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S1

Supporting Information

An efficient multicomponent synthesis of 2,4,5-

trisubstituted and 1,2,4,5-tetrasubstituted imidazoles

catalyzed by a magnetic nanoparticle supported Lewis

acidic deep eutectic solvent.

Thanh Thi Nguyen, Ngoc-Phuong Thi Le, The Thai Nguyen and Phuong Hoang Tran**Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam

National University, Ho Chi Minh City 721337, Vietnam.

Corresponding author: E-mail: thphuong@ hcmus.edu.vn

Table of contents

Section S1. Chemicals and analytical Techniques S2

Section S2. Synthesis of LADES@MNP catalyst S3

Section S3. Spectral data of products S4-S16

Section S4. Copies of 1H and 13C NMR spectra of all products S17- S45

Section S5. References S46 – S47

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2019

S2

Section S1. Chemicals and analytical Techniques

Materials

Imidazole (99%), iron(II) chloride hexahydrate (99%), iron(II) sulfate heptahydrate (99%),

potassium hydroxide (85%), benzyl (≥99%), aniline (≥99,5%), ammonium acetate (≥98%) were

purchased from Acros Organics. Zinc chloride (≥98%), 3-(chloropropyl) trietoxysilane (95%),

benzaldehyde (99%), 2-nitrobenzaldehyde (98%), 4-nitrobenzaldehyde (98%), 3-

hydroxybenzaldehyde (99%), 4-hydroxybenzaldehyde (98%), 2-hydroxybenzaldehyde (97%), 4-

florobenzaldehyde (98%), 4-methylbenzaldehyde (97%), 4-methoxybenzaldehyde (98%), 4-N,N-

dimethylbenzaldehyde (99%), 4-chlorobenzaldehyde (97%), 4-t-butylbenzaldehyde (97%), 2-

carboxybenzaldehyde (97%), 2-methyl-5-hydroxybenzaldehyde (97%) were obtained from

Sigma-Aldrich Chemical Company. Ethyl acetate (≥99,5%), petroleum ether (≥99,5%), sodium

sulfate anhydrous (≥99%) were prepared from Xilong Chemical Co., Ltd. Ethanol (≥99,5%) was

obtained from Chemsol Co., Ltd. TLC (silica gel 60 F254) layer was obtained from Merk.

Analytical Techniques1H and 13C nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Advance II

500 MHz NMR spectrometer. Fourier Transform infrared (FT-IR) spectra were recorded from

KBr pellets using a Bruker Vertex 70 system. Raman spectra were recorded on a Horiba Xplora

One using a 532 nm argon ion laser. ICP-MS was recorded on a PerkinElmer 350X. Thermal

gravimetric analysis (TGA) was performed on a TA Q500 thermal analysis system with the

sample held in a platinum pan in a continuous airflow. TEM was recorder from JEOL JEM-1400

series 100kV Transmission Electron Microscope.

S3

Section S2. Synthesis and characterization of LADES@MNP catalyst

Synthesis of Fe3O4 nanoparticles: The magnetic nanoparticle Fe3O4 was synthesized by co-

precipitation method reported in the literature. The mixture of FeCl2 and FeCl3 was dissolved in

200 mL water under ultrasonic irradiation. The pH value of the solution was adjusted to 12.0 by

adding amount of potassium hydroxide solution (1.0 M). After sonication for 120 mins, Fe3O4

was washed repeatedly water and ethanol, separated with a magnetic and drying at 80 oC for 12

hours.

Coating Fe3O4 nanoparticles of silica: The coating of a layer of silica on the surface of the

nano Fe3O4 was carried out by refluxing the mixture of Fe3O4 (1 g), 3 mL ammonia solution and

3 mL of tetraethylorthosilicate (TEOS) in 100 mL ethanol. After 8 h, the black precipitate

(SiO2@Fe3O4) was collected using a magnet, followed by washing with ethanol three times and

drying at 80 °C for 6 h. 5 g SiO2@Fe3O4 were dispersed in 100 mL toluene by sonication for 30

min and (3-chloropropyl)triethoxysilane (4.820 g, 20.0 mmol) was then added. After refluxing

for 12 hours, the reaction mixture was cooled to room temperature. The product

(Fe3O4@SiO2@(CH2)3Cl ) was separated, wash with ethanol and dried for further application.

Synthesis of LADES: The reaction of urea (20.0 mol) and zinc chloride (5.0 mmol) was

involved at 100 oC and strirring to afford clear solution. DES [Urea]4[ZnCl2] was used without

further purification.

Procedure for the synthesis of LADES@MNP: The mixture of 3.0 g Fe3O4@SiO2@(CH2)3Cl

and DES [Urea]4[ZnCl2] (1.880 g, 5.0 mmol) were added round-bottomed flask and strirred at 90 oC for 18 hours. Lastly, the Fe3O4@SiO2@(CH2)3-Urea-ZnCl2 catalyst was rinsed three times

with ethanol and water, collected magnetically from solution mixture, and dried under reduced

pressure at 60 °C for 6 h.

S4

Figure S1. Raman spectra of LADES@MNP

Figure S2. TG analysis of LADES@MNP

Figure S3. Magnetic curves of Fe3O4 (a) and LADES@MNP (b)

S5

Section S3. Spectral data of products

2,4,5-Triphenyl-1H-imidazole24 (C21H16N2, 1a): Analytical TLC on silica gel, 1:9 ethyl

acetate/hexane; white solid; yield : 123 mg (83%); mp. 276-277 oC (lit. mp. 267-269 oC) ; FT-IR

(KBr) 3417, 3037, 2967, 1600, 1502, 1487, 1460, 766, 696 cm-1; 1H NMR (500 MHz, DMSO-

d6) δ 12.69 (s, 1H), 8.09 (d, J = 7.5 Hz, 2H), 7.55 (d, J =7.5 Hz, 2H), 7.52-7.43 (m, 6H), 7.38

(dd, J = 7.0 Hz, 2H), 7.31 (dd, J = 7.5 Hz, 2H), 7.22 (dd, J = 7.0 Hz, 2H); 13C NMR (125 MHz,

DMSO-d6) δ 145.5, 137.1, 135.2, 131.1, 130.3, 128.7, 128.7, 128.5, 128.2, 128.2, 127.8, 127.1,

126.5, 125.2.

