Supporting Information. Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N'-(het)aryl- N'-[2-nitro(het)aryl]hydrazides
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1 Supporting Information Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N'-(het)aryl- N'-[2-nitro(het)aryl]hydrazides Andrey A. Berezin, Georgia Zissimou, Christos P. Constantinides, Yassine Beldjoudi, Jeremy M. Rawson, Panayiotis A. Koutentis *, Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, Ontario, Canada N9B 3P4 S1
2 Supporting Information Table of Contents Page Figures S1-S13. Solid-State and Solution EPR Spectra of New Radicals 1c-o S3-S21 Table T1. Spin Densities (ρ) Estimated from Hyperfine Coupling Constants using McConnell s Equation b NMR Spectra. 1 H and 13 C NMR Spectra for All New Compounds Figures S14-S26. Cyclic Voltammograms of Radicals 1c-o S22 S23 S78-S84 S2
3 Figure S1. EPR spectra of radical 1c. Solution: g = , a N(1) /G = 7.68, a N(2) /G = 4.84, a N(4) /G = 4.90, a F /G = 0.54, ΔH pp /G = Solution (2 nd deriv.): a N(1) /G = 7.69, a N(2) /G = 4.75, a N(4) /G = 5.00, a F /G = 0.73, ΔH pp /G = S3
4 Solid-State: g = S4
5 Figure S2. EPR spectra of radical 1d. Solution: g = , a N(1) /G = 7.81, a N(2) /G = 4.83, a N(4) /G = 5.07, ΔH pp /G = Solid-State: g = S5
6 Figure S3. EPR spectra of radical 1e. Solution: g = , a N(1) /G = 7.69, a N(2) /G = 4.57, a N(4) /G = 5.13, ΔH pp /G = Solid-State: g = S6
7 Figure S4. EPR spectra of radical 1f. Solution: g = , a N(1) /G = 7.82, a N(2) /G = 4.94, a N(4) /G = 4.95, ΔH pp /G = Solid-State: g = S7
8 Figure S5. EPR spectra of radical 1g. Solution: g = , a N(1) /G = 7.97, a N(2) /G = 4.23, a N(4) /G = 5.03, a F(7) /G = 3.14 ΔH pp /G = Solution (2 nd deriv.): a N(1) /G = 7.97, a N(2) /G = 4.37, a N(4) /G = 5.36, a F(7) /G = 3.02, ΔH pp /G = S8
9 Solid-State: g = S9
10 Figure S6. EPR spectra of radical 1h. Solution: g = , a N(1) /G = 8.07, a N(2) /G = 4.21, a N(4) /G = 5.36, a F(3) /G = 1.89 ΔH pp /G = Solution (2 nd deriv.): a N(1) /G = 8.07, a N(2) /G = 4.19, a N(4) /G = 5.31, a F(3) /G = 1.26, ΔH pp /G = S10
11 Solid-State: g = S11
12 Figure S7. EPR spectra of radical 1i. Solution: g = , a N(1) /G = 6.64, a N(2) /G = 4.38, a N(4) /G = 4.38, a F(3) /G = 4.39, a F(7) /G = 4.44 ΔH pp /G = Solution (2 nd deriv.): a N(1) /G = 8.13, a N(2) /G = 2.70, a N(4) /G = 3.62, a F(3) /G = 4.02, a F(7) /G = 4.75, ΔH pp /G = S12
13 Solid-State: g = S13
14 Figure S8. EPR spectra of radical 1j. Solution: g = , a N(1) /G = 7.51, a N(2) /G = 4.94, a N(4) /G = 5.13, ΔH pp /G = Solid-State: g = S14
15 Figure S9. EPR spectra of radical 1k. Solution: g = , a N(1) /G = 6.89, a N(2) /G = 4.95, a N(4) /G = 5.08, ΔH pp /G = Solid-State: g = S15
16 Figure S10. EPR spectra of radical 1l. Solution: g = , a N(1) /G = 7.12, a N(2) /G = 4.89, a N(4) /G = 5.26, ΔH pp /G = Solid-State: g = S16
17 Figure S11. EPR spectra of radical 1m. Solution: g = , a N(1) /G = 6.74, a N(2) /G = 4.88, a N(4) /G = 4.93, ΔH pp /G = Solid-State: g = S17
18 Figure S12. EPR spectra of radical 1n. Solution: g = , a N(1) /G = 6.88, a N(2) /G = 4.81, a N(4) /G = 4.81, a N(8) /G = 2.00, ΔH pp /G = Solution (2 nd deriv.): a N(1) /G = 7.12, a N(2) /G = 4.81, a N(4) /G = 5.13, a N(8) /G = 1.94, ΔH pp /G = S18
