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University of Helsinki, Sep 2018 – Aug 2019 59 Appendix 1. NMR data Figure 6.1.1. 1 H NMR of methyl 3-amino-4-bromobenzoate (48).
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59
Appendix 1. NMR data
Figure 6.1.1. 1H NMR of methyl 3-amino-4-bromobenzoate (48).
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60
Figure 6.1.2. 1H NMR of 2-bromo-4,5-dimethoxyaniline (50).
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61
Figure 6.1.3. 1H NMR of 1,2-dimethoxy-4-nitro-5-(phenylethynyl)benzene (51).
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62
Figure 6.1.4. 1H NMR of 4,5-dimethoxy-2-(phenylethynyl)aniline (52).
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63
Figure 6.1.5. 13
C NMR of 4,5-dimethoxy-2-(phenylethynyl)aniline (52).
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64
Figure 6.1.6. 1H NMR of methyl 4-[(4-methoxyphenyl)ethynyl]-3-nitrobenzoate (53).
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65
Figure 6.1.7. 13
C NMR of methyl 4-[(4-methoxyphenyl)ethynyl]-3-nitrobenzoate (53).
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66
Figure 6.1.8. 1H NMR of methyl 3-amino-4-[(4-methoxyphenyl)ethynyl]benzoate (54).
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67
Figure 6.1.9. 13
C NMR of methyl 3-amino-4-[(4-methoxyphenyl)ethynyl]benzoate (54).
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68
Figure 6.1.10. 13
C DEPT-135 NMR of methyl 3-amino-4-[(4-methoxyphenyl)ethynyl]benzoate (54).
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69
Figure 6.1.11. 1H-
13C HSQC NMR of methyl 3-amino-4-[(4-methoxyphenyl)ethynyl]benzoate (54).
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70
Figure 6.1.12. 1H NMR of tert-butyl [4,5-dimethoxy-2-(phenylethynyl)phenyl]carbamate (55).
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71
Figure 6.1.13. 13
C NMR of tert-butyl [4,5-dimethoxy-2-(phenylethynyl)phenyl]carbamate (55).
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72
Figure 6.1.14. 13
C DEPT-135 NMR of tert-butyl [4,5-dimethoxy-2-(phenylethynyl)phenyl]carbamate (55).
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73
Figure 6.1.15. 1H NMR of N-[4,5-dimethoxy-2-(phenylethynyl)phenyl]-4-methylbenzenesulfonamide (56).
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74
Figure 6.1.16. 13
C NMR of N-[4,5-dimethoxy-2-(phenylethynyl)phenyl]-4-methylbenzenesulfonamide (56).
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75
Figure 6.1.17. 13
C DEPT-135 NMR of N-[4,5-dimethoxy-2-(phenylethynyl)phenyl]-4-methylbenzenesulfonamide
(56).
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76
Figure 6.1.18. 1H NMR of 2-(phenylethynyl)aniline (58).
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77
Figure 6.1.19. 13
C NMR of 2-(phenylethynyl)aniline (58).
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78
Figure 6.1.20. 1H NMR of methyl 2-(4-methoxyphenyl)indole-6-carboxylate (59).
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79
Figure 6.1.21. 1H NMR of 5,6-dimethoxy-2-phenylindole (60).
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80
Figure 6.1.22. 13
C NMR of 5,6-dimethoxy-2-phenylindole (60).
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81
Figure 6.1.23. 1H NMR of tert-butyl 2-phenylindole-1-carboxylate (62).
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82
Figure 6.1.24. 13
C NMR of tert-butyl 2-phenylindole-1-carboxylate (62).
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83
Figure 6.1.25. 1H NMR of 1-[(4-methylphenyl)sulfonyl]-2-phenylindole (63).
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84
Figure 6.1.26. 13
C NMR of 1-[(4-methylphenyl)sulfonyl]-2-phenylindole (63).
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85
Figure 6.1.27. 13
C DEPT-135 NMR of 1-[(4-methylphenyl)sulfonyl]-2-phenylindole (63).
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86
Figure 6.1.28. 1H NMR of 1-tert-butyl 2-ethyl 6-methoxyindole-1,2-dicarboxylate (65).
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87
Figure 6.1.29. 13
C NMR of 1-tert-butyl 2-ethyl 6-methoxyindole-1,2-dicarboxylate (65).