N

NH

2-(4,5-Diphenyl-1H-imidazol-2-yl)phenol24 (C21H16N2O, 1b): Analytical TLC on silica gel, 1:9

ethyl acetate/hexane; white solid; yield: 140 mg (90%); mp. 212-213 oC (lit. mp. 202-205 oC);

FT-IR (KBr) 3421, 3213, 3061, 1607, 1494, 1443, 1383, 1261, 758, 694 cm-1; 1H NMR (500

MHz, DMSO-d6) δ 13.01 (s, 1H),12.93(s, 1H), 8.01 (d, J = 10 Hz, 1H), 7.52-7.40 (m, 7H), 7.32

(dd, J = 7.5 Hz, 2H), 7.26-7.23 (m, 2H), 6.96-6,90 (m, 2H); 13C NMR (125 MHz, DMSO-d6) δ

157.0, 146.2, 134.5, 133.9, 130.6, 130.4, 129.1, 128.9, 128.7, 127.6, 127.4, 127.1, 125.3, 119.2,

117.2, 113.2.

N

NH

OH

3-(4,5-Diphenyl-1H-imidazol-2-yl)phenol33 (C21H16N2O, 1c): Analytical TLC on silica gel, 1:9

ethyl acetate/hexane; white solid; yield: 125 mg (80%); mp. 263-264 oC (lit. mp. 258-260 oC) ;

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FT-IR (KBr) 3372, 3060, 3017, 2914, 1618, 1502, 1230, 1193, 762, 695 cm-1; 1H NMR (500

MHz, DMSO-d6) δ 12.61 (s, 1H), 9.55 (s, 1H), 7.54-7.49 (m, 5H), 7.44 (dd, J = 7.0 Hz, 2H),

7.37 (dd, J = 7.5 Hz, 2H), 7.32-7.20 (m, 4H); 13C NMR (125 MHz, DMSO-d6) δ 157.6, 145.6,

137.0, 135.2, 131.6, 131.1, 129.7, 128.6, 128.5, 128.2, 128.1, 127.7, 127.1, 126.5, 116.1, 115.4,

112.2.

N

NH

OH

4-(4,5-Diphenyl-1H-imidazol-2-yl)phenol24 (C21H16N2O, 1d): Analytical TLC on silica gel, 1:9

ethyl acetate/hexane; yellow solid; yield: 142 mg (91%); mp. 264-265 oC (lit. mp. 232-233 oC);

FT-IR (KBr) 3448, 2952, 2828, 1597, 1474, 1441, 1394, 1317, 1129, 1038, 967, 764, 692 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 12.41 (s, 1H), 9.70 (s, 1H), 7.90 (d, J = 9.0 Hz, 2H), 7.54 (d, J

= 7.5 Hz, 2H), 7.49 (d, J = 7.5 Hz, 2H), 7.44 (d, J = 7.5 Hz, 2H), 7.36 (dd, J = 7.0 Hz, 1H), 7.30

(dd, J = 7.0 Hz, 2H), 7.21(dd, J = 7.0 Hz, 1H), 6.85 (d, J = 8.5 Hz, 2H); 13C NMR (125 MHz,

DMSO-d6) δ 170.0, 157.4, 145.7, 136.3, 135.1, 131.0, 128.3, 128.0, 127.8, 127.2, 127.0, 126.7,

126.5, 126.0, 121.3, 115.1.

N

NH

OH

2-(2-Fluorophenyl)-4,5-diphenyl-1H-imidazole (C21H15FN2, 1e): Analytical TLC on silica gel,

1:9 ethyl acetate/hexane; yellow solid; yield: 119 mg (76%); mp. 217-218 oC; FT-IR (KBr) 3443,

3059, 2952, 2826, 1725, 1641, 1485, 1442, 1382, 1245, 1130, 1041, 766, 699 cm-1; 1H NMR

(500 MHz, DMSO-d6) δ 12.64 (s, 1H), 7.80 (dd, J = 4.0 Hz, 1H), 7.61 (dd, J = 4.0 Hz, 1H),

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7.55 (d, J = 7.5 Hz, 2H), 7.50-7.46 (m, 4H), 7.43 (dd, J = 7.0 Hz, 2H), 7.36 (dd, J = 7.0 Hz,

2H), 7.31 (dd, J = 7.5 Hz, 2H), 7.23 (dd, J = 7.0 Hz, 1H) ppm; 13C NMR (125 MHz, DMSO-d6)

δ 143.7, 136.3 (d, J = 222.5 Hz), 131.9 (d, J = 6.3 Hz), 131.2, 130.6 (d, J = 4.0 Hz), 130.4,

129.0, 128.5, 128.4, 128.1, 127.5 (d, J = 5.0 Hz), 126.9.

N

NH

F

4-(4-Fluorophenyl)-4,5-diphenyl-1H-imidazole35 (C21H15FN2, 1f) Analytical TLC on silica

gel, 1:9 ethyl acetate/hexane; white solid; yield: 100 mg (64%); mp. 253-254 oC; FT-IR (KBr)

3418, 3030, 2856, 1606, 1541, 1494, 1444, 1382, 1322, 1226, 1023, 832, 767, 694 cm-1; 1H

NMR (500 MHz, 13C NMR (125 MHz, DMSO-d6) δ ) δ 12.69 (s, 1H), 8.12 (dd, J1 = 5.5 Hz, J2

= 7.5 Hz, 2H), 7.54 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 7.0 Hz, 2H), 7.45 (dd, J = 7.5 Hz, 2H),

7.39-7.29 (m, 5H), 7.22 (dd, J = 7.5 Hz, 1H); 13C NMR (125 MHz, DMSO-d6) δ 162.1 (d, J =

245.0 Hz), 144.7, 137.1, 135.1, 131.0, 128.7, 128.4, 128.2 (d, J = 30.0 Hz), 127.8, 127.4 (d, J =

7.5 Hz), 127.1, 126.6, 115.7 (d, J = 21.0 Hz).

N

NH

F

2-(4-Nitrophenyl)-4,5-diphenyl-1H-imidazole24 (C21H15N3O2, 1g): Analytical TLC on silica

gel, 1:9 ethyl acetate/hexane; orange solid; yield: 140 mg (82%); mp. 202-203 oC (lit. mp. 199-

201 oC); FT-IR (KBr) 3418, 3030, 2856, 1606, 1541, 1494, 1444, 1382, 1322, 1226, 1023, 832,

768, 694 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 13.50 (s, 1H), 8.40-8.39 (m, 5H), 8.29-8.24 (m,

4H), 7.86-7.81 (m, 3H), 7.72 (d, J = 4Hz, 1H), 7.51-7.46 (m, 2H); 13C NMR (125 MHz, DMSO-

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d6) δ 159.4, 136.9, 132.8, 131.8, 131.2, 130.9, 129.3, 129.0, 128.8, 128.5, 128.2, 127.7, 127.4,

126.5, 126.2, 126.1, 124.1, 122.7.

