Supporting Information. Fluorinated Thiophene-Based Synthons: Polymerization of 1,4-Dialkoxybenzene
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1 Supporting Information Fluorinated Thiophene-Based Synthons: Polymerization of 1,4-Dialkoxybenzene and Fluoro-Dithieno-2,1,3-benzothiadiazole by Direct Heteroarylation Carl Roy, 1 Thomas Bura, 1, Serge Beaupré, 1, Marc-André Légaré, 2, Jon-Paul Sun, 3 Ian G. Hill, 3 Mario Leclerc *1 [*] Prof. Mario Leclerc 1) Canada Research Chair on Electroactive and Photoactive Polymers, Department of Chemistry, Université Laval, Quebec City, Quebec, G1V 0A6 (Canada) 2) Institut für Anorganische Chemie, Julius-Maximilians Universität Würzburg, Am Hubland, (Würzburg) 3) Department of Physics, Dalhousie University, Halifax, Nova Scotia, B3H 4R2 (Canada) Mario.Leclerc@chm.ulaval.ca C. Roy, T. Bura and S. Beaupré contributed equally. 1
2 Table of contents 1. 1 H, 19 F and 13 C NMR spectra p3-p15 2. Crystallographic Data p16-p20 3. Computational details p20-p44 4. Additional References p45 2
3 1. 1 H, 19 F and 13 C NMR spectra Figure 1 : 1 H NMR spectra of 2 in acetone-d 6 Figure 2 : 13 C NMR spectra of 2 in acetone-d 6 3
4 Figure 3 : 1 H NMR spectra of 3 in acetone-d 6 Figure 4 : 19 F NMR spectra of 3 in acetone-d 6 4
5 Figure 5 : 13 C NMR spectra of 3 in acetone-d 6 Figure 6 : 1 H NMR spectra of 4 in acetone-d 6 5
6 Figure 7 : 19 F NMR spectra of 4 in acetone-d 6 Figure 8 : 13 C NMR spectra of 4 in acetone-d 6 6
7 Figure 9 : 1 H NMR spectra of 5 in acetone-d 6 Figure 10 : 19 F NMR spectra of 5 in acetone-d 6 7
8 Figure 11 : 13 C NMR spectra of 5 in acetone-d 6 Figure 12 : 1 H NMR spectra of 6 in acetone-d 6 8
9 Figure 13 : 19 F NMR spectra of 6 in acetone-d 6 Figure 14 : 13 C NMR spectra of 6 in acetone-d 6 9
10 Figure 15 : 1 H NMR spectra of 8 in CDCl 3 Figure 16 : 19 F NMR spectra of 8 in CDCl 3 10
11 Figure 17 : 13 C NMR spectra of 8 in CDCl 3 Figure 18 : 1 H NMR spectra of 9 in CDCl 3 11
12 Figure 19 : 19 F NMR spectra of 9 in CDCl 3 Figure 20 : 13 C NMR spectra of 9 in CDCl 3 12
13 Figure 21 : 1 H NMR spectra of M3 in CDCl 3 Figure 22 : 19 F NMR spectra of M3 in CDCl 3 13
14 Figure 23 : 13 C NMR spectra of M3 in CDCl 3 Figure 24 : 1 H NMR spectra of M4 in CDCl 3 14
15 Figure 25 : 19 F NMR spectra of M4 in CDCl 3 Figure 26 : 13 C NMR spectra of M4 in CDCl 3 15
