Page 1
10.1071/CH16540_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(7), 764-768
SUPPLEMENTARY MATERIAL
Synthesis and liquid crystalline properties of a new homologous series of 4,5-disubstituted
2H-[1,2,3]-triazoles via azide-chalcone oxidative cycloaddition reaction
Sowmya P T a, K M Lokanatha Rai a,*
a,*Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, Karnataka, India,
*e-mail: [email protected] Tel: +919008196715
* For correspondence
CONTENTS
1) 1H NMR of compound 4a……………………………………….…3 2) 13C NMR of compound 4a…………………………………………3 3) LCMS of compound 4a……………………………………………4 4) 1H NMR of compound 4b………………………………………….5 5) 13C NMR of compound 4b………………………………………....5 6) LCMS of compound 4b……………………………………………6 7) 1H NMR of compound 4c……………………………………..........7 8) 13C NMR of compound 4c……………………………………….....7 9) LCMS of compound 4c……………………………………………..8 10) 1H NMR of compound 4d………………………………………......9 11) 13C NMR of compound 4d…………………………………….........9 12) LCMS of compound 4d……………………………………………10 13) 1H NMR of compound 4e…………………………………………11 14) 13C NMR of compound 4e…………………………………………11 15) LCMS of compound 4e……………………………………………12 16) 1H NMR of compound 4f……………………………………........13 17) 13C NMR of compound 4f…………………………………….......13 18) LCMS of compound 4f……………………………………………14 19) 1H NMR of compound 4g……………………………………........15 20) 13C NMR of compound 4g…………………………………………15 21) LCMS of compound 4g……………………………………………16
Page 2
2
22) 1H NMR of compound 4h……………………………………........17 23) 13C NMR of compound 4h………………………………………..17 24) LCMS of compound 4h…………………………………………..18 25) 1H NMR of compound 4i…………………………………….........19 26) 13C NMR of compound 4i…………………………………………19 27) LCMS of compound 4i……………………………………………20 28) 1H NMR of compound 4j……………………………………........21 29) 13C NMR of compound 4j………………………………………...21 30) LCMS of compound 4j……………………………………………22 31) Spectral data’s of compounds 4a-4j & 3a-3j…………….…......22-27 32) 1H NMR of compound 3b…………………………………….......28 33) 1H NMR of compound 3f…………………………………….......28 34) 13C NMR of compound 3f………………………………..…........29 35) 1H NMR of compound 3h…………………………………….......29 36) 13C NMR of compound 3h………………………………..…........30 37) POM images of compound 4j…………………………………...31 38) POM images of compound 4f……………………………………32 39) POM images of compounds 4e & 4d……………………………33 40) POM images of compound 4h…………………………………...34 41) DSC spectra of compound 4d and 4f……………………………35 42) DSC spectra of compound 4g and 4j…………………………….36 43) XRD images of compounds 4a and 4e…………………………..37 44) XRD images of compounds 4g and 4j…………………………...38 45) UV-visible of compounds of 4e, 4f, 4h and 4i……………………39
Page 3
3
1H NMR of compound 4a
Page 4
4
13C NMR of compound 4a
LCMS of compound 4a
Page 5
5
1H NMR of compound 4b
Page 6
6
13C NMR of compound 4b
LCMS of compound 4b
Page 7
7
1H NMR of compound 4c
13C NMR of compound 4c
Page 8
8
LCMS of compound 4c
Page 9
9
1H NMR of compound 4d
13C NMR of compound 4d
Page 10
10
LCMS of compound 4d
Page 11
11
1H NMR of compound 4e
13C NMR of compound 4e
Page 12
12
LCMS of compound 4e
Page 13
13
1H NMR of compound 4f
13C NMR of compound 4f
Page 14
14
LCMS of compound 4f
Page 15
15
1H NMR of compound 4g
13C NMR of compound 4g
Page 16
16
LCMS of compound 4g
Page 17
17
1H NMR of compound 4h
13C NMR of compound 4h
Page 18
18
LCMS of compound 4h
Page 19
19
1H NMR of compound 4i
13C NMR of compound 4i
Page 20
20
LCMS of compound 4i
Page 21
21
1H NMR of compound 4j
13C NMR of compound 4j
Page 22
22
LCMS of compound 4j
Analytical data’s of compounds 4a-4j
(5-(4-butoxy-3-methoxyphenyl)-2H-1,2,3-triazol-4-yl)(4-butoxyphenyl)methanone (4a): 1H NMR (CDCl3, 400 MHz) δ: 0.98(t, -CH3, 6H), 1.81(m, -CH2, 9H), 3.79(s, -OCH3, 3H), 3.95(t,
2×OCH2, 4H), 6.82(d, J=8.4 Hz, ArH, 1H), 6.89(d, J=8.4 Hz, ArH, 2H), 7.29(d, J=7.6 Hz, ArH, 1
H), 7.37(s, ArH, 1H), 8.04(d, J=8.4 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz) δ: 10.3, 22.3, 29.