N

NH

NO2

2-(2-Chlorophenyl)-4,5-diphenyl-1H-imidazole32 (C21H15ClN2, 1h): Analytical TLC on silica

gel, 1:9 ethyl acetate/hexane; white solid; yield: 145 mg (88%); mp. 212-214 oC (lit. mp. 190-

191 oC); FT-IR (KBr) 3415, 2951, 2826, 1601, 1440, 1392, 1315, 1196, 1128, 1038, 966, 907,

763, 691 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 12.64 (s, 1H), 7.81-7.80 (m, 1H), 7.62-7.60

(m,1H); 7.55-7.42 (m, 8H), 7.38-7.29 (m, 3H), 7.23 (dd, J = 7.0 Hz, 1H) ppm; 13C NMR (125

MHz, DMSO-d6) δ 143.1, 136.5, 134.8, 131.3, 131.2, 130.6, 129.9, 129.8, 129.7, 128.3, 127.9,

127.4, 126.9, 126.3.

N

NH

Cl

2-(4-Chlorophenyl)-4,5-diphenyl-1H-imidazole24 (C21H15ClN2, 1i): Analytical TLC on silica

gel, 1:9ethyl acetate/hexane; white solid; yield: 141 mg (85%); mp. 267-268 oC (lit. mp. 262-264 oC) ; FT-IR (KBr) 3415, 1603, 1485, 1433, 1128, 1092, 830, 765, 696 cm-1; 1H NMR (500 MHz,

DMSO-d6) δ 12.78 (s, 1H), 8.09 (d, J = 8.0 Hz, 2H), 7.54-7.43 (m, 7H), 7.39 (d, J = 7.0 Hz, 1H),

7.31 (dd, J = 7.0 Hz, 2H), 7.23 (d, J = 7.0 Hz, 1H) ppm; 13C NMR (125 MHz, DMSO-d6) δ

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144.7, 137.6, 135.3, 133.1, 131.2, 129.5, 129.1, 129.0, 128.9, 128.8, 128.5, 128.2, 127.4, 127.2,

127.0.

N

NH

Cl

2-(4-Methoxyphenyl)-4,5-diphenyl-1H-imidazole24 (C22H18N2O, 1k): Analytical TLC on silica

gel, 1:9 ethyl acetate/hexane; white solid; yield: 137 mg (84%); mp. 258-259 oC (lit. mp. 220-

223 oC); FT-IR (KBr) 3416, 2959, 2837, 1612, 1492, 1443, 1249, 1200, 1030, 968, 829, 765, 695

cm-1; 1H NMR (500 MHz, DMSO-d6) δ 12.51 (s, 1H), 8.01 (d, J = 8.0 Hz, 2H), 7.54 (d, J = 7.5

Hz, 2H), 7.49 (d, J = 7.5 Hz, 2H), 7.43 (dd, J = 7.0 Hz, 2H), 7.36 (dd, J = 7.5 Hz, 1H), 7.30 (dd,

J = 7.5 Hz, 2H), 7.21 (dd, J = 7.5 Hz, 1H), 7.04 (d, J = 7.5 Hz, 2H), 3.81 (s, 3H); 13C NMR (125

MHz, DMSO-d6) δ 159.4, 145.6, 136.8, 135.3, 131.2, 128.6, 128.4, 128.2, 127.6, 127.6, 127.0,

126.7, 126.4, 123.1, 114.1, 55.2.

N

NH

O

4-(4,5-Diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline33 (C23H21N3, 1l): Analytical TLC on

silica gel, 1:9 ethyl acetate/hexane; white solid; yield: 149 mg (88%); mp. 258-259 oC (lit. mp.

256-259 oC); FT-IR (KBr) 3417, 2797, 1616, 1496, 1444, 819, 765, 696 cm-1; 1H NMR (500

MHz, DMSO-d6) δ 12.31 (s, 1H), 7.90 (d, J = 9.0 Hz, 2H), 7.53 (d, J = 7.0 Hz, 2H), 7.48 (d, J =

7.0 Hz, 2H), 7.42 (t, J = 7.0 Hz, 2H), 7.35 (d, J = 7.0 Hz, 1H), 7.29 (t, J = 7.0 Hz, 2H), 7.21 (d, J

= 7.0 Hz, 1H), 6.79 (d, J = 9.0 Hz, 2H), 2.96 (s, 6H); 13C NMR (125 MHz, DMSO-d6) δ 150.3,

146.5, 136.5, 135.5, 131.4, 128.6, 128.3, 128.1, 127.4, 127.0, 126.3, 118.3, 111.9, 39.9.

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N

NH

N

2-(4-(tert-Butyl)phenyl)-4,5-diphenyl-1H-imidazole (C24H22N2, 1m): Analytical TLC on silica

gel, 1:9 ethyl acetate/n-hexane; white solid; yield: 165 mg (94%); mp. 285-286 oC; FT-IR (KBr)

3416, 3057, 2963, 2867, 1603, 1492, 1450, 1385, 1268, 976, 838, 765, 696 cm-1; 1H NMR (500

MHz, DMSO-d6) δ 12.61 (s, 1H), 8.01 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 7.0 Hz, 2H), 7.50 (d, J =

6.0 Hz, 4H), 7.44 (d, J = 7.0 Hz, 2H), 7.38 (d, J = 7.0 Hz, 1H), 7.30 (dd, J = 7.0 Hz, 2H), 7.23

(d, J = 7.0 Hz, 1H), 1.32 (s, 9H); 13C NMR (125 MHz, DMSO-d6) δ 151.1, 145.9, 137.3, 135.6,

131.5, 129.0, 128.8, 128.5, 128.3, 128.0, 127.4, 126.8, 125.7, 125.3, 34.76, 31.4.

