArH), 6.97 (d, 4H, J =8.72 Hz; ArH), 4.80 (d, 2H, J = 2.32 Hz; OCH 2 ), 4.20 (t, 4H, J =4.68 Hz; OCH 2 ), (m, 8H; OCH 2 ), 3.60 (m, 4H; OCH 2 ), 3.40 (s, 6H; OCH 3 ), 2.61 (q, 4H, J = 7.36 Hz; ArCH 2 ), 1.40 (s, 6H; ArCH 3 ), 1.15 (t, 6H, J = 7.40 Hz; CH 3 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 159.4, 158.0, 150.4, 138.7, 137.7, 135.3, 133.6, 133.3, 129.9, 129.2, 128.7, 118.2, 115.6, 114.9, 78.1, 75.9, 72.0, 70.9, 70.7, 70.6, 69.7, 67.6, 59.0, 56.1, 18.4, 14.1, HRMS (TOF-ESI): m/z calcd for C 54 H 65 BF 2 N 2 NaO [M+Na] + ; found: [M+Na]+, Δ = 9.0 ppm. Synthesis of Compound 6 3 : Argon was purged in EtOH (10 ml) for 15 min. NaOH (0.88 g, 22 mmol) and 3-mercaptopropanol (2 g, 1.86 ml, 22 mmol) were added and the reaction was stirred at 0 o C ice bath for 30 min while the flask was sealed. Then, cis-1,2-dichloroethylene (1.04 g, 0.8 ml, 11 mmol) in degassed EtOH (1 ml) was added and the reaction mixture was refluxed for 18 h. After cooling to RT, it was extracted with petroleum ether and brine. Organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. The product was purified by silica gel column chromatography using EtOAc/Hexanes (50:50, v/v) as mobile phase. Fraction containing compound 6 was collected then the solvent was removed under reduced pressure (2 g, 9.60 mmol, 87%). 1 H NMR (CDCl 3, 400 MHz, ppm) 6.12 (s, 2H), 3.73 (t, J = 6.08 Hz, 4H; OCH 2 ), 2.84 (t, j = 7.04 Hz, 4H; SCH 2 ), 2.57 (b, 2H; OH), 1.88 (m, 4H; CH 2 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 123.9, 60.9, 32.7, HRMS (TOF-ESI): m/z calcd for C 8 H 16 NaO 2 S 2 + : [M+Na] + ; found: [M+Na] +, Δ = 17.0 ppm. S7
8 Synthesis of Compound 7: (Z)-3,3'-(ethene-1,2-diylbis(sulfanediyl))dipropan-1-ol, compound 6 (1.7 g, 8.16 mmol) was dissolved in 30 ml CH 2 Cl 2 and 3.40 ml Et 3 N. In a dropper, p-toluene sulfonyl chloride (3.11 g, mmol) was dissolved in CH 2 Cl 2 10 ml and was added to the previous solution dropwise while the reaction mixture was being cooled with ice bath. It was stirred for 12h. After the extraction with water, organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. The product was purified by silica gel column chromatography using CHCl 3 as mobile phase. Fraction containing compound 7 was collected, then the solvent was removed under reduced pressure (white solid, 5.70 mmol, 2.95 g, 70%). 1 H NMR (CDCl 3, 400 MHz, ppm) 7.80 (d, 4H, J = 8.48 Hz; ArH), 7.37 (d, 4H, J = 8.48 Hz; ArH), 5.98 (s, 2H; ArH), 4.14 (t, 4H, J = 5.93 Hz; OCH 2 ), 2.73 (t, 4H, J = 7.00 Hz; SCH 2 ), 2.48 (s, 6H, ArCH 3 ), 1.95 (m, 4H; CH 2 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 144.9, 132.9, 129.9, 127.9, 123.9, 68.3, 29.9, 29.6, HRMS (TOF-ESI): m/z calcd for C 22 H 28 NaO 6 S [M+Na] +, found: [M+Na] +, Δ = 10.0 ppm. Synthesis of Compound 8: Compound 7 (200 mg, 0.38 mmol) was dissolved in 10 ml DMSO and sodium azide (247 mg, 3.80 mmol) was added to the reaction mixture. It was stirred 2h at 60 o C. After cooling to RT, it was extracted with EtOAc and brine. Organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. (yellow oil, 3.80 mmol, 98 mg quantitative). 1 H NMR (CDCl 3, 400 MHz, ppm) 6.10 (s, 2H), 3.45 (t, J = 6.57 Hz, 4H; NCH 2 ), 2.81 (t, j = 6.96 Hz, 4H; SCH 2 ), 1.89 (m, 4H; CH 2 ). S8