6 (aliphatic), 56.0 (-OCH3), 69.5, 69.7 (-OCH2), 112.4, 114.1, 120.6, 121.6, 129.8, 132.9, 140.8
(aromatic), 145.5, 149.1 (1,2,3-triazole), 163.6; 186.8 (carbonyl). LCMS: 424.25 [M+H]+.
Elemental Analysis (%): Calcd for C24H29N3O4 C 68.06 H 6.90 N 9.92; found C 68.02 H 6.93 N
9.89. Yield: 86%.
(5-(3-methoxy-4-(pentyloxy)phenyl)-2H-1,2,3-triazol-4-yl)(4-(pentyloxy)phenyl)methanone (4b): 1H
NMR (CDCl3, 400 MHz) δ: 0.92(t, -CH3, 6H), 1.34(m, -CH2, 8H), 1.79(m,-CH2, 4H), 3.83(s, -
OCH3,3H), 4.01(t, -OCH2, 4H), 6.86(d, J=8.4 Hz, ArH, 1H), 6.90(d, J=8.8 Hz, ArH, 2H), 7.33(d, J=8.4
Hz, ArH, 1H), 7.39(s, ArH, 1H), 8.04(d, J=8.8 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz) δ: 13.9, 14.0,
22.5, 22.6, 25.5, 28.9, 29.0, 31.5 (aliphatic), 55.9 (-OCH3), 68.3, 69.0 (-OCH2), 112.3, 114.1, 120.5, 121.6,
129.8, 132.9, 140.8 (aromatic), 145.3, 149.6 (1,2,3-triazole), 163.6; 186.8 (carbonyl). LCMS:
452.23 [M+H]+. Elemental Analysis (%): Calcd for C26H33N3O4 C 69.16 H 7.37 N 9.31; found C 69.10 H
7.34 N 9.29. Yield: 85%.
(5-(4-(hexyloxy)-3-methoxyphenyl)-2H-1,2,3-triazol-4-yl)(4-(hexyloxy)phenyl)methanone (4c):
1H NMR (DMSO-d6, 400 MHz) δ: 0.85(t, -CH3, 6H), 1.07(m, -CH2, 2H), 1.28(m,-CH2, 6H), 1.38(m,-
Page 23
23
CH2, 4H), 1.70(m,-CH2, 4H), 3.72(s, -OCH3, 3H), 4.02(t, 2×-OCH2, 4H) 6.98(d, J=8.8 Hz, ArH, 1H),
7.03 (d, J=8.8 Hz, ArH, 2H),7.28(d, J=8 Hz, ArH, 1H), 7.35(s, ArH, 1H), 7.96(d, J=7.2 Hz,ArH, 2H),
15.69(br s, N-H). 13C NMR (DMSO-d6, 100 MHz) δ: 13.9, 14.0, 22.6, 25.5, 28.9, 29.0, 29.3, 29.6, 31.4,
31.8 (aliphatic), 55.9 (-OCH3), 68.3, 69.0 (-OCH2), 112.4, 114.1, 120.5, 121.64, 132.9, 140.8 (aromatic),
145.3, 149.6 (1,2,3 -triazole), 163.6; 186.8 (carbonyl). LCMS: 480.24 [M+H]+. Elemental Analysis (%):
Calcd for C28H37N3O4 C 70.12 H 7.78 N 8.76; found C 70.10 H 7.69 N 8.74. Yield: 82%.