19 Solid-State: g = S19
20 Figure S13. EPR spectra of radical 1o. Solution: g = , a N(1) /G = 6.88, a N(2) /G = 4.20, a N(4) /G = 4.44, a F(7) /G = 4.38 ΔH pp /G = Solution (2 nd deriv.): a N(1) /G = 6.88, a N(2) /G = 4.25, a N(4) /G = 4.32, a F(7) /G = 4.32, ΔH pp /G = S20
21 Solid-State: g = S21
22 Table T1. Spin densities (ρ) estimated from hyperfine coupling constants using McConnell s equation a Radical N1 N2 N4 1c c b d e f g g b h h b i i b j k l m n n b o o b a a N = Q N ρ N, where a N are the hfcc in Gauss; Q N = 21.2 G (for N2 and N4) and Q N = 25 G (for N1). b Simulated second derivative EPR spectrum. S22
23 NMR Spectra. 1 H and 13 C NMR Spectra for All New Compounds S23
24 N'-(2-aminophenyl)-N'-phenylbenzohydrazide NH N NH 7.7 O Current Data Parameters NAME Georgia Z EXPNO PROCNO F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG TD zg SOLVENT CDCl3 NS 16 DS 2 SWH Hz FIDRES Hz AQ RG sec 128 DW usec DE 6.50 usec TE K D sec TD0 1 ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB GB Hz PC
25 N'-(2-aminophenyl)-N'-phenylbenzohydrazide NH 2 N NH O Current Data Parameters NAME Georgia Z EXPNO 530 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT CDCl3 NS 5120 DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K CNST CNST D sec D20 TD sec ======== CHANNEL f1 ======== SFO MHz NUC1 13C P usec P usec PLW W ======== CHANNEL f2 ======== SFO MHz NUC2 1H CPDPRG[2 waltz16 PCPD usec PLW W PLW W F2 - Processing parameters SI SF WDW MHz EM SSB 0 LB Hz GB 0 PC 1.40
26 N'-(2-Aminophenyl)-N'-(pyridin-2-yl)picolinohydrazide (12b)
27 N'-(2-Aminophenyl)-N'-(pyridin-2-yl)picolinohydrazide (12b)
28 N'-(2-nitrophenyl)-N'-phenylbenzohydrazide (13a)
29 N'-(2-nitrophenyl)-N'-phenylbenzohydrazide (13a)
30 N'-[2-nitro-5-(trifluoromethyl)phenyl]-N'-phenylbenzohydrazide (13b)
31 N'-[2-nitro-5-(trifluoromethyl)phenyl]-N'-phenylbenzohydrazide F F F Current Data Parameters NAME Andrey EXPNO 232 PROCNO O - N + O N HN O F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT DMSO NS 1000 DS 4 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec DE 6.50 usec TE K CNST CNST D sec D sec TD ======== CHANNEL f1 ======== SFO MHz NUC1 13C P usec P usec PLW W ======== CHANNEL f2 ======== SFO MHz NUC2 1H CPDPRG[2 waltz16 PCPD usec PLW W PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB Hz GB 0 PC
32 4-fluoro-N'-(2-nitrophenyl)-N'-phenylbenzohydrazide
33 4-fluoro-N'-(2-nitrophenyl)-N'-phenylbenzohydrazide
34 N'-(2-nitrophenyl)-N'-phenyl-2-thiophenecarbohydrazide_(13d)
35 N'-(2-nitrophenyl)-N'-phenyl-2-thiophenecarbohydrazide (13d)
36 N'-(2-nitrophenyl)-N'-phenyl-2-pyridinecarbohydrazide N Current Data Parameters NAME Andrey EXPNO 35 PROCNO O - N + O HN N O F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT Acetone NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG 144 DW usec DE 6.50 usec TE K D sec ======== CHANNEL f1 ======== NUC1 1H P1 1 usec PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC
37 N'-(2-Nitrophenyl)-N'-phenylpicolinohydrazide (13e)
38 N'-(2-Nitrophenyl)-N'-phenylacetohydrazide (13f)
39 N'-(2-Nitrophenyl)-N'-phenylacetohydrazide (13f)
