Ullmann-Type Intramolecular C-O Reaction Toward Thieno[3,2-b]furan Derivatives with up to Six Fused Rings
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1 Ullmann-Type Intramolecular C-O Reaction Toward Thieno[3,2-b]furan Derivatives with up to Six Fused Rings Daoliang Chen,, Dafei Yuan,, Cheng Zhang,, Hao Wu,, Jianyun Zhang,, Baolin Li*, and Xiaozhang Zhu*,, School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing , P. R. China Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing , P. R. China S1
2 Table of contents 1. Synthesis of compounds 3... S3 2. Optimization of the reaction conditions of 4l... S5 3. Proposed mechanism for intramolecular C-O Ullmann reaction... S6 4. DFT calculations... S7 5. CV spectra of C8-DTBDF... S9 6. OFET research of C8-DTBDF... S10 7. X-ray crystallographic analysis of BTBFs... S11 8. NMR spectra... S16 S2
3 1. Synthesis of compounds 3 Synthesis of compound 3a 3m: Table S1. The reaction substrate scope. Entry Product Yield (%) 1 3a b c d e f g h 78 S3
4 9 3i j k l m 81 Reaction conditions for general Suzuki coupling for synthesis of compounds 3: Compounds 1 (1 mmol), compounds 2 (1.5 mmol), Pd(PPh3)4, K2CO3 (4 mol), 1,4-dioxane (10 ml) and H2O (2 ml), 90 o C, 12 h. All reactions were conducted at 90 o C under N2 atmosphere. S4
5 2. Optimization of the reaction conditions of 4l Table S2. Optimization of the reaction conditions of 4l. Entry Metal Ligand Solvent Base Yield Time 1 CuI phen DMF K2CO3 18% 15 min 2 CuI phen DMF KOAc n.d. 15 min 3 CuI phen DMF NaHCO3 63% 1 h 4 CuI phen DMF LiOH trace 15 min 5 CuI phen DMF NaH2PO4 n.d. overnight All reactions were conducted at 90 o C under N2 atmosphere. S5
6 3. Proposed mechanism for intramolecular C-O Ullmann reaction Figure S1. Proposed mechanism for intramolecular Ullmann reaction. The proposed mechanism of the Ullmann reaction are widely believed to include two typical pathways, one is the radical mechanism, and the other is the Cu(III) mechanism. To gain mechanistic insights, we added 3 equivalent of butylated hydroxytoluene (BHT) as a radical quencher under the optimized reaction condition. The formation of the desired product was not inhibited, which suggests that no radical pathway was involved in the reaction. Therefore, we supposed that the reaction mechanism is an oxidative addition to form an aryl-cu(iii) phenoxide complex (C) that undergoes reductive elimination of the furan ring. As shown in Figure S1, firstly, intermediate A (the neutral form) was formed in the presence of base, which is in an equilibrium with the ion form B. Next, the copper(i) insertion of C-Br formed intermediate C (Cu III ) from intermediate A, and then reductive elimination occurred to afford the intramolecular cyclization product 4. S6
7 4. DFT calculations DFT calculation of BTBF Table S3. B3LYP/6-31G optimized standard orientation of BTBF Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z SCF Done: E(RB3LYP) = A.U. after 1 cycle Convg = D-08 -V/T = DFT calculation of BTBT Table S4. B3LYP/6-31G optimized standard orientation of BTBT Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S7
8 SCF Done: E(RB3LYP) = A.U. after 15 cycles Convg = D-08 -V/T = S8
9 5. CV spectra of C8-DTBDF Measurements were carried out in a one-compartment cell under N2 atmosphere, equipped with a glassy-carbon electrode, a carbon counter electrode, and a Ag/AgCl reference electrode. The supporting electrolyte was a 0.1 mol/l dichloromethane solution of tetrabutylammonium perchlorate (TBAP). All potentials were corrected against Fc/Fc +. CV was measured with a scan rate of 100 mv/s. Figure S2. Cyclic voltammogram of C8-DTBDF in CH2Cl2 (HOMO: 5.42 ev). S9