N

NH

4,5-Diphenyl-2-(p-tolyl)-1H-imidazole24 (C22H18N2, 1n): Analytical TLC on silica gel, 1:9ethyl

acetate/hexane; white solid; yield: 147 mg (95%); mp. 231-232 oC (lit. mp. 233-235 oC); FT-IR

(KBr) 3416, 3028, 1602, 1493, 1449, 1384, 1322, 1200, 1127, 968, 822, 765, 695 cm-1; 1H NMR

(500 MHz, DMSO-d6) δ 12.59 (s, 1H), 7.97 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 7.5 Hz, 2H), 7.51

(d, J = 7.5 Hz, 2H), 7.44 (dd, J = 7.5 Hz, 2H), 7.37 (dd, J = 7.5 Hz, 1H), 7.31-7.28 (m, 4H),

7.22 (dd, J = 7.5 Hz, 1H), 2.35 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 146.0, 138.0, 137.2,

135.6, 131.5, 129.6, 129.0, 128.7, 128.5, 128.3, 128.0, 127.4, 126.8, 125.5, 21.2.

S11

N

NH

3-(4,5-Diphenyl-1H-imidazol-2-yl)-1H-indole (C23H17N3, 1o): Analytical TLC on silica gel,

1:9 ethyl acetate/hexane; white solid; yield: 156 mg (93%); mp. 306-307 oC; FT-IR (KBr) 3413,

3049, 2959, 1606, 1492, 1443, 1335, 1245, 846, 757, 694 cm-1; 1H NMR (500 MHz, DMSO-d6)

δ 12. 27 (s, 1H), 11.37 (s, 1H), 8.48 (d, J = 7.5 Hz, 1H), 8.00 (s, 1H), 7.64 (d, J = 7.5 Hz, 2H),

7.52 (d, J = 7.0 Hz, 2H), 7.46-7.43 (m, 3H), 7.37-7.31 (m, 3H), 7.23-7.14 (m, 3H); 13C NMR

(125 MHz, DMSO-d6) δ 143.4, 135.9, 135.6, 135.4, 131.3, 128.4, 127.8, 127.1, 126.6, 125.8,

125.4, 124.8, 123.4, 121.5, 121.2, 119.4, 111.3, 106.5.

N

NH NH

1,2,4,5-Tetraphenyl-1H-imidazole32 (C27H20N2, 2a): Analytical TLC on silica gel, 1:9 ethyl

acetate/hexane; white solid; yield: 136 mg (73%), mp. 213-217 oC; FT-IR (KBr, 4000-400 cm-

1): 3419, 3054, 1594, 1490, 1446, 1320 cm-1; 1H NMR (500 MHz, CDCl3-d1) 7.43-7.42 (m,

8H), 7.42-7.04 (m, 11H); 13C NMR (125 MHz, CDCl3-d1) 147.1, 137.3, 134.6, 131.3, 131.0,

130.9, 130.7, 129.2, 129.1, 128.6, 128.5, 128.4, 128.3, 128.2, 128.1, 128.0, 127.6, 126.7, 125.4.

S12

N

N

2-(2-Hydroxyphenyl)-1,4,5-triphenyl imidazole17 (C27H20N2O, 2b): Analytical TLC on silica

gel, 1:9 ethyl acetate/hexane; white solid; yield: 151 mg (78%), mp. 250-254 oC; FT-IR (KBr)

3420, 3060, 2930, 1645, 1591, 1487, 1381, 1252 cm-1; 1H NMR (500 MHz, DMSO-d6) 12.57

(s, 1H), 7.45-7.29 (m, 16H), 6.94 (d, J = 8.0 Hz, 1H), 6.67-6.62 (m, 1H), 6.55 (t, J = 8.0 Hz, 1H); 13C NMR (125 MHz, DMSO-d6) 157.3, 144.4, 136.6, 134.4, 133.2, 131.3, 130.8, 130.2, 129.6,

129.4, 129.3, 128.7, 128.7, 128.5, 128.4, 126.9, 126.8, 126.1, 118.1, 116.9, 113.9.

N

N

OH

2-(3-Hydroxyphenyl)-1,4,5-triphenyl imidazole34 (C27H20N2O, 2c): Analytical TLC on silica


3400, 3057, 1594, 1490, 1448, 1396, 1320 cm-1; 1H NMR (500 MHz, DMSO-d6) 9.50 (s, 1H),

7.48 (d, J = 7.7 Hz, 2H), 7.32-7.15 (m, 13H), 7.17 (t, J = 7.1 Hz, 1H), 6.68 (t, J = 8.7 Hz, 2H); 13C NMR (125 MHz, DMSO-d6) 157.1, 146.1, 136.7, 136.7, 134.4, 131.5, 131.2, 131.2, 130.4,

129.1, 129.1, 128.7, 128.4, 128.4, 128.2, 126.4, 126.3, 118.9, 115.4, 115.4.

S13

N

NOH

2-(4-Hydroxyphenyl)-1,4,5-triphenyl imidazole32 (C27H20N2O, 2d): Analytical TLC on silica


3423, 2923, 1598, 1456, 1379, 1270 cm-1; 1H NMR (500 MHz, DMSO-d6) 9.67 (s, 1H), 7.47-

7.22 (m, 17H), 6.65 (s, 2H); 13C NMR (125 MHz, DMSO-d6) 157.6, 146.4, 136.9, 136.4,

134.6, 131.1, 130.6, 130.6, 129.8, 129.1, 128.8, 128.6, 128.4, 128.3, 128.1, 126.3, 121.3, 114.9.