9 13 C NMR (CDCl 3, 400 MHz, ppm) 124.0, 49.6, 31.1, Synthesis of Compound 18: Compound D (80 mg, 184 mol) and compound 8 (476 mg, 1.84 mmol) were dissolved in CH 2 Cl 2 (6 ml) and MeOH (3 ml). Flask was covered with aluminium folio to avoid light and Ar was purged for 15 min. Saturated solutions of CuSO 4.5H 2 O (100 l) and sodium ascorbate (100 l) were added. Catalytic amount of Cu (0) was added. The reaction mixture was stirred for 12 h at room temperature. After the reaction was completed, it was extracted with CH 2 Cl 2 and water. Organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. The product was purified by silica gel column chromatography using EtOAc/Hexanes (50/50; v/v) as mobile phase. Fraction containing compound 9 was collected, then the solvent was removed under reduced pressure (94 mol, 65 mg, 51%). 1 H NMR (CDCl 3, 400 MHz, ppm) 7.71 (s, 1H; ArH), 7.20 (d, J = 8.72 Hz, 2H; ArH), 7.12 (d, J = 8.56 Hz, 2H; ArH), 6.15 (d, J = 8.32 Hz, 1H; CH), 6.06 (d, J = 8.37 Hz, 1H; CH), 5.26 (s, 2H, OCH 2 ), 4.55 (t, J = 6.76 Hz, 2H; NCH 2 ), 3.46 (t, J = 6.53 Hz, 2H; NCH 2 ), 2.84 (t, J = 6.97 Hz, 2H; SCH 2 ), 2.75 (t, J = 6.76 Hz, 2H; SCH 2 ), 2.53 (s, 6H; ArCH 3 ), 2.30 (m, 2H + 4H; CH 2 + ArCH 2 ), 1.82 (m, 2H; CH 2 ), 1.33 (s, 6H; ArCH 3 ), 1.0 (t, J = 7.49 Hz, 6H; CH 3 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 158.7, 153.6, 143.7, 140.0, 138.4, 132.7, 131.1, 129.6, 128.5, 127.0, 125.4, 123.2, 122.7, 115.3, 62.1, 49.6, 48.4, 31.1, 30.7, 30.2, 29.4, 17.1, 14.6, 12.5, HRMS (TOF-ESI): m/z calcd for C 34 H 43 BF 2 N 8 NaOS [M+Na] +, Δ = 8.89 ppm [M+Na] +, found: S9
10 Synthesis of Gate 2: Compound 9 (30 mg, 43 mol) and compound A 1 (35 mg, 37 mol) were dissolved in CH 2 Cl 2 (6 ml) and MeOH (3 ml). Flask was covered with aluminium folio to avoid light and Ar was purged for 15 min. Saturated solutions of CuSO 4.5H 2 O (100 l) and sodium ascorbate (100 l) were added. Catalytic amount of Cu (0) was added. The reaction mixture was stirred for 12 h at room temperature. After the reaction was completed, it was extracted with CH 2 Cl 2 and water. Organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. The product was purified by silica gel column chromatography using EtOAc/MeOH (90/10; v/v) as mobile phase. Fraction containing BOD 1 was collected, then the solvent was removed under reduced pressure (25 mol, 40 mg, 68%). 