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: ptsowmya8@gmail.com 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

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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

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1H NMR of compound 4a

4

13C NMR of compound 4a

LCMS of compound 4a

5

1H NMR of compound 4b

6

13C NMR of compound 4b

LCMS of compound 4b

7

1H NMR of compound 4c

13C NMR of compound 4c

8

LCMS of compound 4c

9

1H NMR of compound 4d

13C NMR of compound 4d

10

LCMS of compound 4d

11

1H NMR of compound 4e

13C NMR of compound 4e

12

LCMS of compound 4e

13

1H NMR of compound 4f

13C NMR of compound 4f

14

LCMS of compound 4f

15

1H NMR of compound 4g

13C NMR of compound 4g

16

LCMS of compound 4g

17

1H NMR of compound 4h

13C NMR of compound 4h

18

LCMS of compound 4h

19

1H NMR of compound 4i

13C NMR of compound 4i

20

LCMS of compound 4i

21

1H NMR of compound 4j

13C NMR of compound 4j

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,-

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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-

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

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×-

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,

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%

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1H NMR of compound 3b

1H NMR of compound 3f

29

\

13C NMR of compound 3f

1H NMR of compound 3h

30

13C NMR of compound 3h

31

POM Images of triazoles

Showing smectic phase at 63.70C

POM images of compound 4j

32

Showing Nematic phase at 68.30C

POM images of compound 4f

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Showing Nematic phase at 65.00C

POM images of compound 4e

Showing Nematic phase at 58.20C

Figure S16: POM images of compound 4d

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Compound showing smectic phase at 69.80C

POM images of compound 4h

35

Figure S18: DSC spectra of compound 4d

DSC spectra of compound 4f

36

DSC spectra of compound 4g

DSC spectra of compound 4j

37

XRD images of compounds 4a and 4e

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XRD images of compounds 4g and 4j

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UV-visible of compounds of 4e, 4f, 4h and 4i