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88
Figure 6.1.30. 13
C DEPT-135 NMR of 1-tert-butyl 2-ethyl 6-methoxyindole-1,2-dicarboxylate (65).
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89
Figure 6.1.31. 1H-
1H COSY NMR of 1-tert-butyl 2-ethyl 6-methoxyindole-1,2-dicarboxylate (65).
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90
Figure 6.1.32. 1H NMR of tert-butyl 3-bromo-2-phenylindole-1-carboxylate (66).
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91
Figure 6.1.33. 13
C NMR of tert-butyl 3-bromo-2-phenylindole-1-carboxylate (66).
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92
Figure 6.1.34. 13
C DEPT-135 NMR of tert-butyl 3-bromo-2-phenylindole-1-carboxylate (66).
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93
Figure 6.1.35. 1H NMR of 3-bromo-1-[(4-methylphenyl)sulfonyl]-2-phenylindole (67).
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94
Figure 6.1.36. 13
C NMR of 3-bromo-1-[(4-methylphenyl)sulfonyl]-2-phenylindole (67).
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95
Figure 6.1.37. 13
C DEPT-135 NMR of 3-bromo-1-[(4-methylphenyl)sulfonyl]-2-phenylindole (67).
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96
Figure 6.1.38. 1H NMR of 3-bromo-1-methyl-2-phenylindole (69).
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97
Figure 6.1.39. 13
C NMR of 3-bromo-1-methyl-2-phenylindole (69).
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98
Figure 6.1.40. 13
C DEPT-135 NMR of 3-bromo-1-methyl-2-phenylindole (69).
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99
Figure 6.1.41. 1H NMR of ethyl 3-bromoindole-2-carboxylate (71).
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100
Figure 6.1.42. 13
C NMR of ethyl 3-bromoindole-2-carboxylate (71).
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101
Figure 6.1.43. 13
C DEPT-135 NMR of ethyl 3-bromoindole-2-carboxylate (71).
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102
Figure 6.1.44. 1H-
1H COSY NMR of ethyl 3-bromoindole-2-carboxylate (71).
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103
Figure 6.1.45. 1H NMR of 1-tert-butyl 2-ethyl 3-bromoindole-1,2-dicarboxylate (72).
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104
Figure 6.1.46. 13
C NMR of 1-tert-butyl 2-ethyl 3-bromoindole-1,2-dicarboxylate (72).
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105
Figure 6.1.47. 13
C DEPT-135 NMR of 1-tert-butyl 2-ethyl 3-bromoindole-1,2-dicarboxylate (72).
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106
Figure 6.1.48. 1H NMR of tris(3,5-dimethoxyphenyl)amine (76).
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107
Figure 6.1.49. 13
C NMR of tris(3,5-dimethoxyphenyl)amine (76).
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108
Figure 6.1.50. 13
C DEPT-135 NMR of tris(3,5-dimethoxyphenyl)amine (76).
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109
Figure 6.1.51. 1H NMR of 2,4,6-trimethylbenzoyl chloride (74).
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110
Figure 6.1.52. 1H NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium tetrafluoroborate
(77).
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111
Figure 6.1.53. 13
C NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium
tetrafluoroborate (77).
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112
Figure 6.1.54. 19
F NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium
tetrafluoroborate (77).
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113
Figure 6.1.55. 13
C DEPT-135 NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium
tetrafluoroborate (77).
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114
Figure 6.1.56. 1H-
1H COSY NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium
tetrafluoroborate (77).
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115
Figure 6.1.57. 1H NMR of 1,1'-methylenebis(2-bromo-4-tert-butylbenzene) (79).
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116
Figure 6.1.58. 13
C NMR of 1,1'-methylenebis(2-bromo-4-tert-butylbenzene) (79).
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117
Figure 6.1.59. 13
C DEPT-135 NMR of 1,1'-methylenebis(2-bromo-4-tert-butylbenzene) (79).
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118
Figure 6.1.60. 1H-
1H COSY NMR of 1,1'-methylenebis(2-bromo-4-tert-butylbenzene) (79).
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119
Figure 6.1.61. 1H NMR of bis(2-bromo-4-tert-butylphenyl)methanol (80).
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120
Figure 6.1.62. 13
C NMR of bis(2-bromo-4-tert-butylphenyl)methanol (80).