40 Current Data Parameters NAME Andrey EXPNO 274 PROCNO 1 F F F N N O - NH O O CH 3 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT DMSO NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG 80.6 DW usec DE 6.50 usec TE K D sec TD ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC
41 F F F O N + O - N NH CH 3 O Current Data Parameters NAME Andrey EXPNO 275 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT DMSO NS 600 DS 4 SWH Hz FIDRES Hz AQ sec RG 1820 DW usec DE 6.50 usec TE K CNST CNST D sec d sec DELTA sec TD0 1 NUC1 13C P usec p usec PLW W SFO MHz CPDPRG2 NUC2 1H PLW W PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB Hz GB 0 PC
42 2,2,2-Trifluoro-N'-(2-nitrophenyl)-N'-phenylacetohydrazide (13h)
43 2,2,2-Trifluoro-N'-(2-nitrophenyl)-N'-phenylacetohydrazide (13h)
44 2,2,2-trifluoro-N'-[2-nitro-5-(trifluoromethyl)phenyl]-N'-phenylacetohydrazide F F F Current Data Parameters NAME Andrey EXPNO 708 PROCNO O - N + O N HN F F O F F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT DMSO NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG DW 80 usec DE 9.00 usec TE K D sec TD ======== CHANNEL f1 ======== NUC1 1H P usec PL db SFO MHz F1 - Acquisition parameters ND0 2 TD 256 SFO MHz FIDRES Hz SW ppm FnMODE undefined F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC F1 - Processing parameters SI 1024 MC2 QF SF MHz WDW SINE SSB 0 LB 0.30 Hz GB 0.1
45 2,2,2-trifluoro-N'-[2-nitro-5-(trifluoromethyl)phenyl]-N'-phenylacetohydrazide F O - F N + F O N HN F F O F Current Data Parameters NAME Andrey EXPNO 710 PROCNO 710 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT DMSO NS DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.00 usec TE K CNST CNST D sec d sec DELTA sec TD0 1 ======== CHANNEL f1 ======== NUC1 13C P usec p usec PL db SFO MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB Hz GB 0 PC
46 N'-(4-Cyanophenyl)-N'-(2-nitrophenyl)benzohydrazide (13j)
47 N'-(4-Cyanophenyl)-N'-(2-nitrophenyl)benzohydrazide (13j)
48 N'-(4-Cyanophenyl)-N'-(2-nitrophenyl)thiophene-2-carbohydrazide (13k)
49 N'-(4-Cyanophenyl)-N'-(2-nitrophenyl)thiophene-2-carbohydrazide (13k)
50 N'-(2-Nitrophenyl)-N'-(pyridin-2-yl)benzohydrazide N N Current Data Parameters NAME Georgia Z EXPNO 535 PROCNO 1 N + O O - NH O F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT NS CDCl3 16 DS 2 SWH Hz FIDRES Hz AQ sec RG 71.8 DW DE usec 6.50 usec TE K D sec TD ======== CHANNEL f1 ======== SFO MHz 6.75NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB LB Hz GB PC
51 N'-(2-nitrophenyl)-N'-(pyridin-2-yl)benzohydrazide EXPNO 544 PROCNO 1 F2 - Acquisition Parameters Date_ Time 9.29 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT CDCl3 NS 105 DS 4 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec DE 6.50 usec TE K CNST CNST D sec D sec TD ======== CHANNEL f1 ======== SFO MHz NUC1 13C P usec P usec PLW W ======== CHANNEL f2 ======== SFO MHz NUC2 1H CPDPRG[2 waltz16 PCPD usec PLW W PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB Hz GB 0 PC
52 N'-(2-Nitrophenyl)-N'-(pyridin-2-yl)picolinohydrazide (13m)
53 N'-(2-Nitrophenyl)-N'-(pyridin-2-yl)picolinohydrazide (13m)
54 N'-[2-Nitro-5-(trifluoromethyl)phenyl]-N'-(pyridin-2-yl)picolinohydrazide (13n)
55 N'-[2-Nitro-5-(trifluoromethyl)phenyl]-N'-(pyridin-2-yl)picolinohydrazide (13n)
