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K. Niknam et al.
PAPER
(E)-1-[2-(4-Methansulfonylphenyl)vinyl]-4-bromobenzene
(MSPVBB)
1,4-Bis(4-bromostyryl)-2,5-dimethylbenzene (1e)
Yellow solid; mp 238–240 °C.
White solid; mp 151–154 °C.36
IR (KBr): 3005 (C–H), 2910 (C–H), 1520 (C=C), 1480 (C=C), 960
(C–H), 805 (C–H) cm–1.
1H NMR (500 MHz, DMSO-d6): d = 2.41 (s, 6 H, CH3), 7.15 (d,
J = 16.2 Hz, 2 H), 7.41 (d, J = 16.2 Hz, 2 H), 7.54–7.63 (m, 10 H).
MS (EI, 70 eV): m/z (%) = 450 (1.90), 468 (3.70), 466 (1.95) [M]+,
414 (37.03), 412 (35.18), 269 (38.88), 248 (100), 189 (50.92), 149
(49.74), 95 (12.96), 76 (10.16), 57 (15.74).
IR (KBr): 3010 (C–H), 2920 (C–H), 1590 (C=C), 1290 (SO2), 1140
(SO2) cm–1.
1H NMR (500 MHz, CDCl3): d = 3.10 (s, 3 H, CH3), 7.14 (d,
J = 16.3 Hz, 1 H), 7.21 (d, J = 16.3 Hz, 1 H), 7.43 (d, J = 8.5 Hz,
2 H), 7.55 (d, J = 8.5 Hz, 2 H), 7.69 (d, J = 8.4 Hz, 2 H), 7.95 (d,
J = 8.4 Hz, 2 H).
13C NMR (125 MHz, CDCl3): d = 45.0, 123.0, 127.5, 127.7, 128.3,
128.8, 131.8, 132.4, 135.7, 139.5, 142.9.
Anal. Calcd for C24H20Br2: C, 61.56; H, 4.31; Br, 34.13. Found: C,
61.38; H, 4.46.
2-(N-{4-[4-(4-Methylsulfonyl)styryl]styryl}phenyl)-N-ethyl-
aminoethanol (1b)
Orange solid; mp 274–276 °C.
1,4-Bis(4-chlorostyryl)-2,5-dimethylbenzene (1f)
Yellow solid; mp 187–190 °C.
IR (KBr): 3010 (C–H), 1480 (C=C), 800 (C–H).
IR (KBr): 3500 (O–H), 3020 (C–H), 1585 (C=C), 1519 (C=C),
1292 (SO2), 1145 (SO2) cm–1.
1H NMR (250 MHz, DMDO-d6): d = 2.41 (s, 6 H, CH3), 7.18 (d,
J = 16.3 Hz, 1 H), 7.33 (d, J = 16.3 Hz, 1 H), 7.43 (d, J = 8.4 Hz,
2 H), 7.62–7.66 (m, 4 H), 7.67–7.76 (m, 6 H).
MS (EI, 70 eV): m/z (%) = 380 (92.70) [M++2], 379 (36.45)
[M++1], 378 (100) [M]+, 328 (26.04), 189 (17.70), 139 (12.50), 115
(6.24), 97 (3.12), 77 (6.24), 57 (4.16).
1H NMR (500 MHz, DMSO-d6): d = 1.09 (t, J = 6.9 Hz, 3 H, CH3),
3.22 (s, 3 H, CH3), 3.36–3.43 (m, 4 H, CH2N), 3.53–3.56 (m, 2 H,
CH2O), 4.72 (t, J = 5.4 Hz, 1 H, OH), 6.67 (d, J = 8.8 Hz, 2 H), 6.95
(d, J = 16.3 Hz, 1 H), 7.17 (d, J = 16.3 Hz, 1 H), 7.35 (d,
J = 16.4 Hz, 1 H), 7.40 (d, J = 8.7 Hz, 2 H), 7.46 (d, J = 16.4 Hz,
1 H), 7.55 (d, J = 8.3 Hz, 2 H), 7.62 (d, J = 8.3 Hz, 2 H), 7.84 (d,
J = 8.4 Hz, 2 H), 7.90 (d, J = 8.3 Hz, 2 H).
Anal. Calcd for C24H20Cl2: C, 75.99; H, 5.32; Cl, 18.69. Found: C,
75.81; H, 5.50.
MS (EI, 70 eV): m/z (%) = 447 (7.08) [M]+, 416 (17.32), 342
(81.88), 285 (7.87), 236 (12.59), 178 (20.47), 149 (18.89), 111
(22.04), 97 (43.30), 83 (56.69), 57 (94.48), 43 (100).
1,4-Bis(4-chlorostyryl)benzene (1g)
Yellow-green solid; mp 296–299 °C (Lit.10 294–295 °C).
IR (KBr): 3000 (C–H), 1580 (C=C), 1480 (C=C), 820 (C–H) cm–1.