10 6. OFET research of C8-DTBDF Table S5. OFET device performance Annealing Temperature Hole Mobility (cm 2 V 1 s 1 ) Avg (Max) Threshold Voltage (V) Avg (Min) Ion/Ioff Avg (Max) RT ( ) 14 ( 12) 10 5 (10 5 ) ( ) 22 ( 16) 10 5 (10 6 ) ( ) 23 ( 18) 10 4 (10 4 ) Figure S3. FET transfer characteristics and output curve. The highest occupied molecular orbital (HOMO) energy level of C8-DTBDF is determined by means of cyclic voltammetry (Figure S1) to be 5.42 ev below the vacuum level, which is suitable for OFET application. Bottom-gate bottom-contact OFETs were fabricated to investigate the semiconducting properties of C8-DTBDF. The semiconducting layers were spin-coated (in cholorform) onto octadecyltrichlorosilane-modified SiO2 (300 nm)/si substrates with pre-patterned gold source and drain electrodes. S10
11 7. X-ray crystallographic analysis of BTBFs X-ray crystallographic data of BTBF (4a), Cl-BTBF (4j), tbu-btbf (4d) and C8-DTBDF are listed in the Table S5. Table S6. X-ray crystallographic data of BTBF (4a) (CCDC No.: ), Cl-BTBF (4j) (CCDC No.: ), tbu-btbf (4d) (CCDC No.: ) and C8-DTBDF (CCDC No.: ). Compound 4a 4d CCDC No. CCDC CCDC Empirical formula C18 H16 O S C18 H16 O S Formula weight Temperature K K Wavelength Å Å Crystal system, space group Monoclinic, C 1 2/c 1 Monoclinic, P 1 21/c 1 Unit cell dimensions a = (14) Å = 90 b = 5.267(3) Å = (8) c = (9) Å = 90 a = (5) Å = 90 b = 5.977(3) Å = (6) c = (9) Å = 90 Volume 2002(2) Å (11) Å 3 Z, Calculated density 8, Mg/m 3 4, Mg/m 3 Absorption coefficient mm mm -1 F(000) Crystal size mm mm Theta range for data collection to deg to deg. Limiting indices -30<=h<=30, -6<=k<=6, -20<=l<=20-15<=h<=15, -7<=k<=7, -25<=l<=25 Reflections collected/unique 6561/2229 [R(int) = ] 9763/3135 [R(int) = ] Absorption correction Semi-empirical from equivalents Semi-empirical from equivalents Max. and min. transmission and and Refinement method Full-matrix least-squares on F 2 Full-matrix least-squares on F 2 Data / restraints / parameters 2229 / 0 / / 0 / 184 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R1 = , wr2 = R indices (all data) R1 = , wr2 = R1 = , wr2 = Largest diff. peak and hole and e.å and e. Å -3 S11
12 Compound 4j C8-DTBDF CCDC No. CCDC CCDC Empirical formula C14H7ClOS C30H38O2S2 Formula weight Temperature 173 K K Wavelength Å Å Crystal system, Monoclinic Triclinic space group P P -1 Unit cell dimensions a = (8) Å = 90 b = 3.842(2) Å = (14) c=13.114(10)å = 90 a = 6.657(3) Å = (7). b=8.177(4)å = (4). c = (5) Å = (8). Volume 536.0(6) Å (5) Å 3 Z, Calculated density 2, Mg/m 3 1, Mg/m 3 Absorption coefficient mm mm -1 F(000) Crystal size 0.23 x 0.12 x 0.07 mm x 0.08 x 0.03 mm 3 Theta range for data collection Limiting indices to to <=h<=14, -4<=k<=4, -16<=l<=17-8<=h<=8, -10<=k<=10, -16<=l<=16 Reflections collected/unique 6227 / 2394 [R(int) = ] 9042 / 3013 [R(int) = ] Absorption correction Semi-empirical from Semi-empirical from equivalents equivalents Max. and min. transmission and and Refinement method Full-matrix least-squares on F 2 Full-matrix least-squares on F 2 Data / restraints / parameters 2394 / 1 / / 0 / 155 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R1 = , wr2 = R indices (all data) R1 = , wr2 = R1 = , wr2 = Largest diff. peak and hole and e.å and e.å -3 S12
13 Thermal ellipsoid plots (50 % probability level) of BTBF (4a), Cl-BTBF (4j), tbu-btbf (4d) and C8-DTBDF are shown below. Figure S4. Thermal ellipsoid plots (50 % probability level) of BTBF (4a) Figure S5. Thermal ellipsoid plots (50 % probability level) of tbu-btbf (4d). Figure S6. Thermal ellipsoid plots (50 % probability level) of Cl-BTBF (4j). Figure S7. Thermal ellipsoid plots (50 % probability level) of C8-DTBDF. The packing mode of BTBF (4a) S13