1 H NMR (CDCl 3, 400 MHz, ppm) (s+ s+ d, 1H + 1H + 2H; ArH), 7.58 (d, J = 8.80 Hz, 4H; ArH), (d + d + d, 2H + 2H + 2H; ArH), (d + d, 2H + 2H; ArH), 6.96 (d, J = 8.76 Hz, 2H; ArH), 6.11 (s, 2H; CH), 5.29 (s, 2H; OCH 2 ), 5.27 (s, 2H; OCH 2 ), 4.55 (m, 2H + 2H; NCH 2 ), 4.20 (t, J = 5.0 Hz, 4H, OCH 2 ), 3.90 (m, 4H; OCH 2 ), 3.78 (m, 4H; OCH 2 ), (m, 8H; OCH 2 ), 3.59 (m, 4H; OCH 2 ), 3.40 (s, 6H; OCH 3 ), 2.77 (m, 4H, SCH 2 ), 2.61 (m, 4H; CH 2 ), 2.53 (s, 6H; ArCH 3 ), 2.30 (m, 4H + 4H; ArCH 2 ), 1.38 (s, 6H; ArCH 3 ), 1.34 (s, 6H; ArCH 3 ), 1.17 (t, J = 7.36 Hz, 6H; CH 3 ), 1.00 (t, J = 7.60 Hz, 6H; CH 3 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 159.4, 158.7, 153.6, 150.4, 143.8, 140.0, 138.7, 138.4, 137.7, 135.4, 133.6, 133.2, 132.7, 130.5, 130.0, 129.6, 128.9, 128.7, 128.6, 124.1, 124.0, 123.2, 118.1, 115.6, 115.3, 114.9, 71.9, 70.9, 70.7, 70.6, 69.7, 67.6, 62.0, 59.0, 48.4, 30.7, 30.3, 17.1, 14.6, 14.0, 12.5, 11.9, S10
11 HRMS (TOF-ESI): m/z calcd for C 88 H 108 B 2 F 4 N 10 NaO 10 S [M+Na] +, Δ = 6.2 ppm [M+Na] +, found: Synthesis of Compound 11: Compound 10 4 (150 mg, 0.40 mmol) and N-bromosuccinimide (178 mg, 1.0 mmol) were dissolved in CH 2 Cl 2 (3 ml) and dimethylformamide (1 ml). The reaction mixture was stirred for 30 min at room temperature. After the reaction was completed, it was extracted with CH 2 Cl 2 and water. Organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. (0.37 mmol, 200 mg, 93%). 1 H NMR (CDCl 3, 400 MHz, ppm) 7.18 (d, J = 8.36 Hz, 2H; ArH), 7.14 (d, J = 8.36 Hz, 2H; ArH), 4.80 (d, J = 2.44 Hz, 2H; OCH 2 ), 2.62 (s, 6H; ArCH 3 ), 1.45 (s, 6H; ArCH 3 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 158.5, 153.9, 142.0, 140.6, 130.7, 129.1, 127.3, 116.0, 111.8, 77.9, 76.1, 56.1, 13.9, HRMS (TOF-ESI): m/z calcd for C 22 H 20 BBr 2 F 2 N 2 O [M+H] +, found: [M+H] +, Δ = 5.6 ppm. S11
12 Synthesis of Acceptor Compound A 2 : Compound 11 (100 mg, 0.19 mmol) and compound 3 (120 mg, 0.45 mmol) were dissolved in benzene (40 ml). Piperidine (0.30 ml) and acetic acid (0.3 ml) were added. The reaction mixture was refluxed using Dean Stark apparatus until all BODIPY was consumed. After the reaction was completed, it was extracted with CH 2 Cl 2 and water. Organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. The product was purified by silica gel column chromatography using EtOAc/MeOH (85:15, v/v). Fraction containing compound A 2 was collected then the solvent was removed under reduced pressure (60 mg, 0.06 mmol, 31%). 1 H NMR (CDCl 3, 400 MHz, ppm) 8.13 (d, 2H, J = Hz; ArH), 7.64 (d + d, 2H + 2H; ArH), 7.22 (d, 2H, J = 8.48 Hz; ArH), 7.16 (d, 2H, J = 8.53 Hz; ArH), 7.00 (d, 2H, J = 8.60 Hz; ArH), 4.80 (d, 2H, J = 2.08 Hz; OCH 2 ), 4.21 (t, 4H, J = 4.48 Hz; OCH 2 ), 3.92 (t, 4H, J = 4.48 Hz; OCH 2 ), (m, 12H; OCH 2 ), 3.60 (t, 4H, J = 4.24 Hz; OCH 2 ), 3.41 (s, 6H; OCH 3 ), 2.60 (s, 1H; CH), 1.30 (s, 6H; ArCH 3 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 160.2, 158.5, 148.4, 141.0, 138.8, 138.5, 132.3, 129.9, 129.7, 129.3, 127.9, 116.2, 115.9, 115.0, 110.1, 77.9, 76.1, 72.0, 70.9, 70.7, 70.6, 69.7, 67.6, 59.1, 56.1, 26.7, Synthesis of BOD 2: Compound 9 (30 mg, 43 mol) and compound A 2 (46 mg, 44 mol) were dissolved in CH 2 Cl 2 (6 ml) and MeOH (3 ml). Flask was covered with aluminium folio to avoid light and Ar was purged for 15 min. Saturated solutions of CuSO 4.5H 2 O (100 l) and sodium ascorbate (100 l) were added. Catalytic amount of Cu (0) was added. The reaction mixture was stirred for 12 h at room temperature. After the reaction was completed, it was S12
