Synthesis and mesomorphic properties of calamitic malonates and cyanoacetates tethered to 4-cyanobiphenyls

Abstract

Summary4-Cyano-1,1'-biphenyl derivatives bearing ω-hydroxyalkyl substituents were reacted with methyl 3-chloro-3-oxopropionate or cyanoacetic acid, giving liquid-crystalline linear malonates and cyanoacetates. These compounds formed monotropic nematic phases at 62 °C down to ambient temperature upon cooling from the isotropic liquid. The mesomorphic properties were investigated by differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction (WAXS).

Charged Triazole Cross-Linkers for Hyaluronan-Based Hybrid Hydrogels

“…Following the method by Kress [ 28 ], 1,ω-diols 3 were treated with HBr in toluene under Dean Stark conditions to provide the bromoalcohols 4 in good yields, except for 4-bromobutanol 4a due to the formation of THF as a by-product. Subsequent nucleophilic substitution with potassium phthalimide gave the hydroxy phthalimides 5 with a 49%–90% yield [ 29 ].…”

Microwave and Ultrasound Assisted First Synthesis of 12-Hydroxyhentriacontane

“…OH CAUTION: Pyridinium dichromate is toxic and its preparation can be hazardous. (3): 20 A mixture of 1, 10-decanediol (0.3 g, 1.72 mmol), 48% aq. hydrogen bromide (0.29 g, 3.58 mmol) and tetrabutylammonium iodide (0.12 g, 0.34 mmol) was subjected to MWI at 355 W for 5 min.…”

“…: 20 A mixture of 1, 10-decanediol (0. 21 10-Bromodecan-1ol (0.24 g, 1.0 mmol) in dry THF (1mL) was mixed with 3,4-dihydro-2H-pyran (0.11 g, 1.25 mmol) and iodine (0,05 g, 0.2 mmol).…”

Mesomorphic properties of cyanobiphenyl dimers with a central malonate unit

“…7,28.2,28.8,29.4,29.5,29.6,29.6,29.6,32.8,32.8 (12 × CH 2 ), 34.0 (BrCH 2 ), 63.1 (OCH 2 ) ppm. [2] 2.2 General Procedure GP 2: Synthesis of ω-Hydroxyalkyloxy-Cyanobiphenyles (6) Based on a procedure by Kress [10] , 4'-Hydroxy-[1,1'-biphenyl]-4-carbonitrile 5 (10.2 mmol) and potassium carbonate (30.7 mmol) were suspended in acetonitrile (50 mL), the respective ω-Bromoalkanole 4 (14.3 mmol) was added and the reaction mixture was heated under reflux.…”

“…10576( 1) -882(3) -2885( 1) 57( 1) N( 2) 4401( 1) -962( 3) 12657( 1) 60( 1) O( 3) 8589( 1) 4574( 2) 529( 1) 41( 1) C( 3) 7424( 2) 4512( 3) 3363( 2) 49( 1) C( 4) 7542( 2) 3635( 3) 2826( 1) 49(1) C( 5) 7647( 1) 4597( 3) 2289( 1) 44( 1) O( 6) 6568( 1) 4704( 2) 9436( 1) 44(1) C( 6) 7873( 1) 3723( 3) 1818( 1) 41(1) C (7) 8110( 1) 4654( 3) 1369( 1) 41( 1) C( 8) 8397( 1) 3691( 3) 978( 1) 42(1) C( 9) 8860( 1) 3832( 3) 138( 1) 37( 1) C (10) 9015( 1) 4673(3) -324( 1) 39(1) C (11) 9283( 1) 4005(3) -737( 1) 38( 1) C(…”