N

N

OH

2-(2-Nitrophenyl)-1,4,5-triphenyl imidazole33 (C27H19N3O2, 2e): Analytical TLC on silica gel,

1:9 ethyl acetate/hexane; white solid; yield: 146 mg (70%); mp. 213-216 oC; FT-IR (KBr) 3427,

3060, 1593, 1509, 1398, 1343 cm-1; 1H NMR (500 MHz, CDCl3-d1) 7.90 (d, J = 8.0 Hz, 1H),

7.67 (d, J = 7.5 Hz, 1H), 7.60 (dd, J = 19.9, 7.5 Hz, 3H), 7.50 (t, J = 8.0 Hz, 1H), 7.26-7.14 (m,

11H), 6.94 (d, J = 7.5 Hz, 2H); 13C NMR (125 MHz, CDCl3-d1) 149.3, 143.7, 139.1, 136.1,

134.6, 133.8, 133.3, 131.4, 131.0, 130.7, 130.3, 129.3, 128.8, 128.6, 128.4, 127.8, 127.1, 127.0,

124.8.

S14

N

N

NO2

2-(4-Nitrophenyl)-1,4,5-triphenyl imidazole33 (C27H19N3O2, 2f): Analytical TLC on silica gel,

1:9 ethyl acetate/hexane; white solid; yield: 188 mg (90%), mp. 194-198 oC; FT-IR (KBr) 3430,

3054, 2926, 2851, 1594, 1449, 1339, 1241 cm-1; 1H NMR (500 MHz, DMSO-d6) 8.15 (d, J =

8.5 Hz, 2H), 7.62 (d, J = 8.5 Hz, 2H), 7.51 (d, J = 7.5 Hz, 2H), 7.39-7.27 (m, 12H), 7.21 (t, J =

7.5 Hz, 1H).; 13C NMR (125 MHz, DMSO-d6) 146.7, 143.8, 137.8, 136.3, 136.2, 133.9, 132.8,

131.1, 129.9, 129.5, 129.3, 128.8, 128.7, 128.6, 128.5, 128.3, 126.8, 126.4, 123.5.

N

N

NO2

2-(4-Florophenyl)-1,4,5-triphenyl imidazole (C27H19N2F, 2g): Analytical TLC on silica gel,


3050, 1596, 1487,1378, 1224 cm-1; 1H NMR (500 MHz, DMSO-d6) 7.48 (d, J = 8.0 Hz, 2H),

7.42-739 (m, 2H), 7.34-7.23 (m, 6H), 7.27-7.23 (m, 6H), 7.19-7.13 (m, 6H); 13C NMR (125

MHz, DMSO-d6) 161.9 (d, J = 246.25 Hz), 145.2, 136.8, 136.5, 135.6, 134.3, 131.3, 131.1,

130.5, 130.4, 130.5, 130.3, 129.5 (d, J = 11.13 Hz), 129.2, 128.8, 128.7, 128.5, 128.4, 128.2,

126.9 (d, J = 3.38 Hz), 126.5, 126.3, 115.2 (d, J = 21.5 Hz).

S15

N

N

F

2-(4-Chlorophenyl)-1,4,5-triphenyl imidazole32 (C27H19N2Cl, 2h): Analytical TLC on silica


3057, 1595, 1487, 1404 cm-1; 1H NMR (500 MHz, DMSO-d6) 7.49 (d, J = 8.0 Hz, 2H), 7.37-

7.24 (m, 16H), 7.18 (dd, J = 7.5 Hz, 1H); 13C NMR (125 MHz, DMSO-d6) 145.4, 137.5,

136.9, 134.7, 133.6, 132.1, 131.6, 130.7, 130.3, 129.7, 129.7, 129.4, 129.2, 129.0, 128.9, 128.8,

128.7, 127.0, 126.8.

N

N

Cl

2-(4-Methoxyphenyl)-1,4,5-triphenyl imidazole32 (C28H22N2O, 2k): Analytical TLC on silica


3417, 3053, 2945, 1603, 1484, 1378, 1247 cm-1; 1H NMR (500 MHz, DMSO-d6) 7.48 (d, J =

7.5 Hz, 2H), 7.34-728 (m, 8H), 7.24 (dd, J = 7.5 Hz, 6H), 7.16 (dd, J = 7.5 Hz, 1H), 6.84 (d, J =

8.5 Hz, 2H), 3.72 (s, 3H); 13C NMR (125 MHz, DMSO-d6) 159.2, 146.0, 136.8, 136.5, 134.5,

131.1, 130.8, 130.5, 129.6, 129.1, 128.8, 128.7, 128.4, 128.3, 128.1, 126.3, 122.8, 113.6, 55.1.

S16

N

N

O

2-(4-N,N-dimethylaminophenyl)-1,4,5-triphenyl imidazole (C29H25N3, 2l): Analytical TLC on

silica gel, 1:9 ethyl acetate/hexane; white solid; yield: 187 mg (90%), mp. 207-209 oC; FT-IR

(KBr) 3416, 2804, 1608, 1488, 1439, 1367, 1194 cm-1; 1H NMR (500 MHz, DMSO-d6) 7.47

(d, J = 7.5 Hz, 2H), 7.33-7.27 (m, 7H), 7.23-7.17 (m, 8H), 6.57 (d, J = 8.5 Hz, 2H), 2.88 (s, 6H); 13C NMR (125 MHz, DMSO-d6) 149.9, 146.7, 137.1, 136.3, 134.7, 131.2, 130.7, 130.4, 129.1,

129.0, 128.8, 128.5, 128.4, 128.2, 128.1, 126.3, 126.2, 117.7, 111.3.

N

N

N

2-(2-Carboxyphenyl)-1,4,5-triphenyl imidazole (C28H20N2O2, 2m): Analytical TLC on silica


3416, 3059, 2848, 1598, 1497, 1368, 1238 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 7.90-7.83 (m,

3H), 7.64 (t, J = 6.0 Hz, 1H), 7.52-7.51 (m, 7H), 7.40-7.37 (m, 5H), 7.33-7.31 (m, 3H); 13C NMR

(125 MHz, DMSO-d6) δ 169.0, 144.9, 132.7, 130.7, 130.2, 129.0, 128.8, 128.6, 128.5, 127.6,

127.3.

S17

N

N

COOH

2-(4-tert-Butylphenyl)-1,4,5-triphenyl imidazole (C31H29N2, 2o): Analytical TLC on silica gel,


3056, 2957, 1598, 1491, 1266 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 7.48 (d, J = 7.5 Hz, 2H),

7.35-7.15 (m, 17H), 1.24 (s, 9H); 13C NMR (125 MHz, DMSO-d6) δ 150.8, 146.0, 136.8, 136.7,

134.5, 131.2, 131.2, 130.5, 129.2, 128.8, 128.5, 128.4, 128.2, 127.9, 127.6, 126.5, 126.4, 125.0,

34.4, 31.0.

