Symmetrical trimeric star-shaped mesogens based on 1,3,5-trisubstituted benzene
851
PSB-CL-5: Yield: 42% White precipitate. Elemental J = 8.5 Hz, Ar), 7.47 (d, 6H, J = 8.5 Hz, Ar), 7.81 (d,
analysis: found, C 70.44, H 5.87, N 4.05; calculated 6H, J = 8.5 Hz, Ar), 8.33 (s, 3H, CH=N). 13C-NMR
(C60H60N3O6Cl3), C 70.27, H 5.90, N 4.10. IR (KBr) (CDCl3) δ/ppm: 25.90, 25.98 (Caliphatic), 67.47, 67.67
v/cm−1: 2946, 2869 (C-H aliphatic), 1619 (C=N), 1571, (Carom-OCH2), 94.02, 114.76, 122.60, 128.95, 130.65,
1603 (C=C), 1250 (C-O ether). 1H-NMR (CDCl3) 132.14 (Carom), 118.86 (Carom-Br), 151.33 (Carom-N),
δ/ppm: 1.65–1.72 (m, 6H, CH2), 1.83–1.92 (m, 12H, 160.00 (C=N), 160.85, 161.91 (Carom-O).
CH2), 3.97 (t, 6H, J = 6.0 Hz, OCH2), 4.07 (t, 6H, J
= 6.0 Hz, OCH2), 6.10 (s, 3H, Ar), 6.90 (d, 6H, J =
8.7 Hz, Ar), 7.17 (d, 6H, J = 8.4 Hz, Ar), 7.36 (d, 6H, J
= 8.7 Hz, Ar), 7.87 (d, 6H, J = 8.4 Hz, Ar), 8.37 (s, 3H,
CH=N). 13C-NMR (CDCl3) δ/ppm: 22.72, 28.82, 28.98
(Caliphatic), 67.70, 68.18 (Carom-OCH2), 93.23, 114.76,
PSB-BR-5: Yield: 41% Beige precipitate. Elemental
analysis: found, C 62.10, H 5.31, N 3.66; calculated
(C60H60N3O6Br3), C 62.19, H 5.22, N 3.63. IR (KBr)
v/cm−1: 2941, 2868 (C-H aliphatic), 1621 (C=N), 1572,
1603 (C=C), 1251 (C-O ether). 1H-NMR (CDCl3)
δ/ppm: 1.61–1.67 (m, 6H, CH2), 1.82–1.91 (m, 12H,
CH2), 3.95 (t, 6H, J = 6.3 Hz, OCH2), 4.05 (t, 6H, J
= 6.3 Hz, OCH2), 6.08 (s, 3H, Ar), 6.96 (d, 6H, J =
8.7 Hz, Ar), 7.06 (d, 6H, J = 8.7 Hz, Ar), 7.48 (d, 6H, J
122.21, 129.12, 129.27, 131.20 (Carom), 131.99 (Carom
-
Cl), 144.92 (Carom-N), 160.08 (C=N), 160.90, 161.14
(Carom-O).
PSB-CL-6: Yield: 41% Beige precipitate. Elemental = 8.7 Hz, Ar), 7.81 (d, 6H, J = 8.7 Hz, Ar), 8.33 (s, 3H,
analysis: found, C 71.05, H 6.58, N 4.02; calculated CH=N). 13C-NMR (CDCl3) δ/ppm: 22.75, 28.91, 28.98
(C63H66N3O6Cl3), C 70.88, H 6.23, N 3.94. IR (KBr) (Caliphatic), 67.76, 67.99 (Carom-OCH2), 93.99, 114.76,
v/cm−1: 2939, 2858 (C-H aliphatic), 1620 (C=N), 1573, 122.58, 128.89, 130.63, 132.13 (Carom), 151.35 (Carom
-
1604 (C=C), 1251 (C-O ether). 1H-NMR (CDCl3) N), 118.83 (Carom-Br) 160.02 (C=N), 160.92, 161.99
δ/ppm: 1.55–1.59 (m, 12H, CH2), 1.81–1.88 (m, 12H, (Carom-O).