16 2. Crystallographic Data A suitable crystal was selected for each monomer and mounted on a cryoloop on a Bruker Venture Metaljet diffractometer. The crystal was kept at 150 K (M2), 100 K (M3) and 125 K (M4) during data collection. Using Olex2 1, the structure was solved with the XT 2 structure solution program using Intrinsic Phasing and refined with the ShelX 3 (M2) and XL 4 (M3 and M4) refinement package using Least Squares minimization. The selected sample for M4 is a two components twin as detected by the TWINROTMAT routine from the PLATON suite of software Crystallographic Data of M2 (CCDC Deposition Number: ) Crystal Data for M2 C14H4F4N2S3 (M = g/mol): monoclinic, space group P21/c (no. 14), a = (10) Å, b = (7) Å, c = (7) Å, β = (2), V = (8) Å 3, Z = 4, T = 150 K, μ(gakα) = mm -1, Dcalc = g/cm 3, reflections measured ( Θ ), 3031 unique (Rint = , Rsigma = ) which were used in all calculations. The final R1 was (I > 2σ(I)) and wr2 was (all data). 16
17 Table 1: Torsion Angles for M2. A B C D Angle/ A B C D Angle/ S2 C7 C8 F (2) F4 C13 C14 S (2) S2 C7 C8 C9 0.4(3) C4 C5 C6 C1-0.4(4) C1 N1 S1 N2-0.2(2) C4 C5 C6 N (2) C1 C2 C3 C4 0.4(4) C4 C5 C11 S (2) C1 C2 C7 S2 1.1(4) C4 C5 C11 C12 1.5(4) C1 C2 C7 C (3) C5 C11 C12 F3 2.0(4) F1 C8 C9 F2 0.9(5) C5 C11 C12 C (2) F1 C8 C9 C (3) C6 C1 N1 S1 0.2(3) N1 C1 C2 C (2) C6 C1 C2 C3-0.2(4) N1 C1 C2 C7 0.0(4) C6 C1 C2 C (2) N1 C1 C6 N2-0.1(3) C6 N2 S1 N1 0.2(2) N1 C1 C6 C (2) C6 C5 C11 S3 2.1(4) C2 C1 N1 S (2) C6 C5 C11 C (3) C2 C1 C6 N (2) C7 S2 C10 C9 0.2(3) C2 C1 C6 C5 0.2(4) C7 C2 C3 C (3) C2 C3 C4 C5-0.7(4) C7 C8 C9 F (3) C2 C7 C8 F1 0.7(5) C7 C8 C9 C10-0.3(4) C2 C7 C8 C (3) C8 C9 C10 S2 0.0(4) S1 N2 C6 C1-0.1(3) C10 S2 C7 C (2) S1 N2 C6 C (2) C10 S2 C7 C8-0.4(2) F2 C9 C10 S (3) C11 S3 C14 C13 1.0(2) F3 C12 C13 F4 0.7(4) C11 C5 C6 C (2) F3 C12 C13 C (2) C11 C5 C6 N2 1.8(4) C3 C2 C7 S (2) C11 C12 C13 F (2) C3 C2 C7 C8-0.2(4) C11 C12 C13 C14-0.3(4) C3 C4 C5 C6 0.6(4) C12 C13 C14 S3-0.6(3) C3 C4 C5 C (2) C14 S3 C11 C (2) S3 C11 C12 F (2) C14 S3 C11 C12-1.2(2) S3 C11 C12 C13 1.1(3) 17
18 2.2 Crystallographic Data of M3 (CCDC Deposition Number: ) Crystal Data for M3 C14H6F2N2S3 (M = g/mol): monoclinic, space group P21/c (no. 14), a = (7) Å, b = (3) Å, c = (11) Å, β = (3), V = (13) Å 3, Z = 4, T = 100 K, μ(gakα) = mm -1, Dcalc = g/cm 3, reflections measured ( Θ ), 2945 unique (Rint = , Rsigma = ) which were used in all calculations. The final R1 was (I > 2σ(I)) and wr2 was (all data). Table 2: Torsion Angles for M3. A B C D Angle/ A B C D Angle/ S1 N1 C1 C (13) C3 C4 C5 C6 0.4(2) S1 N1 C1 C6 0.21(17) C3 C4 C5 C (15) S1 N2 C6 C1 0.26(17) C4 C5 C6 N (15) S1 N2 C6 C (13) C4 C5 C6 C1 0.3(2) S2 C7 C8 F (14) C4 C5 C11 S (13) S2 C7 C8 C9-0.1(2) C4 C5 C11 C12 3.3(3) S3 C11 C12 F (13) C5 C11 C12 F2 1.3(3) S3 C11 C12 C (19) C5 C11 C12 C (15) F1 C8 C9 C (16) C6 C1 C2 C3 0.5(2) F2 C12 C13 C (15) C6 C1 C2 C (14) N1 S1 N2 C6-0.13(13) C6 C5 C11 S3 4.0(2) N1 C1 C2 C (16) C6 C5 C11 C (16) N1 C1 C2 C7 0.2(2) C7 S2 C10 C9 0.00(15) N1 C1 C6 N2-0.3(2) C7 C2 C3 C (15) N1 C1 C6 C (14) C7 C8 C9 C10 0.1(2) 18