(5-(4-(heptyloxy)-3-methoxyphenyl)-2H-1,2,3-triazol-4-yl)(4-(heptyloxy)phenyl)methanone
(4d): 1H NMR (DMSO-d6, 400 MHz) δ: 0.84(t, -CH3, 6H), 1.23(m, -CH2, 16H), 1.68(m,-CH2, 4H),
3.72(s, -OCH3, 3H), 4.02(t, 2×-OCH2, 4H), 6.98(d, J=8.4 Hz, ArH, 1H), 7.03(d, J=8.8 Hz, ArH, 2H),
7.28(d, J=8 Hz, ArH, 1H), 7.35(s, ArH,1H), 7.94(d, J=8 Hz, ArH, 2H), 15.70(br s, N-H). 13C NMR
(DMSO-d6, 100 MHz) δ:14.0, 22.5, 22.6, 25.8, 28.9, 29.0, 29.3, 29.4, 29.6, 30.1, 31.3, 31.8
(aliphatic), 55.9 (-OCH3), 68.3, 69.0 (-OCH2) 112.3, 112.4, 114.0, 121.6, 129.8, 132.92 (aromatic),
149.0, 149.6 (1,2,3-triazole), 163.5; 186.8 (carbonyl). LCMS: 508.26 [M+H]+.
Elemental Analysis (%): Calcd for C30H41N3O4 C 70.98 H 8.14 N 8.28; found C 70.88 H 8.12 N 8.27.
Yield: 82%.
(5-(3-methoxy-4-(octyloxy)phenyl)-2H-1,2,3-triazol-4-yl)(4-(octyloxy)phenyl)methanone (4e): 1H NMR (CDCl3, 400 MHz) δ: 0.87(t, -CH3, 6H), 1.29(m, -CH2, 16H), 1.44(m,-CH2, 4H) 1.81(m, -
CH2, 4H), 3.85(s, CH3, 3H), 4.02(t, 2×-OCH2, 4H), 6.86(d, J=8 Hz, ArH, 1H),6.92 (d, J=9.2 Hz, ArH,
2H),7.34(d, J=8 Hz, ArH, 1H), 7.40 (s, ArH, 1H), 8.05(d, J=8.8 Hz, ArH, 2H), 12.00 (br s, N-H, 1H). 13C NMR (CDCl3, 100 MHz) δ: 14.0, 22.6, 25.8, 25.8, 28.9, 29.0, 29.2, 29.2, 29.3, 29.4, 29.6, 29.6, 30.
1,31.3, 31.7, 31.8 (aliphatic), 55.9 (-OCH3), 68.3, 69.0 (-OCH2), 112.3, 112.4, 114.0, 120.5, 121.6,
129.8, 132.9 (aromatic), 149.0, 149.6 (1,2,3-triazole), 163.5; 186.8 (carbonyl). LCMS: 536.31
[M+H]+. Elemental Analysis (%): Calcd for C32H45N3O4 C 71.74 H 8.47 N 7.84; found C 71.73 H 8.44
N 7.82. Yield: 81%.
(5-(4-(decyloxy)-3-methoxyphenyl)-2H-1,2,3-triazol-4-yl)(4-(decyloxy)phenyl)methanone (4f): 1H NMR (CDCl3, 400 MHz) δ: 0.87(t, -CH3, 6H), 1.29(m, -CH2, 24H), 1.44(m,-CH2, 4H) 1.81(m, -CH2,
4H), 3.85(s, CH3, 3H), 4.02(t, 2×-OCH2, 4H), 6.86(d, J=8 Hz, ArH, 1H), 6.92 (d, J=9.2 Hz, ArH, 2H),
7.34(d, J=8 Hz, ArH, 1H), 7.40 (s, ArH, 1H), 8.05(d, J=8.8 Hz, ArH, 2H), 12.00 (br s, N-H, 1H). 13C NMR (CDCl3, 100 MHz) δ: 14.0, 22.6, 25.8, 25.9, 29.0, 29.1, 29.3, 29.3, 29.6, 31.7 (aliphatic), 56.0 (-
OCH3), 68.3, 69.0 (-OCH2), 112.3, 112.5, 114.1, 121.5, 129.8, 132.9 (aromatic), 149.1, 149.6 (1,2,3-
Page 24
24
triazole), 163.6; 186.7 (carbonyl). LCMS: 592.62 [M+H]+. Elemental Analysis (%): Calcd for C36H53N3
O4 C 73.06 H 9.03 N 7.10; found C 73.0 H 9.01 N 7.05. Yield: 80%.
