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DOI: 10.1055/s-0030-1260551
Perhydroazulenes - A New Class of Liquid Crystalline Materials
Publication History
Publication Date:
05 May 2011 (online)
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Abstract
A new class of mesogenic compounds, the perhydroazulenes, carrying substituents in their para positions (HAZ derivatives), has been synthesized. The new liquid crystalline materials display a broad enantiotropic nemantic mesophase slightly above room temperature without any additional smectic phase. Their physical properties reveal that the perhydroazulene moiety can replace the currently often used cyclohexyl and biscyclohexyl units in liquid crystalline materials.
Key words
liquid crystals - perhydrogenated azulenes - nematic materials - electrooptical displays
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References and Notes
Perhydroazulene-2,6-dione
Ethylene Ketal 9
¹H NMR (400.14
MHz, CDCl3): δ = 3.86
(s, 4 H), 2.30-2.48 (m, 4 H), 1.92-2.04 (m, 2
H), 1.77-1.88 (m, 2 H), 1.51-1.69 (m, 6 H) ppm. ¹³C
NMR (100.62 MHz, CDCl3): δ = 219.2, 111.5,
64.3 (+), 64.2 (+), 45.5 (+), 39.0 (-),
36.6 (+), 25.8 (+) ppm. MS (IE): m/z (%) = 210
(9) [M+], 126 (5), 99 (100),
86 (10), 55 (8); IR (diamond ATR): ν = 2990,
2931, 2880, 1731 cm-¹. UV (MeCN): λmax = 284
nm.
Liquid Crystalline
Derivative 16
¹H NMR (300.13 MHz,
CDCl3): δ = 6.86
(ddd, 1 H, J
1
= 0.3 Hz, J
2 = 2.4
Hz, J
3 = 8.9
Hz), 6.47 (dd, 1 H, J
1 = 2.0
Hz, J
2 = 7.6
Hz), 4.08 (q, 2 H, J = 7.0
Hz), 2.96-3.12 (m, 1 H), 2.19-2.38 (m, 2 H), 1.59-1.96
(m, 12 H), 1.43 (t, 3 H, J = 7.0 Hz),
1.23-1.38 (m, 4 H), 0.81-0.99 (m, 4 H) ppm. ¹³C
NMR (75.47 MHz, CDCl3): δ = 149.1
(dd, J
1 = 10.3
Hz, J
2 = 245.0 Hz),
145.9 (dd, J
1 = 3.0
Hz, J
2 = 8.2
Hz), 141.5 (dd, J
1 = 15.3
Hz, J
2 = 246.5
Hz), 129.1 (dd, J
1 = 1.5
Hz, J
2 = 12.3
Hz), 120.9 (+, dd, J
1 = 4.6
Hz, J
2 = 6.0
Hz), 109.3 (+, d, J = 2.5
Hz), 65.4 (+), 40.8 (+), 39.8 (-), 39.5
(-), 37.9 (+), 37.5 (-), 31.8 (+),
29.2 (+), 21.9 (+), 14.8 (-), 14.4 (-) ppm.
MS (IE): m/z (%) = 337
(22) [M + H+], 336
(100) [M+], 198 (13), 197
(20), 184 (52), 171 (14), 169 (12), 156 (36), 143 (24), 83 (15).
IR (diamond ATR): ν = 2931,
2889, 2857, 1511, 1473, 1296, 1116, 1081, 805 cm-¹.
UV (CH2Cl2): λmax = 229,
268 nm. For mp see Table
[¹]
.