Plate 1: 1H NMR spectrum of pyridyl[1,5-a]-4-phenylimidazolium chloride (4.3a)

10 9 8 7 6 5 4 3 2 1 ppm

0.98

1.05

2.98

2.97

0.95

0.95

1.00

7'

N+

N1

2

3

45

6

7

8

9

10

1112

10

11

Plate 1a:13C NMR spectrum of pyridyl[1,5-a]-4-phenylimidazolium chloride (4.3a)

130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

114115116117118119120121122123124125126127128129130131132133134135136 ppm

Plate 1b: 13C Dept 135 NMR spectrum of pyridyl[1,5-a]-4-phenylimidazolium chloride (4.3a)

130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

113114115116117118119120121122123124125126127128129130131 ppm

Plate 1c: IR spectrum of pyridyl[1,5-a]-4-phenylimidazolium chloride (4.3a)

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650.0

84.5

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99.3

cm-1

%T

vmz-53.4b (H)

3063.45

1614.82

1510.75

1075.14

759.63

693.24

Plate 1d: HRMS spectrum of pyridyl[1,5-a]-4-phenylimidazolium chloride (4.3a)

Plate 2: 1H NMR spectrum of pyridyl[1,5-a]-4-phenylimidazolium chloride (4.3b)

10 9 8 7 6 5 4 3 2 1 ppm

1.02

1.04

2.04

2.99

0.96

1.09

1.00

7'

N+

N

F

12

3

45

6

7

8

9

10

11

12

10

11

Plate 2a: 13C NMR spectrum of pyridyl[1,5-a]-4-(p-fluoro)phenylimidazolium chloride (4.3b)

102030405060708090100110120 ppm

115120125130135140145150155160 ppm

Plate 2b: IR spectrum of pyridyl[1,5-a]-4-(p-fluoro)phenylimidazolium chloride (4.3b)

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400.0

30.1

35

40

45

50

55

60

65

70

75

80

85

90

95

100

105

110

115

120

125

130

135.8

cm-1

%T

vmz-54.2b (F)

3353.39

3066.91

2059.16

1627.05

1545.76

1509.48

1344.80

1234.24

1163.57

1107.061081.88

1011.06

853.33

809.27787.87

742.61

554.75

456.92

Plate 2c: HRMS spectrum of pyridyl[1,5-a]-4-(p-fluoro)phenylimidazolium chloride (4.3b)

Plate 3: 1H NMR spectrum of pyridyl[1,5-a]-4-(p-chloro)phenylimidazolium chloride (4.3c)

10 9 8 7 6 5 4 3 2 1 ppm

0.98

1.05

1.99

3.06

0.95

1.05

1.00

7'

N+

N

Cl

12

3

45

67

8

9

10

11

12

10

11

Plate 3a: 13C NMR spectrum of pyridyl[1,5-a]-4-(p-chloro)phenylimidazolium chloride (4.3c)

102030405060708090100110120130 ppm

Plate 3b: IR spectrum of pyridyl[1,5-a]-4-(p-chloro)phenylimidazolium chloride (4.3c)

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650.0

80.06

80.5

81.0

81.5

82.0

82.5

83.0

83.5

84.0

84.5

85.0

85.5

86.0

86.5

87.0

87.5

88.0

88.5

89.0

89.5

90.0

90.5

91.0

91.5

92.0

92.5

93.093.32

cm-1

%T

vmz-69.2d (Cl)

3379.90

3056.80

1656.65

1546.87

1504.66

1421.01

1342.25

1211.82

1095.05

1071.89

1011.10

839.21

811.55

745.35

Plate 3c: HRMS spectrum of pyridyl[1,5-a]-4-(p-chloro)phenylimidazolium chloride (4.3c)

Plate 4: 1H NMR spectrum of pyridyl[1,5-a]-4-(p-bromo)phenylimidazolium chloride (4.3d)

10 9 8 7 6 5 4 3 2 1 ppm

1.04

1.18

2.07

3.18

1.03

0.99

1.00

7'