(5-(4-(dodecyloxy)-3-methoxyphenyl)-2H-1,2,3-triazol-4-yl)(4-(dodecyloxy)phenyl)methanone (4g): 1H NMR (CDCl3, 400 MHz) δ: 0.86(t, -CH3, 6H), 1.25(m, -CH2, 32H), 1.44(m,-CH2, 4H), 1.81(m,-
CH2, 4H), 3.85(s, -OCH3, 3H), 4.02(t, 2×-OCH2, 4H), 6.88(d, J=8.4 Hz, ArH, 1H), 6.92(d, J=9.2 Hz,
ArH, 2H),7.32(d, ArH, 1H), 7.40(s, ArH, 1H), 8.05(d, J=8.8 Hz, ArH, 2H). 13C NMR(CDCl3,100 MHz)
δ: 14.0, 22.6, 25.8, 25.9, 29.0, 29.1, 29.3, 29.3, 29.6, 31.7 (aliphatic), 56.0(-OCH3), 68.3, 69.0(-OCH2)
,12.3, 112.5, 114.1, 121.5, 129.8, 132.9 (aromatic), 149.1, 149.6 (1,2,3-triazole), 163.5;186.7
(carbonyl). LCMS: 648.43 [M+H]+. Elemental Analysis (%): Calcd for C40H61N3O4 C 74.15 H 9.49
N 6.49; found C 74.10 H 9.46 N 6.44. Yield: 78%.
(5-(3-methoxy-4-(tetradecyloxy)phenyl)-2H-1,2,3-triazol-4-yl)(4-(tetradecyloxy)phenyl)methanone
(4h): 1H NMR (CDCl3, 400 MHz) δ: 0.86(t, -CH3, 6H), 1.25(m, -CH2, 40H), 1.43(m,-CH2, 4H), 1.80(m,-
CH2, 4H), 3.85(s, -OCH3, 3H), 4.02(t, 2×-OCH2, 4H), 6.87(d, J=8.8 Hz, ArH, 1H), 6.92(d, J=8.4 Hz,
ArH, 2H),7.32(d, J=6.4 Hz, ArH, 1H), 7.40(s, ArH, 1H), 8.05(d, J=8.8 Hz, ArH, 2H). 13C NMR
(CDCl3,100 MHz) δ: 14.0, 22.6, 25.9, 29.0, 29.3, 29.5, 29.6, 31.8 (aliphatic), 56.0 (-OCH3), 68.3, 69.0 (-
OCH2), 112.4, 112.5, 114.1, 120.7, 121.5, 132.9 (aromatic), 149.1, 149.6 (1,2,3-triazole), 163.6; 186.6
(carbonyl). LCMS: 704.53 [M+H]+. Elemental Analysis: Calculated for C44H69N3O4 C 75.06 H 9.88
N 5.97; found C 75.02 H 9.85 N 5.94. Yield: 78%.