14 Figure S8. The packing mode of BTBF (4a). The packing mode of BTBT is also included for comparison. The molecules of BTBF (4a) stack as a herringbone structure by C-H π (2.738 Å) interactions, and the π-π interaction distance is 3.41 Å, besides there is also substantial S-S interactions 3.47 Å, the O H bond distances between the neighboring molecules are 2.84 Å. The packing mode of 4d Figure S9. The packing mode of 4d. The packing structure of 4d is very interisting each two molecules packing by π-π interactions and dipole interactions with the distance 3.65 Å, and the packing structure of each dimer stacked by C-H π interactions with the distance 2.87 Å. S14
15 The packing mode of 4j Figure S10. The packing mode of 4j. 4j exhibits highly coplanar-conjugated frameworks due to the sulfur and oxygen bridges. The dihedral angle between the two outer benzene rings is only 0.5. The molecules arrange into a herringbone motif along the b-axis with an angle of 81.2 between the adjacent BTBF backbones. S S nonbonding interactions (3.473 Å) was observed along a-axis. Introduction of a chlorine substituent on BTBF backbone strongly influences the crystal packing. In the packing of 4j, each molecule stacks in a parallel fashion along b-axis with the interplane distance of about 3.46 Å and the tilt angle of about The adjacent stacks were linked through S S (3.555 Å) and S H nonbonding interactions to form a compressed highly ordered packing mode, which makes 4j an attractive candidate for device applications. S15
16 8. NMR spectra 2-(3-Bromobenzo[b]thiophene-2yl)phenol) (3a). S16
17 S17
18 2-(3-Bromothiophen-2-yl)phenol (3b) S18
19 S19
20 2-(3-Bromo-6-(tert-butyl)benzo[b]thiophen-2-yl)phenol (3c) S20
21 S21
22 2-(3-Bromobenzo[b]thiophene-2-yl)-5-(tert-butyl)phenol (3d) S22
23 S23
24 2-(3-Bromo-6-(tert-butyl)benzo[b]thiophen-2-yl)-5-(tert-butyl)phenol (3e) S24
25 S25
26 2-(3-Bromobenzo[b]thiophen-2-yl)-4-fluorophenol (3f) S26
27 S27
28 1-(2,3-Dibromobenzo[b]thiophen-6-yl)octan-1-one (3g) S28
29 S29
30 4-Bromo-2-(3-bromobenzo[b]thiophen-2-yl)phenol (3h) S30
31 S31
32 2-(3,6-Dibromobenzo[b]thiophen-2-yl)phenol (3i) S32
33 S33
34 2-(3-Bromobenzo[b]thiophen-2-yl)-4-chlorophenol (3j) S34
35 S35
36 2-(3-Bromo-5-chlorobenzo[b]thiophen-2-yl)phenol (3k) S36
37 S37
38 2-(3-bromo-5-chlorobenzo[b]thiophen-2-yl)-4-chlorophenol (3l) S38
39 S39
40 2-(3-bromo-5-chlorobenzo[b]thiophen-2-yl)-4-fluorophenol (3m) S40
41 S41
42 2,5-Bis(3-bromothiophen-2-yl)benzene-1,4-diol (3n) S42
43 S43
44 2,2 -(3,6-Dibromothieno[3,2-b]thiophene-2,5-diyl)diphenol (3o) S44
45 S45
46 Benzo[4,5]thieno[3,2-b]benzofuran (4a) S46
47 S47
48 Thieno[3,2-b]benzofuran (4b) S48
49 S49
50 2-(Tert-butyl)benzo[4,5]thieno[3,2-b]benzofuran (4c) S50
51 S51
52 7-(Tert-butyl)benzo[4,5]thieno[3,2-b]benzofuran (4d) S52
53 S53
54 2,7-Di-tert-butylbenzo[4,5]thieno[3,2-b]benzofuran (4e) S54
55 S55
56 8-Fluorobenzo[4,5]thieno[3,2-b]benzofuran (4f) S56
57 S57
58 1-(Benzo[4,5]thieno[3,2-b]benzofuran-2-yl)octan-1-one (4g) S58
59 S59
60 8-Bromobenzo[4,5]thieno[3,2-b]benzofuran (4h) S60
61 S61
62 2-Bromobenzo[4,5]thieno[3,2-b]benzofuran (4i) S62
63 S63
64 8-Chlorobenzo[4,5]thieno[3,2-b]benzofuran (4j) S64
65 S65
66 3-Chlorobenzo[4,5]thieno[3,2-b]benzofuran (4k) S66
67 S67
68 3,8-Dichlorobenzo[4,5]thieno[3,2-b]benzofuran (4l) S68
69 S69
70 3-Chloro-8- fluorobenzo[4,5]thieno[3,2-b]benzofuran (4m) S70
71 S71
72 DTBDF S72
73 S73
74 TTDBF S74
75 S75
76 C8-DTBDF S76
77 S77
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