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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

Transcript of 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

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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

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%R

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ctan

ce

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S3

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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

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S5

ppm (f1)050100150200

0

100

200

300

400

500

600

700

carbonyl group

pyridinyl group

CDCl3

methylene group

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65

70

75

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85

90%

Ref

lect

ance

1000 1500 2000 2500 3000 3500 4000 Wavenumbers (cm-1)

S6

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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

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%R

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S8

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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

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S10

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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

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S12

ppm (f1)050100150200

0

50000

100000

150000

200000

250000

carbonyl group

pyridinyl group

ethynyl group

methylene group

CDCl3

ppm (f1)90100110120130140150160

0

50000

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95%

Ref

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ance

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S13

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Compound Cu-4

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S14

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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

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%R

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S16

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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

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ce

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S17

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Compound Ni-P1

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S18

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Compound Co-P1

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S19

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Compound Ni-P2

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S20

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Compound Co-P2

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S21