(5-(4-(hexadecyloxy)-3-methoxyphenyl)-2H-1,2,3-triazol-4-yl)(4-(hexadecyloxy)phenyl)methanone
(4i) 1H NMR (CDCl3, 400 MHz) δ: 0.87(t,CH3, 6H), 1.27(m, -CH2, 48H), 1.75(m,-CH2, 4H) 1.83(m, -
CH2, 4H), 3.85(s, CH3, 3H), 4.01(t, 2×-OCH2, 4H), 6.88(d, J=8 Hz, ArH, 1H), 6.92 (d, J=9.2 Hz, ArH,
2H), 7.32(d, J=8 Hz, ArH, 1H), 7.40 (s, ArH, 1H), 8.05(d, J=8.8 Hz, ArH, 2H), 11.92 (br s, N-H, 1H). 13C NMR (CDCl3, 100 MHz) δ: 14.0, 22.6, 25.9, 29.0, 29.3, 29.5, 29.6, 31.8 (aliphatic), 56.0 (-OCH3),
68.3, 69.0 (-OCH2), 112.4, 112.5, 114.1, 120.6, 121.5, 129.8, 132.9 (aromatic), 149.1, 149.7 (1,2,3-
triazole), 163.6; 186.6 (carbonyl). LCMS: 760.31 [M+H]+. Elemental Analysis(%): Calcd for C48H77N3O4
C 75.84 H 10.21 N 5.53; found C 75.79 H 10.18 N 5.50. Yield: 77%.
(5-(3-methoxy-4-(octadecyloxy)phenyl)-2H-1,2,3-triazol-4-yl)(4-(octadecyloxy)phenyl)methanone
(4j): 1H NMR (CDCl3, 400 MHz) δ: 0.86(t,CH3, 6H), 1.28(m, -CH2, 60H), 1.80(m,-CH2, 4H), 3.85(s,
CH3, 3H), 4.01(t, 2×-OCH2, 4H), 6.89(d, J=8 Hz, ArH, 1H), 6.91(d, J=8.8 Hz, ArH, 2H), 7.33(d, J=6.4
Page 25
25
Hz,ArH,1H),7.39 (s, ArH, 1H), 8.05(d, J=8.8 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz) δ: 14.0, 22.6, 2
5.9, 29.0, 29.3, 29.5, 29.6, 31.8 (aliphatic), 56.0 (-OCH3), 68.3, 69.0 (-OCH2), 112.4, 112.5, 114.1, 120.6,
121.5, 129.8, 132.9 (aromatic), 149.1, 149.7 (1,2,3-triazole), 163.6; 186.6 (carbonyl). LCMS: 816.43
[M+H]+. Elemental Analysis (%): Calcd for C52H85N3O4 C 77.91 H 10.64 N 5.34; found C 77.89 H 10.62
N 5.31 Yield: 77%.
Spectral data’s for compounds 3a-3j
3-(4-butoxy-3-methoxyphenyl)-1-(4-butoxyphenyl)prop-2-en-1-one (3a): 1H NMR (CDCl3, 400 MHz)
δ: 0.89(t, -CH3, 6H), 1.31 (m,-CH2, 9H), 3.92(s, -OCH3, 3H), 4.06(t, 2×-OCH2, 4H), 6.87 (d, J=8.4
Hz, ArH, 1H), 6.95(d, J=7.2 Hz, ArH, 2H), 7.18(s, ArH, 1H), 7.20(d, J=8 Hz, ArH, 1H), 7.42 (d, J=13.6
Hz, α-H, chalcone), 7.75(d, J=15.2 Hz, β-H, chalcone), 8.02(d, J=8.4 Hz ArH, 2H). 13C NMR (CDCl3,
100 MHz) δ:10.3, 10.4, 14.0, 22.3, 22.4, 25.9, 29.1, 29.2, 31.7, 56.0,68.1, 70.4, 110.6, 110.8, 112.4,
114.2,114.2, 119.6,119.8, 122.8, 122.9, 127.9, 130.6, 130.7, 131.1,144.1, 144.1,149.5, 150.9, 162.9,
188.7.Yield: 87%.