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121
Figure 6.1.63. 13
C DEPT-135 NMR of bis(2-bromo-4-tert-butylphenyl)methanol (80).
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122
Figure 6.1.64. 1H-
1H COSY NMR of bis(2-bromo-4-tert-butylphenyl)methanol (80).
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123
Figure 6.1.65. 1H NMR of bis(2-bromo-4-tert-butylphenyl)methanone (81).
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124
Figure 6.1.66. 13
C NMR of bis(2-bromo-4-tert-butylphenyl)methanone (81).
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125
Figure 6.1.67. 13
C DEPT-135 NMR of bis(2-bromo-4-tert-butylphenyl)methanone (81).
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126
Figure 6.1.68. 1H-
1H COSY NMR of bis(2-bromo-4-tert-butylphenyl)methanone (81).
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127
Figure 6.1.69. 1H NMR of 3,6-di-tert-butyl-10-phenylacridin-9(10H)-one (82).
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128
Figure 6.1.70. 13
C NMR of 3,6-di-tert-butyl-10-phenylacridin-9(10H)-one (82).
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129
Figure 6.1.71. 13
C DEPT-135 NMR of 3,6-di-tert-butyl-10-phenylacridin-9(10H)-one (82).
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130
Figure 6.1.72. 1H-
1H COSY NMR of 3,6-di-tert-butyl-10-phenylacridin-9(10H)-one (82).
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131
Figure 6.1.73. 1H NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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132
Figure 6.1.74. 13
C NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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133
Figure 6.1.75. 19
F NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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134
Figure 6.1.76. 13
C DEPT-135 NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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135
Figure 6.1.77. 1H-
1H COSY NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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136
Figure 6.1.78. 1H NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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137
Figure 6.1.79. 13
C NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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138
Figure 6.1.80. 13
C DEPT-135 NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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139
Figure 6.1.81. 13
C DEPT-90 NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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140
Figure 6.1.82. 1H-
1H COSY NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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141
Figure 6.1.83. 1H-
1H NOESY NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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142
Figure 6.1.84. 1H-
13C HSQC NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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143
Figure 6.1.85. 1H-
13C HMBC NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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144
Figure 6.1.86. 1H NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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145
Figure 6.1.87. 13
C NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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146
Figure 6.1.88. 13
C DEPT-135 NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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147
Figure 6.1.89. 1H-
1H COSY NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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148
Figure 6.1.90. 1H-
1H NOESY NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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149
Figure 6.1.91. 1H-
13C HSQC NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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150
Figure 6.1.92. 1H-
13C HMBC NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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151
Figure 6.1.93. 1H NMR of 1-methyl-3-(1-methylpyrrol-2-yl)-2-phenylindole (86).
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152
Figure 6.1.94. 1H NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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153
Figure 6.1.95. 13
C NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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154
Figure 6.1.96. 13
C DEPT-135 NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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155
Figure 6.1.97. 1H-
1H COSY NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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156
Figure 6.1.98. 1H-
1H NOESY NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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157
Figure 6.1.99. 1H-
13C HSQC NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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158
Figure 6.1.100. 1H-
13C HMBC NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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159
Figure 6.1.101. 1H NMR of tert-butyl 3-(5-methylfuran-2-yl)-2-phenylindole-1-carboxylate (89).
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160
Figure 6.1.102. 1H-
1H COSY NMR of tert-butyl 3-(5-methylfuran-2-yl)-2-phenylindole-1-carboxylate (89).
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161
Figure 6.1.103. 1H-
1H NOESY NMR of tert-butyl 3-(5-methylfuran-2-yl)-2-phenylindole-1-carboxylate (89).
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162
Figure 6.1.104. 1H NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-carboxylate (91).
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163
Figure 6.1.105. 13
C NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-carboxylate (91).
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164
Figure 6.1.106. 13
C DEPT-135 NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-
carboxylate (91).
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165
Figure 6.1.107. 13
C DEPT-90 NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-
carboxylate (91).
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166
Figure 6.1.108. 1H-
1H COSY NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-carboxylate
(91).
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167
Figure 6.1.109. 1H-
1H NOESY NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-
carboxylate (91).
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168
Figure 6.1.110. 1H-
13C HMBC NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-
carboxylate (91).
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169
Figure 6.1.111. 1H NMR of 3-bromo-2-phenylindole (88).