N+

N

Br

12

3

45

67

8

9

10

11

12

10

11

Plate 4a: 13C NMR spectrum of pyridyl[1,5-a]-4-(p-bromo)phenylimidazolium chloride (4.3d)

130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 4b: IR spectrum of pyridyl[1,5-a]-4-(p-bromo)phenylimidazolium chloride (4.3d)

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650.0

47.5

50

52

54

56

58

60

62

64

66

68

70

72

74

76

78

80

82

84.1

cm-1

%T

vmz-55.2b (Br)

3369.56

3063.36

2075.76

1655.13

1545.111500.15

1416.78

1341.61

1260.72

1212.06

1120.61

1066.48

1008.67

948.27

835.75

805.73

744.21

711.62

Plate 4b: IR spectrum of pyridyl[1,5-a]-4-(p-bromo)phenylimidazolium chloride (4.3d)

Plate 5: 1H NMR spectrum of pyridyl[1,5-a]-4-(o-methyl)phenylimidazolium chloride (4.3e)

10 9 8 7 6 5 4 3 2 1 ppm

3.17

1.03

1.08

1.06

3.00

1.07

0.97

1.03

1.00

7'

13

14

15N+

NCH31

2

3

45

67

8

9

10

1112

Plate 5a: 13C NMR spectrum of pyridyl[1,5-a]-4-(o-methyl)phenylimidazolium chloride (4.3e)

130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 6: 1H NMR spectrum of pyridyl[1,5-a]-4-(m-methyl)phenylimidazolium chloride (4.3f)

10 9 8 7 6 5 4 3 2 1 ppm

3.25

0.99

1.04

0.99

1.03

1.02

1.01

1.09

1.01

1.08

1.00

7'

13

1415

N+

N

CH3

12

3

45

67

8

9

10

1112

Plate 6a: 13C NMR spectrum of pyridyl[1,5-a]-4-(m-methyl)phenylimidazolium chloride (4.3f)

140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 7: 1H NMR spectrum of pyridyl[1,5-a]-4-(p-methyl)phenylimidazolium chloride (4.3g)

10 9 8 7 6 5 4 3 2 1 ppm

3.37

1.01

1.06

2.06

2.07

1.11

0.98

1.06

1.00

7'

13

N+

N

CH3

12

3

45

67

8

9

10

1112

10

11

Plate 7a: 13C NMR spectrum of pyridyl[1,5-a]-4-(p-methyl)phenylimidazolium chloride (4.3g)

140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 8: 1H NMR spectrum of pyridyl[1,5-a]-4-(p-anisy)phenylimidazolium chloride (4.3h)

10 9 8 7 6 5 4 3 2 1 ppm3.

32

3.11

1.18

2.05

1.12

1.02

1.07

1.00

7'

13

N+

N

O CH3

12

3

45

6

7

8

9

10

11

12

10

11

Plate 9: 1H NMR spectrum of pyridyl[1,5-a]-4-(p-nitro)phenylimidazolium chloride (4.3i)

10 9 8 7 6 5 4 3 2 1 ppm

0.95

1.04

1.11

1.93

2.92

1.08

1.00

7'

N+

N

NO2

12

3

45

6

7

8

9

10

11

12

10

11

Plate 9a: 13C NMR spectrum of pyridyl[1,5-a]-4-(p-nitro)phenylimidazolium chloride (4.3i)

140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 10: 1H NMR spectrum of pyridyl[1,5-a]-4-sulfanilamidylimidazolium chloride (4.3j)

10 9 8 7 6 5 4 3 2 1 ppm

1.02

1.10

1.05

4.02

2.18

1.00

7'

N+

N

SNH2

O

O

12

3

45

6

7

8

9

10

11

12

10

11

Plate 10a: 13C NMR spectrum of pyridyl[1,5-a]-4-sulfanilamidylimidazolium chloride (4.3j)

140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 10b: IR spectrum of pyridyl[1,5-a]-4-sulfanilamidylimidazolium chloride (4.3j)