19 N2 S1 N1 C1-0.05(13) C8 C9 C10 S2-0.1(2) C1 C2 C3 C4 0.3(2) C10 S2 C7 C (14) C1 C2 C7 S2 1.0(2) C10 S2 C7 C8 0.06(13) C1 C2 C7 C (17) C11 S3 C14 C (14) C2 C1 C6 N (14) C11 C5 C6 N2 0.6(2) C2 C1 C6 C5-0.8(2) C11 C5 C6 C (14) C2 C3 C4 C5-0.8(3) C11 C12 C13 C14 0.0(2) C2 C7 C8 F1-1.0(3) C12 C13 C14 S3 0.27(19) C2 C7 C8 C (16) C14 S3 C11 C (14) C3 C2 C7 S (13) C14 S3 C11 C (13) C3 C2 C7 C8 2.9(3) 2.3 Crystallographic Data of M4 (CCDC Deposition Number: ) Crystal Data for M4 C14H6F2N2S3 (M = g/mol): monoclinic, space group P21/c (no. 14), a = (5) Å, b = (8) Å, c = (8) Å, β = (3), V = (14) Å 3, Z = 4, T = 125 K, μ(gakα) = mm -1, Dcalc = g/cm 3, reflections measured ( Θ ), 3037 unique (Rint = , Rsigma = ) which were used in all calculations. The final R1 was (I > 2σ(I)) and wr2 was (all data). Table 3: Torsion Angles for M4. A B C D Angle/ A B C D Angle/ S1 N1 C1 C (2) C4 C5 C6 N (3) S1 N1 C1 C6 0.4(3) C4 C5 C6 C1 1.8(4) S1 N2 C6 C1 0.3(3) C4 C5 C11 S3-3.5(4) S1 N2 C6 C (2) C4 C5 C11 C (3) 19
20 S2 C7 C8 C9-0.2(3) C5 C11 C12 C (3) S3 C11 C12 C13 0.3(3) C6 C1 C2 C3-0.9(4) F1 C9 C10 S (2) C6 C1 C2 C (2) F2 C13 C14 S (3) C6 C5 C11 S (2) N1 S1 N2 C6 0.0(2) C6 C5 C11 C12-2.1(5) N1 C1 C2 C (3) C7 S2 C10 C9 0.2(3) N1 C1 C2 C7-0.5(4) C7 C2 C3 C (3) N1 C1 C6 N2-0.5(4) C7 C8 C9 F (3) N1 C1 C6 C (2) C7 C8 C9 C10 0.4(4) N2 S1 N1 C1-0.2(2) C8 C9 C10 S2-0.4(4) C1 C2 C3 C4 1.5(4) C10 S2 C7 C (2) C1 C2 C7 S2 9.5(4) C10 S2 C7 C8 0.0(2) C1 C2 C7 C (3) C11 S3 C14 C13 0.3(3) C2 C1 C6 N (2) C11 C5 C6 N2 1.3(4) C2 C1 C6 C5-0.7(4) C11 C5 C6 C (2) C2 C3 C4 C5-0.4(5) C11 C12 C13 F (3) C2 C7 C8 C (3) C11 C12 C13 C14-0.1(4) C3 C2 C7 S (2) C12 C13 C14 S3-0.2(4) C3 C2 C7 C8 9.5(4) C14 S3 C11 C (2) C3 C4 C5 C6-1.2(4) C14 S3 C11 C12-0.4(2) C3 C4 C5 C (3) 20
21 3. Computational details All calculations were performed using the Gaussian 09 Suite of programs. 6 The B3LYP functional 7,8 was used in combination with the TZVP basis set 9 for all atoms except Pd (DZVP). 10 This method was previously applied by Gorelski to elucidate the selectivity of palladium-catalyzed direct arylation. 11 The transition states were located and confirmed by frequency calculations (single imaginary frequency). The stationary points were characterized as minima by full vibration frequency calculations (no imaginary frequency). All geometry optimizations were carried out without any symmetry constraints. 3.1 Cartesian coordinates for calculated species Model catalyst Pd P C C H C H C H C H C H O O C C H H H C
22 H H H C H H H C H H H Monomers DTBT-H C C C C S H C C C C C C N N S C C S C H
23 C H H H H H H DTBT-benzoF2 C C C C S H C C C C C C N N S C C S C H C H H H H
