Distyryl-benzene

Pond SJK, Tsutsumi O, Rumi M et al (2004) Metal-ion sensing lluorophores with large two-photon absorption cross sections aza-crown ether substituted donor-acceptor-donor distyryl benzenes. J Am Chem Soc 126 9291-9306... 

Bis(styrylb benzene or Distyryl-benzene, C22H)8. One isomer l,4-Bis(styryl)-benzene is described in Beil 5,(361)... 

A new branched carbazole derivative with phenyl ethylene moieties attached, l,3,5-tris(2-(9-ethylcarbazyl-3)ethylene)benzene (TECEB, 41) (Scheme 3.15), was prepared as a HTM for OLEDs [86], TECEB has a HOMO energy level of —5.2 eV and hole-drift mobility of 1(T 4 cm2/(V s), comparable to NPD. The device performance (maximum luminance of about 10,000 cd/m2 and current efficiency of 3.27 cd/A) in a standard HTL/tris-(8-hydroxyquino-line) aluminum double-layer device is also comparable to NPD, but TECEB has a higher Tg (130°C) and its ease of synthesis is superior to NPD. Distyryl units linked to a TPD derivative, A, A"-bis(4-(2,2-diphenylethenyl)-phenyl)-jY,jV -di(p-tolyl)-bendidine (DPS, 42) (Scheme 3.15), reported by Yamashita and coworkers, showed good hole transport properties and improved thermal stability compared with the parent TPD [87]. 

Reaction of phenylacetylene with Te/KOH/SnCf A mixtnre of 6.4 g of tellurium, 42 g of potassium hydroxide, 22.6 g of SnCl2 2H20, 10.2 g of phenylacetylene, 20 mL of toluene, 60 mL of water and 1.2 g of Adogen 464 was heated (80-97°C) with vigorous stirring for 7 h. The organic layer was separated, and the aqneons layer was extracted with benzene. The benzene was removed under vacnnm. The residne was dissolved in a small amount of ether, poured into 200 mL of isopropyl alcohol, and placed in the refrigerator for 3 days. The yellow crystals of distyryl telluride (2.5 g, yield 15%) and the red needle crystals of distyryl ditelluride (0.7 g, yield 6%) were separated. 

Reaction of phenylacetylene with Te/K0H/N2HfXH20f (Z,Z)-distyryl telluride. A mixture of Te (12.8 g), phenylacetylene (20.4 g), KOH (84 g), NjH XHjO (120 mL), H2O (24 mL), toluene (40 mL), and AlKjN MeCl (1 g) was heated (100-110°C) with a stirring of 6 h. The mixtnre was dilnted with water and extracted with benzene. The organic layer was washed with water, dried over K2CO3 and evaporated. The residue was dissolved in ether, the ether solntion was ponred into ethanol and put into refrigerator. After several days yellow cristals of the tellnride (16.7 g, 50% yield) were separated and dried. 

Z,Z)-Distyryl Tellurium2 A mixture of 12.8 g (0.1 mol) tellurium, 20.4 g (0.2 mol) phenylacetylene, 84 g (1.5 mol) potassium hydroxide, 120 ml (2.5 mol) hydrazine hydrate, 24 ml water, 40 ml toluene, and 1 g trialkylmethylammonium chloride is stirred and heated at 100 to 110° for 6 h. The mixture is diluted with water and extracted with benzene. The organic layer is washed with water, dried with potassium carbonate, filtered and the solvent evaporated from the filtrate. The residue is dissolved in diethyl ether, and the solution is poured into ethanol. After several days in the refrigerator yellow crystals of distyryl tellurium formed yield 50%. 

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