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Synlett 2011(9): 1273-1276  
DOI: 10.1055/s-0030-1260551
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Perhydroazulenes - A New Class of Liquid Crystalline Materials

Henning Hopf*a, Zakir Hussaina, Rajeev S. Menona, Vitaly Raeva, Peter G. Jones*b, Ludwig M. Pohla
a Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
Fax: +49(531)3915388; e-Mail: H.Hopf@tu-bs.de;
b Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
Fax: +49(531)3915387; e-Mail: P.Jones@tu-bs.de;
Further Information

Publication History

Received 31 January 2011
Publication Date:
05 May 2011 (online)

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Corrected by:

Perhydroazulenes - A New Class of Liquid Crystalline MaterialsSynlett 2011; 2011(12): 1788-1788
DOI: 10.1055/s-0029-1260943

Corrected by:

Perhydroazulenes - A New Class of Liquid Crystalline MaterialsSynlett 2011; 22(14): 2104-2104
DOI: 10.1055/s-0029-1261190

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

    References and Notes

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5

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.

7

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] .