3-(3-methoxy-4-(pentyloxy) phenyl)-1-(4-(pentyloxy) phenyl) prop-2-en-1-one (3b): 1H NMR (CDCl3,
400 MHz) δ: 0.86 (t, -CH3, 6H), 1.31 (m,-CH2, 8H), 1.29(m, -CH2, 4H), 3.92(s, -OCH3, 3H), 4.02(t, 2×-
OCH2, 4H), 6.86 (d, J=8.4 Hz, ArH, 1H), 6.92(d, J=7.2 Hz, ArH, 2H), 7.15(s, ArH, 1H), 7.22(d, J=8
Hz, ArH, 1H), 7.42 (d, J=13.6 Hz, α-H, chalcone), 7.75(d, J=15.2 β-H, chalcone), 8.01(d, J=8.4 Hz, ArH,
2H).13C NMR (CDCl3, 100 MHz) δ:10.3, 10.4, 14.0, 22.3, 22.4, 25.9, 29.1, 31.7, 56.0, 56.2, 68.1, 70.7, 1
10.6, 110.8, 112.4, 114.2, 119.8, 122.9, 127.9, 130.6, 130.7, 131.1,144.0, 144.1,149.5,150.9, 162.9, 188.7
Yield: 87%.
3-(4-(hexyloxy)-3-methoxyphenyl)-1-(4-(hexyloxy)phenyl)prop-2-en-1-one (3c): 1H NMR (CDCl3, 400
MHz) δ: 0.89 (t, -CH3,6), 1.31 (m,-CH2, 8H), 1.29(m, -CH2, 4H), 1.39 (m,-CH2, 4H), 3.92(s, -OCH3, 3H),
4.06(t, 2×-OCH2, 4H), 6.86 (d, J=8.4 Hz, ArH, 1H), 6.92(d, J=7.2 Hz, ArH, 2H), 7.15(s, ArH, 1H),
7.22(d, J=8Hz, ArH, 1H), 7.42 (d, J=13.6 Hz, α-H, chalcone), 7.75(d, β-H, chalcone), 8.01(d, J=8.4 Hz,
ArH, 2H). 13C NMR (CDCl3, 100 MHz) δ: 14.1,14.0, 22.3, 22.4, 25.9, 29.1, 29.1, 29.2, 31.7, 56.0, 56.2,
68.1, 68.2, 70.4, 76.6, 76.9, 77.3, 110.6, 110.8, 112.9, 114.2, 114.2, 119.6, 119.8, 122.8, 122.9, 127.9, 13
0.6, 130.7, 131.1, 144.0, 144.1, 149.5, 150.9, 162.3, 188.7. Yield: 85%
3-(4-(heptyloxy)-3-methoxyphenyl)-1-(4-(heptyloxy)phenyl)prop-2-en-1-one (3d): 1H NMR (CDCl3,
400 MHz) δ: 0.89 (t, -CH3, 6H), 1.31 (m,-CH2, 16H), 1.29(m, -CH2, 4H), 3.92(s, -OCH3, 3H), 4.02(t, 2×-
Page 26
26
OCH2, 4H), 6.85 (d, J=8.4 Hz, ArH, 1H), 6.91(d, J=7.2 Hz, ArH, 2H), 7.15(s, ArH, 1H), 7.22(d, J=8Hz,
ArH, 1H), 7.42 (d, J=13.6 Hz, α-H, chalcone), 7.75(d, J=15.2 β-H, chalcone), 8.01(d, J=8.4 Hz, ArH,
2H). 13C NMR (CDCl3, 100 MHz)δ: 14.0, 22.3, 22.4, 25.9, 29.1, 29.1, 29.2, 31.7, 56.0, 56.2, 68.1, 68.2,
70.4, 110.7,110.0, 112.4, 114.0, 114.2, 119.6, 119.8,122.2,122.6,127.0, 130.6, 130.7, 131.1, 144.0, 144.6,