24 F F DTBT-3-F C C C C S H C C C C C C N N S C C S C H C H F F H H H
25 DTBT-3,4-F2 C C C C S C C C C C C N N S C C S C C H H F F F F H H
26 DTBT-4-F C C C C S C C C C C C N N S C C S C C H H F F H H H H
27 3.2 TS for the CMD activation of the α protons. TS2CH-DTBT-H2 Pd C C C C C C O C P O H H H H H C H H H H C H H H C H
28 H H C H H H C C C C S H C C C C C C N N S H H H C C S C H C H H TS2CH-DTBT-benzoF2 Pd C C C C C C O
29 C P O H H H H H C H H H H C H H H C H H H C H H H C C C C S H C C C C C C N N S H C C
30 S C H C H H F F TS2CH-DTBT-3-F Pd C C C C C C O C P O H H H H H C H H H H C H H H C H H H C H H
31 H C C C C S H C C C C C C N N S C C S C H C H F F H H TS2CH-DTBT-3,4-F2 Pd C C C C C C O C P O H H
32 H H H C H H H H C H H H C H H H C H H H C C C C S C C C C C C N N S C C S C C H F F H
33 H F F TS2CH-DTBT-4-F Pd C C C C C C O C P O H H H H H C H H H H C H H H C H H H C H H H C C C C
34 S C C C C C C N N S C C S C C H H H F F H H
35 TS for the CMD activation of the β protons TS3CH-DTBT-H Pd C C C C C C O C P O H H H H H C H H H H C H H H C
36 H H H C H H H C C C C S H H C C C C C C N N S H H C C S C H C H H TS3CH-DTBT-benzoF2 Pd C C C C C C
37 O C P O H H H H H C H H H H C H H H C H H H C H H H C C C C S H H C C C C C C N N S C
38 C S C H C H H F F TS3CH-DTBT-4-F Pd C C C C C C O C P O H H H H H C H H H H C H H H C H H H C H
39 H H C C C C S H C C C C C C N N S C C S C C H H H H F F
40 TS for the CMD activation of the γ protons TS4CH-DTBT-H Pd C C C C C C O C P O H H H H H C H H H H C H H H C H
41 H H C H H H C C C C S H H C C C C H C N C H N S C C S C H C H H TS4CH-DTBT-3-F Pd C C C C C C O
42 C P O H H H H H C H H H H C H H H C H H H C H H H C C C C S H C C C C C N C N S C C S
43 C H C H H H F F TS for the CMD activation of the phenylic protons on DTBT-H. Pd C C C C C C O C P O H H H H H C H H H C
44 C H C C C H H H C H H H C H H H C C H N N S C C S C H C H H C C S C H C H H
45 4. Additional References [1] O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J A. K. Howard, H. Puschmann, J. Appl. Cryst. 2009, 42, 339. [2] G. M. Sheldrick, Acta Cryst., 2015, A71, 3. [3] G. M. Sheldrick, Acta Cryst., 2015, C71, 3. [4] G. M. Sheldrick, Acta Cryst., 2008, A64, 112. [5] A. L. Spek, Acta Cryst., 2009, D65, 148. [6] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision C.01 (Gaussian Wallingford, CT, 2009) [7] A. D. J. Becke, Chem. Phys., 1993, 98, [8] C. Lee, W. Yang, R. G. Parr, Phys. Rev., 1988, B37, 785. [9] A. Schafer, C. Huber, R. Ahlrichs, J. Chem. Phys., 1994, 100, [10] N. Godbout, D. R. Salahub, J. Andzelm, E. Wimmer, Can. J. Chem., 1992, 70, 560. [11] S. I. Gorelsky, D. Lapointe, K. Fagnou, J. Org. Chem. 2012, 77,
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