CH2), 3.95 (t, 6H, J = 6.3 Hz, OCH2), 4.06 (t, 6H, J
= 6.3 Hz, OCH2), 6.10 (s, 3H, Ar), 6.99 (d, 6H, J =
8.7 Hz, Ar), 7.15 (d, 6H, J = 8.7 Hz, Ar), 7.35 (d, 6H, J
= 8.7 Hz, Ar), 7.85 (d, 6H, J = 8.7 Hz, Ar), 8.36 (s, 3H,
CH=N). 13C-NMR (CDCl3) δ/ppm: 26.22, 26.29, 29.50,
29.57 (Caliphatic), 68.21, 68.46 (Carom-OCH2), 94.26,
PSB-BR-6: Yield: 38% Beige precipitate. Elemental
analysis: found, C 63.45, H 5.57, N 3.61; calculated
(C63H66N3O6Br3), C 63.01, H 5.54, N 3.50. IR (KBr)
v/cm−1: 2940, 2866 (C-H aliphatic), 1620 (C=N), 1572,
1605 (C=C), 1250 (C-O ether). 1H-NMR (CDCl3)
δ/ppm: 1.56–1.60 (m, 12H, CH2), 1.82–1.91 (m, 12H,
CH2), 3.95 (t, 6H, J = 6.3 Hz, OCH2), 4.05 (t, 6H, J
= 6.3 Hz, OCH2), 6.09 (s, 3H, Ar), 6.98 (d, 6H, J =
8.7 Hz, Ar), 7.08 (d, 6H, J = 8.7 Hz, Ar), 7.50 (d, 6H, J
115.15, 123.53, 129.58, 131.07 (Carom), 131.42 (Carom
-
Cl), 151.14 (Carom-N), 160.40 (C=N), 161.35, 162.46
(Carom-O).
PSB-BR-3: Yield: 38% Beige precipitate. Elemental = 8.7 Hz, Ar), 7.83 (d, 6H, J = 9.0 Hz, Ar), 8.36 (s, 3H,
analysis: found, C 60.52, H 4.61, N 3.95; calculated CH=N). 13C-NMR (CDCl3) δ/ppm: 29.57, 29.50, 26.29,
(C54H48N3O6Br3), C 60.35, H 4.50, N 3.91. IR (KBr) 26.22 (Caliphatic), 68.21, 68.46 (Carom-OCH2), 94.16,
v/cm−1: 2942, 2868 (C-H aliphatic), 1620 (C=N), 1571, 115.16, 123.01, 130.22, 131.09, 132.53, (Carom), 119.25
1603 (C=C), 1250 (C-O ether). 1H-NMR (CDCl3) (Carom-Br), 151.64 (Carom-N), 160.45 (C=N), 161.35,
δ/ppm: 2.23–2.31 (m, 6H, CH2), 4.12 (t, 6H, J = 6.0 Hz, 162.47 (Carom-O).
OCH2), 4.21 (t, 6H, J = 6.0 Hz, OCH2), 6.12 (s, 3H,
Ar), 6.97 (d, 6H, J = 8.7 Hz, Ar), 7.06 (d, 6H, J =
8.7 Hz, Ar), 7.48 (d, 6H, J = 8.4 Hz, Ar), 7.81 (d,
2.7 Synthesis of 1,3,5-tris{4-[(4-substituted-
phenyl)diazenyl]phenoxy}-n-alkyloxy benzene,
PAZ-X-n (X = Cl, Br ; n = 3,4,5,6)
6H, J = 8.7 Hz, Ar), 8.33 (s, 3H, CH=N). 13C-NMR
(CDCl3) δ/ppm: 29.20 (Caliphatic), 64.40, 64.66 (Carom
-
OCH2), 94.26, 114.78, 122.58, 129.10, 130.64, 132.14
(Carom), 118.04 (Carom-Br), 151.31 (Carom-N), 159.92
(C=N), 160.76, 161.75 (Carom-O).
The star-shaped mesogens PAZ-X-n were synthesized
by employing the similar procedure as mentioned in
PSB-BR-4: Yield: 43% Beige precipitate. Elemental Section 2.6.
analysis: found, C 61.40, H 4.85, N 3.80; calculated PAZ-CL-3: Yield: 37% Yellow precipitate. Elemen-
(C57H54N3O6Br3), C 61.30, H 4.87, N 3.76. IR (KBr)
v/cm−1: 2944, 2873 (C-H aliphatic), 1623 (C=N), 1572,
1603 (C=C), 1252 (C-O ether). 1H-NMR (CDCl3)
δ/ppm: 1.98–2.03 (m, 12H, CH2), 3.99 (t, 6H, J =
6.0 Hz, OCH2), 4.09 (t, 6H, J = 6.0 Hz, OCH2), 6.08
(s, 3H, Ar), 6.96 (d, 6H, J = 8.5 Hz, Ar), 7.06 (d, 6H,
tal analysis: found, C 64.96, H 4.82, N 8.91; cal-
culated (C51H45N6O6Cl3), C 64.87, H 4.80, N 8.90.
IR (KBr) v/cm−1: 2952, 2873 (C-H aliphatic), 1588,
1600 (C=C), 1473 (N=N), 1250 (C-O ether). H-NMR
(CDCl3) δ/ppm: 2.24–2.31 (m, 6H, CH2), 4.13 (t, 6H,
J = 6.0 Hz, OCH2), 4.22 (t, 6H, J = 6.0 Hz, OCH2),
1