1H NMR (250 MHz, DMSO-d6): d = 7.30 (m, 4 H), 7.41–7.46 (m,
8 H), 7.63–7.65 (m, 4 H).
MS (EI, 70 eV): m/z (%) = 352 (82.35) [M+ + 2], 351 (31.76) [M+ +
1], 350 (100) [M]+, 202 (34.11), 178 (67.05), 149 (91.76), 113
(17.32), 89 (22.33), 71 (25.98), 57 (37.64).
Anal. Calcd for C27H29NO3S: C, 72.45; H, 6.53; N, 3.12; S, 7.16.
Found: C, 72.28; H, 6.66; N, 2.98, S, 6.97.
1,4-Bis{2-[N-ethyl-N-(4-vinylphenyl)amino]ethanol}benzene
(1c)
Yellow solid; mp 215–217 °C.
IR (KBr): 2922, 1160, 1520, 1360, 1267, 1180, 1051, 964, 823 (C–
H) cm–1.
1,4-Bis(4-fluorostyryl)-2,5-dimethylbenzene (1h)
1H NMR (500 MHz, DMSO-d6): d = 1.09 (t, J = 7.0 Hz, 6 H, CH3),
3.35–3.42 (m, 8 H, CH2N), 3.52–3.56 (m, 4 H, CH2O), 4.71 (t,
J = 5.4 Hz, 2 H, OH), 6.67 (d, J = 8.8 Hz, 4 H), 6.9 (d, J = 16.3 Hz,
2 H), 7.08 (d, J = 16.3 Hz, 2 H), 7.38 (d, J = 8.7 Hz, 4 H), 7.47 (s,
4 H).
MS (EI, 70 eV): m/z (%) = 456 (94.49) [M]+, 426 (38.58), 425
(100), 412 (35.43), 381 (47.24), 365 (36.22), 352 (24.41), 313
(27.56), 264 (25.19), 236 (24.41), 197 (51.97), 183 (24.41), 169
(25.98), 109 (16.53), 97 (25.19), 83 (25.98), 69 (25.98), 57 (32.28),
43 (24.41).
Pale-yellow solid; mp 196–198 °C.
IR (KBr): 3015 (C–H), 1485, 1375, 1060, 1000, 960, 845, 800 (C–
H) cm–1.
1H NMR (500 MHz, CDCl3): d = 2.46 (s, 6 H, CH3), 7.02 (d,
J = 16.1 Hz, 2 H), 7.09 (t, J = 8.6 Hz, 4 H), 7.25 (d, J = 16.1 Hz,
2 H), 7.44 (s, 2 H), 7.51–7.54 (m, 4 H).
13C NMR (125 MHz, CDCl3): d = 20.0, 116.0, 116.1, 126.3, 127.6,
128.4, 128.5, 128.7, 133.9, 135.1 (d, JC–F = 186.8 Hz).
Anal. Calcd for C24H20F2: C, 83.21; H, 5.82; F, 10.97. Found: C,
83.05; H, 6.01.
Anal. Calcd for C30H36N2O2: C, 78.91; H, 7.95; N, 6.13. Found: C,
78.74; H, 8.06; N, 5.97.
Acknowledgment
1,4-Bis[4-(methylsulfonyl)styryl]benzene (1d)
Yellow-greenish solid; mp >300 (dec.).
We are thankful to the Persian Gulf University Research Council
for partial support of this work and Dr Clare Vickers for her helpful
comments. We are also thankful to Dr Mohammad Reza
Shamsaddini for his helpful corrections.
IR (KBr): 3020 (C–H), 2921 (C–H), 1591 (C=C), 1506 (C=C), 1305
(SO2), 1144 (SO2) cm–1.
1H NMR (500 MHz, DMSO-d6): d = 3.23 (s, 6 H, CH3), 7.43 (d,
J = 16.4 Hz, 2 H), 7.51 (d, J = 16.4 Hz, 2 H), 7.71 (s, 4 H), 7.87 (d,
J = 8.2 Hz, 4 H), 7.92 (d, J = 7.9 Hz, 4 H).
References
MS (EI, 70 eV): m/z (%) = 440 (23.53), 439 (44.70), 438 (100)
[M]+, 368 (22.35), 339 (17.64), 313 (36.47), 299 (30.59), 264
(43.53), 236 (40.00), 97 (53.00), 83 (60.00), 69 (69.90), 57 (95.29),
43 (91.77).
(1) Tang, C. W.; Van Slyke, S. A.; Chen, C. H. J. Appl. Phys.
1989, 65, 3610.
(2) Renak, M. L.; Bartholomew, G. P.; Wang, S.; Ricatto, P. J.;
Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1999, 121,
7787.
(3) Luo, F. T.; Tao, Y. T.; Ko, S. L.; Chuen, C. H.; Chen, H.
J. Mater. Chem. 2002, 12, 47.
Anal. Calcd for C24H22O4S2: C, 65.73; H, 5.06; S, 14.62. Found: C,
65.54; H, 5.25; S, 14.45.
Synthesis 2011, No. 10, 1609–1615 © Thieme Stuttgart · New York