13 extracted with CH 2 Cl 2 and water. Organic layer was collected and dried with Na 2 SO 4, evaporated under reduced pressure. The product was purified by silica gel column chromatography using EtOAc/MeOH (85/15; v/v) as mobile phase. Fraction containing Gate 2 was collected, then the solvent was removed under reduced pressure (38 mol, 65 mg, 88%). 1 H NMR (CDCl 3, 400 MHz, ppm) 8.12 (d, 2H, J = Hz; ArH), 7.73 (d, 2H, J = 7.00 Hz; ArH), 7.63 (d + d, 2H + 4H; ArH), (m, 8H), 6.98 (d, 4H, J = 8.76 Hz; ArH), 6.13 (s, 2H; CH), 5.30 (s, 2H; OCH 2 ), 5.29 (s, 2H; OCH 2 ), 4.55 (m, 4H, NCH 2 ), 4.20 (t, 4H, J = 4.88 Hz; OCH 2 ), 3.91 (t, 4H, J = 5.16 Hz; OCH 2 ), 3.78 (m, 4H; OCH 2 ), (m, 8H; OCH 2 ), 3.57 (m, 4H; OCH 2 ), 3.40 (s, 6H; OCH 3 ), 2.75 (t, 4H, J = 6.60 Hz; SCH 2 ), 2.53 (s, 6H, ArCH 3 ), 2.30 (m, 4H + 4H; ArCH 2 + CH2), 1.49 (s, 6H; ArCH 3 ), 1.34 (s, 6H; ArCH 3 ), 1.34 (s, 6H; ArCH 3 ), 1.00 (t, J = 7.48 Hz, 6H; CH 3 ). 13 C NMR (CDCl 3, 400 MHz, ppm) 160.0, 159.2, 158.7, 153.6, 148.4, 140.0, 138.9, 138.7, 138.6, 138.4, 129.8, 127.6, 124.1, 116.1, 115.7, 115.3, 115.0, 110.1, 72.0, 70.9, 70.7, 70.6, 70.0, 69.7, 67.6, 62.1, 62.0, 59.0, 48.4, 30.7, 30.3, 17.1, 14.6, 13.9, 12.5, HRMS (TOF-ESI): m/z calcd for C 84 H 98 B 2 Br 2 F 4 N 10 NaO 10 S [M+Na] +, found: [M+Na] +, Δ = 3.27 ppm. 5. References [1] Obert, E.; Bellot, M.; Bouteiller, L.; Andrioletti, F.; Lehen-Ferrenbach, C.; ois Boue, F. J. Am. Chem. Soc. 2007, 129, [2] Bozdemir, O. A.; Erbas-Cakmak, S.; Ekiz, O.; Dana, A.; Akkaya, E. U. Angew. Chem. Int. Ed. 2011, 50, [3] Rotaru, A.; Mokhir, A. Nucleic Acid Binders Activatd by Light of Selectible Wavelength Angew. Chem. Int. Ed. 2007, 46, [4] Erbas, S.; Gorgulu, A.; Kocakusakogullari, M.; Akkaya, E. U. Chem. Commun. 2009, S13
14 6. NMR Spectra 1 H NMR of compound 3 13 C NMR of compound 3 S14
15 1 H NMR of compound D 13 C NMR of compound D S15
16 1 H NMR of compound A 1 13 C NMR of compound A 1 S16
17 1 H NMR of compound 6 13 C NMR of compound 6 S17
18 1 H NMR of compound 7 13 C NMR of compound 7 S18
19 1 H NMR of compound 8 13 C NMR of compound 8 S19
20 1 H NMR of compound 9 13 C NMR of compound 9 S20
21 1 H NMR of BOD 1 13 C NMR of BOD 1 S21
22 1 H NMR of Compound C NMR of Compound 11 S22
23 1 H NMR of Compound A 2 13 C NMR of Compound A 2 S23
24 1 H NMR of BOD 2 13 C NMR of Compound BOD2 S24
25 7. High Resolution Mass Spectra HRMS of Compound A 1 HRMS of Compound 6 HRMS of Compound 7 S25
26 HRMS of Compound 9 HRMS of BOD 1 HRMS of Compound 11 S26
27 HRMS of BOD 2 S27
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