Synlett 2015; 26(13): 1905-1910
DOI: 10.1055/s-0034-1379930
letter
© Georg Thieme Verlag Stuttgart · New York

Towards New Oligomesogenic Phosphonic Acids as Stabilizers of Nanoparticles Colloids in Nematic Liquid Crystals

Maksym F. Prodanov*
State Scientific Institution ‘Institute for Single Crystals’, NAS of Ukraine, 60 Lenin Ave., Kharkiv, Ukraine   eMail: prodanov@isc.kharkov.com
,
Maksym Y. Diakov
State Scientific Institution ‘Institute for Single Crystals’, NAS of Ukraine, 60 Lenin Ave., Kharkiv, Ukraine   eMail: prodanov@isc.kharkov.com
,
Ganna S. Vlasenko
State Scientific Institution ‘Institute for Single Crystals’, NAS of Ukraine, 60 Lenin Ave., Kharkiv, Ukraine   eMail: prodanov@isc.kharkov.com
,
Valerii V. Vashchenko
State Scientific Institution ‘Institute for Single Crystals’, NAS of Ukraine, 60 Lenin Ave., Kharkiv, Ukraine   eMail: prodanov@isc.kharkov.com
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Publikationsverlauf

Received: 10. April 2015

Accepted after revision: 04. Mai 2015

Publikationsdatum:
07. Juli 2015 (online)


Abstract

Several synthetic strategies for the construction of linear and branched oligomesogenic phosphonic acids are examined, which differ in the method of building the key bimesogen unit. An efficient synthetic approach to the most promising compounds employs regioselective Kumada cross-coupling between [11-(4′-pentylbiphenyl-4-yl)undecyl]magnesium bromide and 4-(11-bromoundecyl)-4′-iodobiphenyl as the key step. Preliminary studies on the ability of the new ligands to stabilize nanoparticles colloids in nematic liquid crystals are undertaken for the example of quantum dots.

Supporting Information

 
  • References and Notes

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  • 36 To magnesium turnings (0.08 g, 3.3 mmol), activated with iodine, anhydrous THF (100 mL) was added under Ar. To this mixture, a few drops of 4-(11-bromoundecyl)-4′-pentylbiphenyl solution in THF was added. The mixture was heated to 80 °C and a solution of 4-(11-bromoundecyl)-4′-pentylbiphenyl (15; 1.35 g, 2.9 mmol) was added dropwise during 1.5 h. The obtained Grignard reagent was pumped through a Teflon capillary tube into a dropping funnel under argon pressure. The Grignard reagent was then added dropwise at r.t. to a stirred degassed suspension of PdCl2(dppf) catalyst (4 mol%) and 4-(11-haloundecil)-4′-iodobiphenyl (19a,b; 1.14 g, 2.2 mmol) for several minutes under Ar. The mixture was stirred for 1 h and then poured into 17% solution of ammonium chloride in water. The resulting mixture was extracted with toluene; the organic extracts were collected, washed with water, dried over Na2SO4, filtered, and evaporated to dryness. The crude product was recrystallized from a mixture of MeCN–CH2Cl2 (50%, 30 mL). Yield: 1.34 g (79%). According to HPLC analysis in combination with NMR spectroscopy (see the Supporting Information) the obtained mixture contained 33% 20b. Mp 72–74 °C. IR (KBr): 3033, 2918, 2847, 1909, 1499, 1468, 1401, 1135, 1003, 809, 793, 763, 718, 648, 591, 516, 483 cm–1. 1H NMR (CDCl3, 200 MHz): δ = 0.91 (br t, 3 H, CH3), 1.18–1.50 [m, 32 H, (CH2)16], 1.65 [m, 8 H, (CH2)4], 1.86 (m, 2 H, CH2), 2.64 [t, J = 7.7 Hz, 8 H, (CH2)4], 3.40 (t, J = 7.4 Hz, 1.41 H, CH2), 3.53 (t, J = 6.6 Hz, 0.59 H, CH2), 7.24 (d, J = 8.4 Hz, 8 H, ArH), 7.50 (d, J = 8.4 Hz, 8 H, ArH). MS (MALDI TOF): m/z = 718.5 [M]+ (C51H71Cl), 757.5 [M + K]+ (C51H71ClK), 764.5 [M + 2H]+ (C51H73Br), 808.5 [M+2Na]+ (C51H71BrNa2), 840.5 [M + 2K]+ (C51H71 BrK2).
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