56 N'-(3-Nitropyridin-2-yl)-N'-phenylbenzohydrazide Current Data Parameters NAME Georgia Z EXPNO 527 PROCNO 1 N N + O O - N NH O F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT CDCl3 NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG 128 DW usec DE 6.50 usec TE K D sec TD0 1 ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF WDW MHz EM SSB 0 LB 0.30 Hz GB 0 PC
57 N'-(3-nitropyridin-2-yl)-N'-phenylbenzohydrazide N N + O O - N NH O Current Data Parameters NAME Georgia Z EXPNO 528 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT CDCl3 NS 5120 DS 4 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec DE 6.50 usec TE K CNST CNST D sec D sec TD ======== CHANNEL f1 ======== SFO MHz NUC1 13C P usec P usec PLW W ======== CHANNEL f2 ======== SFO MHz NUC2 1H CPDPRG[2 waltz16 PCPD usec PLW W PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB Hz GB 0 PC
58 N'-(3-nitropyridin-2-yl)-N'-(pyridin-2-yl)picolinohydrazide N O 8.8 N 8.7 N N + O NH O N Current Data Parameters NAME Georgia Z EXPNO PROCNO F2 - Acquisition Parameters Date_ Time 6.19 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT DMSO NS 16 DS 2 SWH Hz FIDRES AQ Hz sec RG 32 DW usec DE 6.50 usec TE K D sec TD ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW SSB 0 EM LB GB Hz PC
59 N'-(3-nitropyridin-2-yl)-N'-(pyridin-2-yl)picolinohydrazide Current Data Parameters NAME Georgia Z EXPNO 581 PROCNO 1 N N N + O N NH O - O N F2 - Acquisition Parameters Date_ Time 9.23 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT DMSO NS 3540 DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K CNST CNST D sec D20 TD sec 1 ======== CHANNEL f1 ======== SFO MHz NUC1 13C P usec P usec PLW W ======== CHANNEL f2 ======== SFO MHz NUC2 1H CPDPRG[2 waltz16 PCPD usec PLW W PLW W F2 - Processing parameters SI SF WDW MHz EM SSB 0 LB Hz GB 0 PC 1.40
60 N 0.25 Current Data Parameters NAME Andrey EXPNO 183 PROCNO O - N + O HN O F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT DMSO NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG 114 DW usec DE 6.50 usec TE K D sec TD ======== CHANNEL f1 ======== NUC1 1H P usec PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC
61 O - N + O N HN O DMSO-d DMSO-d Current Data Parameters NAME Andrey EXPNO 184 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT DMSO NS 284 DS 4 SWH Hz FIDRES Hz AQ sec RG 1820 DW usec DE 6.50 usec TE K CNST CNST D sec D sec TD0 1 ======== CHANNEL f1 ======== NUC1 13C P usec P usec PLW W SFO MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PLW W PLW W SFO MHz DMSO-d F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40
62 N'-(4-Cyanophenyl)benzohydrazide N Current Data Parameters NAME Georgia Z EXPNO 551 PROCNO 1 HN NH O F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT DMSO NS 16 DS 2 SWH Hz FIDRES Hz AQ sec RG 32 DW usec DE 6.50 usec TE K D sec TD0 1 ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC
63 N'-(4-Cyanophenyl)benzohydrazide N HN NH O Current Data Parameters NAME Georgia Z EXPNO 552 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG TD jmod SOLVENT DMSO NS 2048 DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K CNST CNST D sec D20 TD sec ======== CHANNEL f1 ======== SFO MHz NUC1 13C P usec P usec PLW W ======== CHANNEL f2 ======== SFO MHz NUC2 1H CPDPRG[2 waltz16 PCPD usec PLW W PLW W F2 - Processing parameters SI SF MHz WDW SSB 0 EM LB Hz GB PC