149.5, 150.3, 162.0, 188.7. Yield: 84%
3-(3-methoxy-4-(octyloxy)phenyl)-1-(4-(octyloxy)phenyl)prop-2-en-1-one (3e): 1H NMR (CDCl3, 400
MHz) δ: 0.89 (t, -CH3, 6H), 1.31 (m,-CH2, 16H), 1.39 (m,-CH2, 4H), 1.88 (m, -CH2, 4H), 3.92(s, -OCH3,
3H), 4.06(t, 2×-OCH2, 4H), 6.83 (d, J=8.4 Hz, ArH, 1H), 6.92(d, J=7.2 Hz, ArH, 2H), 7.15(s, ArH, 1H),
7.22(d, J=8Hz, ArH, 1H), 7.42 (d, J=13.4 Hz, α-H, chalcone), 7.75(d, J=15.1 β-H, chalcone), 8.01(d,
J=8.4 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz)δ: 14.0, 22.3, 22.4, 25.9, 29.1, 29.1, 29.2, 31.7, 56.0, 56
.2, 68.1, 68.2, 70.4, 110.7,110.0, 112.4, 114.0, 114.2, 119.6, 119.8,122.2,122.6,127.0, 130.6, 130.7, 131.1
, 144.0, 144.6,149.5, 150.3, 162.0, 188.7. Yield: 80%
3-(4-(decyloxy)-3-methoxyphenyl)-1-(4-(decyloxy)phenyl)prop-2-en-1-one (3f): 1H NMR (CDCl3, 400
MHz) δ: 0.89 (t, -CH3, 6H), 1.31 (m,-CH2, 24H), 1.39 (m,-CH2, 4H), 1.88 (m, -CH2, 4H), 3.92(s, -OCH3,
3H), 4.06(t, 2×-OCH2, 4H), 6.86 (d, J=8.4 Hz, ArH, 1H), 6.99(d, J=7.2 Hz, ArH, 2H), 7.15(s, ArH, 1H),
7.20(d, J=8Hz, ArH, 1H), 7.42 (d, J=13.4 Hz, α-H, chalcone), 7.75(d, J=15.2 β-H, chalcone), 8.02(d,
J=8.4 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz)δ: 14.0, 14.2, 22.6, 25.9, 29.0, 29.1, 29.3, 29.5, 29.6,
31.7, 56.0, 56.1, 68.2, 69.0, 70.4, 110.6,110.7, 112.4, 114.2, 114.2,122.7, 130.6, 130.7, 131.1, 144.0, 149.
5, 150.9, 162.0, 188.7. Yield: 83%
3-(4-(dodecyloxy)-3-methoxyphenyl)-1-(4-(dodecyloxy)phenyl)prop-2-en-1-one (3g): 1H NMR (CDCl3, 400
MHz) δ: 0.89 (t, -CH3, 6H), 1.31 (m,-CH2, 32H), 1.36 (m,-CH2, 4H), 1.88 (m, -CH2, 4H), 3.92(s, -OCH3,
3H), 4.06(t, 2×-OCH2, 4H), 6.86 (d, J=8.4 Hz, ArH, 1H), 6.93(d, J=7.2 Hz, ArH, 2H), 7.15(s, ArH, 1H),
7.20(d, J=8Hz, ArH, 1H), 7.42 (d, J=13.4 Hz, α-H, chalcone), 7.75(d, J=15.2 β-H, chalcone), 8.02(d,
J=8.4 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz)δ: 14.0, 14.1,22.6, 25.9, 29.0, 29.1, 29.3, 29.5, 29.6, 31.