N

N

2-(4-Methylphenyl)-1,4,5-triphenyl imidazole33 (C28H22N2, 2p): Analytical TLC on silica gel,


3047, 2920, 1593, 1489, 1442, 1377, 1320 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 7.50-7.47 (m,

2H), 7.31 (m, 6H), 7.27-7.24 (m, 9H), 7.09 (d, J = 8.0 Hz, 2H), 2.26 (s, 3H); 13C NMR (125

MHz, DMSO-d6) δ 146.1, 137.8, 136.7, 136.7, 134.5, 131.1, 131.1, 130.5, 129.1, 128.8, 128.7,

128.7, 128.4, 128.4, 128.2, 128.1, 127.6, 126.4, 126.4, 20.7.

N

N

S18

2-(2-Hydroxy-5-methylphenyl)-1,4,5-triphenyl imidazole (C28H23N2O, 2q): Analytical TLC

on silica gel, 1:9 ethyl acetate/hexane; white solid; yield: 187 mg (93%), mp. 200-202 oC; FT-IR

(KBr) 3428, 3055, 2914, 2793, 1596, 1495, 1379, 1247 cm-1; 1H NMR (500 MHz, DMSO-d6) δ

12.32 (s, 1H), 7.44-7.20 (m, 15H), 6.98 (d, J = 8.0 Hz, 1H), 6.83 (d, J = 8.0 Hz, 1H), 6.40 (s,

1H), 1.89 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 155.1, 144.6, 136.7, 134.4, 133.2, 131.3,

130.7, 130.6, 129.7, 129.3, 129.1, 128.7, 128.7, 128.5, 128.4, 127.2, 126.9, 126.3, 126.1, 116.7,

113.4, 20.1.

N

N

OH

S19

Section S4. Copies of 1H and 13C NMR spectra of all products

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.5

1.002.042.096.172.022.04

7.217.227.247.297.317.327.367.387.397.437.457.467.487.507.527.557.568.088.10

NH

N

0102030405060708090100110120130140150160170180190200210220

125.2

126.5

127.1

127.8

128.2

128.2

128.5

128.6

128.7

130.3

131.1

135.2

137.1

145.5

NH

N

S20

Figure S1. 1H (top) and 13C (bottom) NMR spectra of 2,4,5-triphenyl-1H-imidazole (C21H16N2, 1a)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

1.992.002.017.14

1.00

0.990.94

6.926.967.257.327.467.477.497.50

12.93

13.01

NH

N

OH

102030405060708090100110120130140150160170180190200210220

113.2

117.2

119.2

125.3

127.1

127.4

127.6

128.7

128.9

129.1

130.4

130.6

133.9

134.5

146.2

157.0

NH

N

OH

S21

Figure S2. 1H (top) and 13C (bottom) NMR spectra of 2-(4,5-diphenyl-1H-imidazol-2-yl)phenol (C21H16N2O, 1b)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

3.981.001.985.92

0.93

0.90

6.776.797.207.227.237.247.267.277.297.307.327.357.377.387.427.447.457.497.507.517.537.549.559.55

12.61

NH

N

OH

0102030405060708090100110120130140150160170180190200210220

112.2

115.4

116.1

127.1

128.2

128.5

128.6

129.7

145.6

157.6

NH

N

OH

S22

Figure S3. 1H (top) and 13C (bottom) NMR spectra of 3-(4,5-diphenyl-1H-imidazol-2-yl)phenol (C21H16N2O, 1c)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

2.001.002.071.092.062.062.012.01

1.01

0.99

6.856.867.217.287.307.317.367.427.447.457.487.507.537.557.897.91

9.70

12.41

NH

N

OH

102030405060708090100110120130140150160170180190200210220

115.1

121.3

126.0

126.5

126.7

127.0

127.2

127.8

128.0

128.3

131.0

135.1

136.3

145.7

157.4

170.0

NH

N

OH

S23

Figure S4. 1H (top) and 13C (bottom) NMR spectra of 4-(4,5-diphenyl-1H-imidazol-2-yl)phenol (C21H16N2O, 1d)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

1.022.021.041.933.971.980.971.00

0.97

7.217.237.247.297.317.327.357.367.387.417.437.447.457.467.477.477.487.507.537.557.607.617.627.797.807.81

12.64

NH

N

F

0102030405060708090100110120130140150160170180190200210220

126.9

127.5

127.5

128.1

128.4

128.5

129.0

130.4

130.5

130.6

131.2

131.9

131.9

135.4

137.2

143.7

NH

N

F

S24

Figure S5. 1H (top) and 13C (bottom) NMR spectra of 2-(2-fluorophenyl)-4,5-diphenyl-1H-imidazole (C21H15FN2, 1e)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

1.005.102.041.971.97

1.93

0.87

7.217.227.247.297.307.317.327.337.347.367.387.397.437.457.467.497.517.547.558.108.118.128.13

12.69

NH

N

F

0102030405060708090100110120130140150160170180190200210220

115.6

115.8

126.5

127.0

127.3

127.4

127.8

128.2

128.4

128.7

144.7

161.1

163.1

NH

N

F

S25

Figure S6. 1H (top) and 13C (bottom) NMR spectra of 2-(4-fluorophenyl)-4,5-diphenyl-1H-imidazole (C21H15FN2, 1f)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

1.871.003.342.944.92

1.02

7.467.487.497.517.597.687.757.777.817.837.857.868.248.268.298.398.40

13.50

NH

N

N+

O

O-

0102030405060708090100110120130140150160170180190200210220

122.7

124.1

126.1

126.2

126.5

127.4

127.7

128.2

128.5

128.8

129.0

129.2

130.9

131.2

131.8

132.8

136.9

159.4

183.9

NH

N

N+

O

O-

S26

Figure S7. 1H (top) and 13C (bottom) NMR spectra of 2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole (C21H15N3O2, 1g)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