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650.0

52.1

54

56

58

60

62

64

66

68

70

72

74

76

78

80

82

84

86

88

90

92

94.2

cm-1

%T

vmz-74.2e (SO2NH2)

3091.17

1656.60

1593.211546.52

1506.07

1424.95

1336.75

1285.841236.83

1193.35

1167.82

1097.43

1076.71

1020.30 922.31

836.19

799.91

736.05

Plate 10c: HRMS spectrum of pyridyl[1,5-a]-4-sulfanilamidylimidazolium chloride (4.3j)

Plate 11: 1H NMR spectrum of pyridyl[1,5-a]-4-sulphapyridylimidazolium chloride (4.3k)

10 9 8 7 6 5 4 3 2 1 ppm

0.97

1.04

1.89

1.03

1.02

1.01

1.94

1.94

1.86

1.00

N+ N S NH

N

O

O12

3

4

56

7

8 9

10 11

12

13 15

14

16

17 18

20

197'

Plate 11a: 13C NMR spectrum of pyridyl[1,5-a]-4-sulphapyridylimidazolium chloride (4.3k)

150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 11b: IR spectrum of pyridyl[1,5-a]-4-sulphapyridylimidazolium chloride (4.3k)

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650.0

70.0

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96.0

cm-1

%T

vmz-76DS.d (SO2-pyridine)-2

3384.17

3057.28

2817.86

1614.41

1536.801509.47

1463.25

1427.43

1388.98

1347.56

1272.20

1244.98

1142.77

1107.87

1086.06

1007.94986.85

962.56

849.17

785.90768.98

747.07

729.52

715.12

Plate 11c: HRMS spectrum of pyridyl[1,5-a]-4-sulphapyridylimidazolium chloride (4.3k)

Plate 12: 1H NMR spectrum of pyridyl[1,5-a]-4-(m-methyl)pheny-5-pyridylimidazolium chloride (4.4a)

3.03.54.04.55.05.56.06.57.07.58.08.59.0 ppm

3.19

1.96

1.15

4.11

1.08

1.20

1.06

0.90

0.91

1.00

7.47.57.67.77.87.98.08.18.28.38.48.58.68.78.88.99.0 ppm

N+

N

CH3

N

12

3

4 5

67

8

9

10

1112

11'

10'13

1'

2'3'

4'

5'6' 7'

H-2 H-2'

H-7

H-5H-4'

H-3'

H-4,10,10',12

H-5'

H-3,11

Plate 12a: 13C NMR spectrum of pyridyl[1,5-a]-4-(m-methyl)pheny-5-pyridylimidazolium chloride (4.4a)

150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 13: 1H NMR spectrum of pyridyl[1,5-a]-4-(p-N,N-Diethyl)pheny-5-pyridylimidazolium chloride (4.4b)

9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

7.36

4.27

0.98

1.09

1.07

1.09

2.10

3.20

1.16

0.91

0.99

1.00

12

3

4 5

6

7

89

10

11

12

13

15

14

N+

N

N

NCH3

CH3

1'

2'3'

4'

5' 6'7'

Plate 13a: 13C Dept 135 NMR spectrum of pyridyl[1,5-a]-4-(p-N,N-Diethyl)pheny-5-pyridylimidazolium chloride (4.4b)

150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

Plate 13b: IR spectrum of pyridyl[1,5-a]-4-(p-N,N-Diethyl)pheny-5-pyridylimidazolium chloride (4.4b)

4000.0 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650.0

58.360

65

70

75

80

85

90

95

100

105

110

115

120

124.5

cm-1

%T

vmz-60.2c (NHEt2)

3372.20

2462.43

1653.06

1586.74

1516.71

1452.70

1422.69

1377.10

1358.68

1323.111276.71

1251.921192.44

1154.671020.56

916.28

842.55787.51

744.74

680.43

Plate 13c: HRMS spectrum of pyridyl[1,5-a]-4-(p-N,N-Diethyl)pheny-5-pyridylimidazolium chloride (4.4b)