tf_template_word_windows_2007 - s3-eu-west …€¦ · web views9–s10. characterization data of ....
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Supporting Information for
Picolinic Diamide Pincers for Transition Metal Complexation and
Their Electrochemical Properties
Supakit Seawpakorn,a Patchanita Thamyongkit,b Wittawat Keawsongsang,b
and Rojrit Rojanathanes*b
Table of Contents
Characterization data of 3 S2–S3
Characterization data of 4 S4–S6
Characterization data of 5 S7–S8
Characterization data of P1 S9–S10
Characterization data of P2 S11–S13
Characterization data of Cu-4 S14
Characterization data of Ni-4 S15–S16
Characterization data of Cu-P1 S17
Characterization data of Ni-P1 S18
Characterization data of Co-P1 S19
Characterization data of Ni-P2 S20
Characterization data of Co-P2 S21
S1
Compound 3
S2
ppm (f1)0.05.010.0
0
1000
2000
3000
4000
5000
6000
ppm (f1)8.509.009.50
-0.50
0.00
0.50
1.00
1.50
2.00
2.50
NOH
O
OH
O
Ia
H2OHa
ppm (f1)050100150200
0
50
100
150
200
carbonyl group
pyridinyl group
DMSO-d6
30
35
40
45
50
55
60
65
70
75
80
85
90
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S3
Compound 4
S4
ppm (f1)7.207.307.407.507.607.707.80
0
50
ppm (f1)0.05.010.0
0
50
100
150
0.78
0.710.74
0.770.840.67
1.76
NNH
O
HN
O
I
N N
a
b c
d
e
fg
8.48 ppmHa
9.23 ppmHb
4.78 ppmHc
7.69 ppmHd
7.37 ppm
He
7.18-7.23 ppmHf
8.69 ppmHg
CDCl3
S5
ppm (f1)050100150200
0
100
200
300
400
500
600
700
carbonyl group
pyridinyl group
CDCl3
methylene group
30
35
40
45
50
55
60
65
70
75
80
85
90%
Ref
lect
ance
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S6
Compound 5
S7
ppm (f1)7.508.008.509.00
0
50
100
150
200
250
300
ppm (f1)0.05.010.0
0
500
1000
1.00
0.95
0.95
0.77
0.940.89
1.93
3.75
NO
NH
O
HN
N N
Si
a
bc
d
ef
g
h
8.51 ppmHg
0.27 ppmHh
4.81 ppm
Hc
9.15-9.22 ppm
Hb
8.33 ppmHa
7.39 ppm
Hd7.69 ppm
He
7.22 ppm
Hf
CDCl3
ppm (f1)050100150200
0
500000
1000000
carbonyl group
pyridinyl group
ethynyl group
CDCl3
methylene group
silyl group
55
60
65
70
75
80
85
90
95
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S8
Compound P1
S9
ppm (f1)7.508.008.50
0
10
20
30
40
50
ppm (f1)0.05.010.0
0
10
20
30
40
50
60
70
80
1.00
1.210.891.241.321.221.301.03
2.52
NO
NH
O
HN
N N
OHO
a
bc
d
ef
g
h
i
10.07-10.13 ppm
Hb
8.50 ppm
Hg
8.26 ppmHa
4.68 ppm
Hc
DMSO-d6
H2O
7.92 ppm
Hi
7.35 ppmHd
7.72-7.79 ppm
He 7.60 ppmHh 7.25-7.30 ppm
Hf
ppm (f1)050100150200
0
100000
200000
300000
400000
500000
ppm (f1)90100110120130140150160170
0
10000
20000
30000
40000
aromatic group
carbonyl
group
ethynyl groupethynyl group
methylene
group
DMSO-d6
45
50
55
60
65
70
75
80
85
90
95
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S10
Compound P2
S11
ppm (f1)7.508.008.509.00
0
50
100
150
200
ppm (f1)0.05.010.0
0
100
200
300
400
500
1.00
2.04
0.930.85
0.981.030.96
NO
NH
O
HN
NO
NH
O
HN
N N
N N
a
bc
d
ef
g
8.51 ppmHg
9.36 ppmHb
8.42 ppmHa
4.80 ppmHc
7.69 ppmHe
7.39 ppmHd
7.21 ppmHf
CDCl3
S12
ppm (f1)050100150200
0
50000
100000
150000
200000
250000
carbonyl group
pyridinyl group
ethynyl group
methylene group
CDCl3
ppm (f1)90100110120130140150160
0
50000
45
50
55
60
65
70
75
80
85
90
95%
Ref
lect
ance
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S13
Compound Cu-4
35
40
45
50
55
60
65
70
75
80
85
90
95
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S14
Compound Ni-4
S15
ppm (f1)0.05.010.0
0
50
100
150
200
NO
N
O
N
N N
I
Ni
a
c
d
ef
g
Hg
Ha
He
Hd
Hf
Hc
CDCl3
ppm (f1)050100150200
0
100000
200000
300000
400000
ppm (f1)50100150
0
5000
10000
15000
20000pyridinyl group
carbonyl group
methylene group
CDCl3
35
40
45
50
55
60
65
70
75
80
85
90
95
100
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S16
Compound Cu-P1
413.
2556
492.
1532
514.
1325
553.
0644
575.
0457
670.
1430
+MS, 0.6-0.7min #(41-43)
0.0
0.5
1.0
1.5
5x10Intens.
100 200 300 400 500 600 700 800 900 m/z
45
50
55
60
65
70
75
80
85
90
95
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S17
Compound Ni-P1
55
60
65
70
75
80
85
90
95
100
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S18
Compound Co-P1
50
55
60
65
70
75
80
85
90
95
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S19
Compound Ni-P2
35
40
45
50
55
60
65
70
75
80
85
90
95
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S20
Compound Co-P2
30
35
40
45
50
55
60
65
70
75
80
85
90
95
%R
efle
ctan
ce
1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)
S21