0.983.398.241.071.00

0.91

7.227.237.247.297.317.327.357.367.387.427.437.457.467.477.487.487.507.537.557.607.617.627.797.807.81

12.64

NH

N

Cl

102030405060708090100110120130140150160170180190200210220

126.2

126.9

127.4

127.9

128.3

129.7

129.9

129.9

130.6

131.2

131.3

134.8

136.5

143.1

NH

N

Cl

S27

Figure S8. 1H (top) and 13C (bottom) NMR spectra of 2-(2-chlorophenyl)-4,5-diphenyl-1H-imidazole (C21H15ClN2, 1h)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

0.931.891.007.18

1.93

1.01

7.237.247.297.307.327.387.407.437.457.467.497.517.548.098.10

12.78

NH

N

Cl

0102030405060708090100110120130140150160170180190200210220

126.94

127.17

127.39

128.21

128.54

128.75

128.89

129.01

129.11

129.52

131.24

133.07

135.32

137.62

144.74

NH

N

Cl

S28

Figure S9. 1H (top) and 13C (bottom) NMR spectra of 2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazole (C21H15ClN2, 1i)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.52.97

1.911.001.961.021.962.011.991.94

0.90

7.037.057.217.237.287.297.317.367.377.427.437.457.487.507.537.558.008.02

12.51

NH

N

O

CH3

0102030405060708090100110120130140150160170180190200210220

55.2

114.1

126.7

127.0

127.6

128.1

128.3

128.6

145.6

159.4

NH

N

O

CH3

S29

Figure S10. 1H (top) and 13C (bottom) NMR spectra of 2-(4-methoxyphenyl)-4,5-diphenyl-1H-imidazole (C22H18N2O, 1k)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

6.03

2.021.001.941.042.082.082.052.03

0.95

2.96

6.786.807.207.217.277.297.307.347.357.417.427.437.477.497.537.547.897.91

12.31

N

NH

NCH3

CH3

102030405060708090100110120130140150160170180190200210220

39.9

111.9

118.3

126.3

127.0

127.4

128.1

128.3

128.6

131.4

135.5

136.5

146.5

150.3

N

NH

NCH3

CH3

S30

Figure S11. 1H (top) and 13C (bottom) NMR spectra of 4-(4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline (C23H21N3, 1l)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

9.02

1.002.061.011.993.952.111.90

1.06

1.32

7.207.227.237.297.307.317.377.387.437.447.467.497.507.547.558.008.01

12.61

NH

N CH3

CH3

CH3

0102030405060708090100110120130140150160170180190200210

31.4

34.8

125.3

125.7

126.8

127.4

128.0

128.3

128.5

128.8

129.0

131.5

135.6

137.3

145.9

151.1

NH

N CH3

CH3

CH3

S31

Figure S12. 1H (top) and 13C (bottom) NMR spectra of 2-(4-(tert-butyl)phenyl)-4,5-diphenyl-1H-imidazole (C24H22N2, 1m)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

3.07

1.004.071.152.072.071.962.02

1.02

2.35

7.227.237.287.287.297.307.317.377.387.427.447.457.497.507.547.557.977.98

12.59

NH

N

CH3

0102030405060708090100110120130140150160170180190200210220

21.2

125.5

126.8

127.4

128.0

128.2

128.5

128.7

129.0

129.6

131.5

135.6

137.2

138.0

146.0

NH

N

CH3

S32

Figure S13. 1H (top) and 13C (bottom) NMR spectra of 4,5-diphenyl-2-(p-tolyl)-1H-imidazole (C22H18N2, 1n)

0.51.52.53.54.55.56.57.07.58.59.510.511.512.513.5

3.443.423.302.082.071.071.00

1.08

1.04

7.147.167.167.187.197.217.237.317.327.347.367.377.437.457.467.517.537.637.648.008.478.48

11.37

12.27

NH

NNH

0102030405060708090100110120130140150160170180190200210220

106.5

111.3

119.4

121.2

121.5

123.4

124.7

125.4

125.8

126.5

127.1

127.8

128.3

131.3

135.4

135.6

135.9

143.4

NH

NNH

S33

Figure S14. 1H (top) and 13C (bottom) NMR spectra of 3-(4,5-diphenyl-1H-imidazol-2-yl)-1H-indole (C23H17N3, 1o)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

11.34

8.25

7.047.057.137.147.427.437.477.597.617.677.697.927.93

N

N

S34

102030405060708090100110120130140150160170180190200210220

125.6

127.0

127.8

128.3

128.3

128.5

128.6

128.6

128.7

128.9

129.4

129.5

131.0

131.1

131.3

131.5

134.9

137.6

147.3

N

N

Figure S15. 1H (top) and 13C (bottom) NMR spectra of 1,2,4,5-tetraphenyl imidazole (C27H20N2, 2a)

1.02.03.04.05.06.07.07.58.59.510.511.512.513.5

1.391.001.3116.95

1.16

6.546.556.576.666.666.676.676.936.957.297.317.317.387.387.407.437.45

N

N

OH

S35

102030405060708090100110120130140150160170180190200210220

113.9

116.9

118.1

126.1

126.8

126.9

128.4

128.5

128.6

128.7

129.3

129.4

129.6

130.2

130.8

131.3

133.2

134.4

136.6

144.4

157.3

N

N

OH

Figure S16. 1H (top) and 13C (bottom) NMR spectra of 2-(2-hydroxyphenyl)-1,4,5-triphenyl imidazole (C27H20N2O, 2b)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

2.021.1513.84

2.03

1.00

6.666.686.707.157.177.187.237.247.287.297.327.327.477.48

9.50

N

N

OH

S36

0102030405060708090100110120130140150160170180190200210220

115.4

115.4

118.9

126.3

126.4

128.2

128.4

128.4

128.7

129.1

129.1

130.4

131.2

131.2

131.5

134.4

136.7

136.7

146.1

157.0

N

N

OH

Figure S17. 1H (top) and 13C (bottom) NMR spectra of 2-(3-hydoxyphenyl)-1,4,5-triphenyl imidazole (C27H20N2O, 2c)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