64 N'-(4-Cyanophenyl)thiophene-2-carbohydrazide N C urrent Data Parameters NA ME Georgia Z EXPNO 573 PRO C NO 1 HN S NH O F2 - A cquisition Parameters Date_ Time INSTRUM spect PRO BHD 5 mm PA BBO BB- PULPRO G zg30 TD SO LV ENT DMSO NS 20 DS 2 SWH Hz FIDRES Hz A Q sec RG 32 DW usec DE 6.50 usec TE K D sec TD ======== C HA NNEL f1 ======== SFO MHz NUC 1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC
65 N'-(4-Cyanophenyl)thiophene-2-carbohydrazide N HN NH O S Current Data Parameters NAME Georgia Z EXPNO 572 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT DMSO NS 256 DS SWH Hz FIDRES Hz AQ sec RG 2050 DW usec DE 6.50 usec TE K CNST2 CNST D sec D sec TD ======== CHANNEL f1 ======== SFO MHz NUC1 13C P usec P usec PLW W ======== CHANNEL f2 ======== SFO MHz NUC2 1H CPDPRG[2 waltz16 PCPD usec PLW W PLW W F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40
66
67
68
69
70 1,3-Di(2-pyrid-2-yl)-1,4-dihydro-1,2,4-benzotriazine (23b)
71 1,3-Di(2-pyrid-2-yl)-1,4-dihydro-1,2,4-benzotriazine (23b)
72 1,3-Di(pyrid-2-yl)-7-(trifluoromethyl)-1,4-dihydro-1,2,4-benzotriazine (23c)
73 1,3-Di(pyrid-2-yl)-7-(trifluoromethyl)-1,4-dihydro-1,2,4-benzotriazine (23c)
74 1,3-Di(pyrid-2-yl)-1,4-dihydro-1,2,4-pyridotriazine Current Data Parameters NAME Georgia Z EXPNO 560 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT CDCl3 NS 28 DS 2 SWH Hz FIDRES Hz AQ sec RG 71.8 DW usec DE 6.50 usec TE K D sec TD ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec PLW W F2 - Processing parameters SI SF MHz WDW SSB 0 EM LB 0.30 Hz GB 0 PC
75 1,3-Di(pyrid-2-yl)-1,4-dihydro-1,2,4-pyridotriazine N N NH N N N Current Data Parameters NAME Georgia Z EXPNO 561 PROCNO 1 F2 - Acquisition Parameters Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG TD jmod SOLVENT CDCl3 NS 1024 DS 4 SWH Hz FIDRES Hz AQ RG sec 2050 DW usec DE 6.50 usec TE K CNST CNST D sec D20 TD sec ======== CHANNEL f1 ======== SFO MHz NUC1 13C P usec P usec PLW W ======== CHANNEL f2 ======== SFO MHz NUC2 1H CPDPRG[2 waltz16 PCPD usec PLW W PLW W F2 - Processing parameters SI SF MHz WDW SSB 0 EM LB Hz GB 0 PC 1.40
76 1,3-Di(pyrid-2-yl)-1,2,4-benzotriazin-7(1H)-one (24)
77 1,3-Di(pyrid-2-yl)-1,2,4-benzotriazin-7(1H)-one (24)
78 Figure S14. Cyclic voltammogram for radical 1c. Figure S15. Cyclic voltammogram for radical 1d.
79 Figure S16. Cyclic voltammogram for radical 1e. Figure S17. Cyclic voltammogram for radical 1f.
80 Figure S18. Cyclic voltammogram for radical 1g. Figure S19. Cyclic voltammogram for radical 1h.
81 Figure S20. Cyclic voltammogram for radical 1i. Figure S21. Cyclic voltammogram for radical 1j.
82 Figure S22. Cyclic voltammogram for radical 1k. Figure S23. Cyclic voltammogram for radical 1l.
83 Figure S24. Cyclic voltammogram for radical 1m. Figure S25. Cyclic voltammogram for radical 1n.
84 Figure S26. Cyclic voltammogram for radical 1o.
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SUPPORTING INFORMATION Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes Eric J. Uzelac, Casey B. McCausland, and Seth C. Rasmussen*
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