7, 56.0, 56.1, 68.2, 69.0, 70.4, 110.6,110.7, 112.4, 114.2, 114.2,122.7, 130.6, 130.7, 131.1, 144.0, 149.5,
150.9, 162.0, 188.6. Yield: 81%
3-(3-methoxy-4-(tetradecyloxy)phenyl)-1-(4-(tetradecyloxy)phenyl)prop-2-en-1-one (3h): 1H NMR (CDCl3,
400 MHz) δ: 0.89 (t, -CH3, 6H), 1.31 (m,-CH2, 40H), 1.36 (m,-CH2, 4H), 1.88 (m, -CH2, 4H), 3.92(s, -
OCH3, 3H), 4.06(t, 2×-OCH2, 4H), 6.86 (d, J=8.4 Hz, ArH, 1H), 6.93(d, J=7.2 Hz, ArH, 2H), 7.15(s,
Page 27
27
ArH, 1H), 7.20(d, J=8Hz, ArH, 1H), 7.42 (d, J=13.4 Hz, α-H, chalcone), 7.75(d, J=15.2 β-H, chalcone),
8.02(d, J=8.4 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz)δ: 14.0, 22.6, 25.9, 29.0, 29.1, 29.3, 29.5, 29.6,
31.7, 56.0, 56.1, 68.2, 69.0, 70.4, 110.6,110.7, 112.4, 114.2, 114.2,122.7, 130.6, 130.7, 131.1, 144.0,
149.5, 150.9, 162.0, 188.7. Yield: 80%
3-(4-(hexadecyloxy)-3-methoxyphenyl)-1-(4-(hexadecyloxy)phenyl)prop-2-en-1-one (3i): 1H NMR (CDCl3, 400
MHz) δ: 0.89 (t, -CH3, 6H), 1.31 (m,-CH2, 48H), 1.36 (m,-CH2, 4H), 1.88 (m, -CH2, 4H), 3.92(s, -
OCH3, 3H), 4.06(t, 2×-OCH2, 4H), 6.86 (d, J=8.4 Hz, ArH, 1H), 6.93(d, J=7.2 Hz, ArH, 2H), 7.15(s,
ArH, 1H), 7.20(d, J=8Hz, ArH, 1H), 7.42 (d, J=13.4 Hz, α-H, chalcone), 7.75(d, J=15.3 β-H, chalcone),
8.02(d, J=8.4 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz)δ: 14.0, 22.6, 25.9, 29.0, 29.1, 29.3, 29.5, 29.6,
31.7, 56.0, 56.1, 68.2, 69.0, 70.4, 110.6,110.7, 112.4, 114.2, 114.2,122.7, 130.6, 130.7, 131.1, 144.0,
149.5, 150.9, 162.0, 188.7. Yield: 78%
3-(3-methoxy-4-(octadecyloxy)phenyl)-1-(4-(octadecyloxy)phenyl)prop-2-en-1-one (3j): 1H NMR (CDCl3,
400 MHz) δ: 0.89 (t, -CH3, 6H), 1.31 (m,-CH2, 60H), 1.36 (m,-CH2, 4H), 1.88 (m, -CH2, 4H), 3.92(s, -
OCH3, 3H), 4.06(t, 2×-OCH2, 4H), 6.86 (d, J=8.4 Hz, ArH, 1H), 6.93(d, J=7.2 Hz, ArH, 2H), 7.15(s,
ArH, 1H), 7.20(d, J=8Hz, ArH, 1H), 7.42 (d, J=13.4 Hz, α-H, chalcone), 7.75(d, J=15.3 β-H, chalcone),
8.02(d, J=8.4 Hz, ArH, 2H). 13C NMR (CDCl3, 100 MHz)δ: 14.0, 22.6, 25.9, 29.0, 29.1, 29.3, 29.5, 29.6,
31.7, 56.0, 56.1, 68.2, 69.0, 70.4, 110.6,110.7, 112.4, 114.2, 114.2,122.7, 130.6, 130.7, 131.1, 144.0,
149.5, 150.9, 162.0, 188.7. Yield: 78%
Page 28
28
1H NMR of compound 3b
1H NMR of compound 3f
Page 29
29
\
13C NMR of compound 3f
1H NMR of compound 3h
Page 30
30
13C NMR of compound 3h
Page 31
31
POM Images of triazoles
Showing smectic phase at 63.70C
POM images of compound 4j
Page 32
32
Showing Nematic phase at 68.30C
POM images of compound 4f
Page 33
33
Showing Nematic phase at 65.00C
POM images of compound 4e
Showing Nematic phase at 58.20C
Figure S16: POM images of compound 4d
Page 34
34
Compound showing smectic phase at 69.80C
POM images of compound 4h
Page 35
35
Figure S18: DSC spectra of compound 4d
DSC spectra of compound 4f
Page 36
36
DSC spectra of compound 4g
DSC spectra of compound 4j
Page 37
37
XRD images of compounds 4a and 4e
Page 38
38
XRD images of compounds 4g and 4j
Page 39
39
UV-visible of compounds of 4e, 4f, 4h and 4i