1.94

17.02

1.00

6.65

7.227.307.47

9.67

N

N

OH

S37

102030405060708090100110120130140150160170180190200210220

114.9

121.2

126.3

128.1

128.3

128.4

128.5

128.8

129.1

129.8

130.6

130.6

131.1

134.6

136.4

136.9

146.4

157.6

N

N

OH

Figure S18. 1H (top) and 13C (bottom) NMR spectra of 2-(4-hydroxyphenyl)-1,4,5-triphenyl imidazole (C27H20N2O, 2d)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

1.9611.28

1.142.981.081.00

6.936.957.137.147.167.177.197.197.217.237.247.257.257.267.487.507.517.577.587.617.627.667.687.897.91

N

N

N+O

O-

S38

0102030405060708090100110120130140150160170180190200210220

124.8

127.0

127.1

127.8

128.4

128.5

128.8

129.3

130.3

130.7

131.0

131.4

133.3

133.8

134.6

136.1

139.1

143.7

149.3

N

N

N+O

O-

Figure S19. 1H (top) and 13C (bottom) NMR spectra of 2-(2-nitrophenyl)-1,4,5-triphenyl imidazole (C27H19N3O2, 2e)

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.513.013.514.0

0.501.454.501.001.031.00

7.197.217.227.277.327.357.507.527.617.638.148.16

N

N

N+

O

O-

S39

0102030405060708090100110120130140150160170180190200210220

123.5

126.4

126.8

128.3

128.5

128.6

128.7

128.8

129.2

129.5

129.9

131.1

132.8

133.9

136.2

136.3

137.8

143.8

146.7

N

N

N+

O

O-

Figure S20. 1H (top) and 13C (bottom) NMR spectra of 2-(4-nitrophenyl)-1,4,5-triphenyl imidazole (C27H19N3O2, 2f)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

2.986.206.001.982.00

7.137.147.167.187.197.237.257.267.277.277.297.307.337.347.397.407.417.427.487.49

N

N

F

S40

0102030405060708090100110120130140150160170180190200210220

115.1

115.3

126.3

128.2

128.5

128.7

131.1

145.2

160.9

162.9

N

N

F

Figure S21. 1H (top) and 13C (bottom) NMR spectra of 2-(4-florophenyl)-1,4,5-triphenyl imidazole (C27H19N2F, 2g)

1.02.03.04.05.06.07.07.58.59.510.511.512.513.5

1.0016.17

2.03

7.177.187.197.247.257.307.307.317.347.357.357.377.487.49

N

N

Cl

S41

102030405060708090100110120130140150160170180190200210220

126.8

127.0

128.7

128.8

129.0

129.0

129.2

129.4

129.7

129.7

130.3

130.7

131.6

132.1

133.6

134.7

136.9

137.5

145.4

N

N

Cl

Figure S22. 1H (top) and 13C (bottom) NMR spectra of 2-(4-chlorophenyl)-1,4,5-triphenyl imidazole (C27H19N2Cl, 2h)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

3.00

2.061.026.148.372.11

3.72

6.836.857.227.247.257.297.327.337.347.477.49

N

N

OCH3

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0102030405060708090100110120130140150160170180190200210220

55.1

113.6

126.3

128.1

128.4

128.8

129.1

129.6

131.1

146.0

159.2

N

N

OCH3

Figure S23. 1H (top) and 13C (bottom) NMR spectra of 2-(4-methoxyphenyl)-1,4,5-triphenyl imidazole (C28H22N2O, 2k)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

6.00

1.99

8.107.212.21

2.88

6.566.587.147.157.177.197.217.227.237.277.287.327.337.467.48

N

N

N CH3

CH3

S43

-20-100102030405060708090100110120130140150160170180190200210220111.3

117.7

126.2

126.3

128.1

128.2

128.4

128.5

128.8

129.0

129.1

130.4

130.7

131.2

134.7

136.3

137.1

146.7

149.9

N

N

N CH3

CH3

Figure S24. 1H (top) and 13C (bottom) NMR spectra of 2-(4-N,N-dimethylaminophenyl)-1,4,5-triphenyl imidazole (C29H25N3, 2l)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

3.195.007.061.423.14

7.317.337.377.397.407.517.527.637.647.657.837.847.887.90

N

N

O OH

S44

0102030405060708090100110120130140150160170180190200210220

127.3

127.6

128.5

128.6

128.8

129.0

130.2

130.7

132.7

144.9

169.0

N

N

O OH

Figure S25. 1H (top) and 13C (bottom) NMR spectra of 2-(2-carboxyphenyl)-1,4,5-triphenyl imidazole (C28H20N2O2, 2m)

0.51.52.53.54.55.56.57.07.58.59.510.511.512.513.5

9.03

17.31

2.00

1.24

7.157.177.187.237.247.267.287.297.317.317.347.347.357.477.49

N

N

CH3

CH3CH3

S45

0102030405060708090100110120130140150160170180190200210220

31.0

34.4

125.0

126.4

126.4

127.6

127.9

128.2

128.4

128.5

128.8

129.2

130.5

131.1

131.2

134.5

136.7

136.8

146.0

150.8

N

NCH3CH3

CH3

Figure S26. 1H (top) and 13C (bottom) NMR spectra of 2-(4-tert-butylphenyl)-1,4,5-triphenyl imidazole (C31H29N2, 2o)

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

3.00

2.159.226.102.16

2.26

7.087.107.247.257.277.297.297.327.337.487.497.49

N

N

CH3

S46

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20.7

126.3

126.4

127.6

128.1

128.2

128.4

128.4

128.7

128.7

128.8

129.1

130.5

131.1

131.1

134.5

136.7

136.7

137.8

146.1

N

N

CH3

Figure S27. 1H (top) and 13C (bottom) NMR spectra of 2-(4-methylphenyl)-1,4,5-triphenyl imidazole (C28H22N2, 2p)

0.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.511.512.513.5

3.00

1.001.041.0715.27

1.02

1.89

6.407.207.217.237.297.317.377.397.407.437.44

12.32

N

N

CH3

OH

S47

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20.1

113.4

116.7

126.1

128.4

128.5

128.7

128.7

129.3

131.3

144.6

155.1

N

N

OH

CH3

Figure S28. 1H (top) and 13C (bottom) NMR spectra of 2-(2-hydroxy-5-methylphenyl)-1,4,5-triphenyl imidazole (C28H23N2O, 2q)

S48

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