57604-03-2

Upstream product

• 623-27-8 terephthalaldehyde, 
• 589-87-7 1,4-bromoiodobenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 106-38-7 para-bromotoluene 
• 624-38-4 para-diiodobenzene 
• 696-61-7 4-tolylmagnesium chloride 
• 113652-52-1 1,4-bis-(α,β-dibromo-4-methyl-phenethyl)-benzene 

Relevant academic research and scientific papers

Achieving non-doped deep-blue OLEDs by applying bipolar imidazole derivatives

In this work, we designed and synthesized two novel bipolar deep-blue emitting materials, 2-(4'-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-yl)-1 (4(tri-fluoromethyl) phenyl)-1H-phenanthro[9,10-d] imidazole (CzB-FMPPI) and 9-(4'-(4,5-diphenyl-1 (4-(trifluoromethyl) phenyl)-1H-imidazole-2-yl)-[1,1′-biphenyl]-4-yl)-9H-carbazole (CzB-FMPIM). Among them, carbazole and phenanthroimidazole are bridged linkage by the biphenyl ring and act as electron-donating part. The CF3-substituted phenyl ring applies as strong electron-withdrawing moiety. The exhibit highly twisted molecular configuration of two compounds efficiently shorten π-conjugation and inhibit intermolecular interaction, resulting in superior thermal stability and deep blue emission. High decomposition temperature of 431 °C and 414 °C, glass transition temperature of 150 °C and 135 °C for CzB-FMPPI and CzB-FMPIM, respectively, had been achieved. As a consequence of breaking the conjugation of phenanthroimidazole chromophore, CzB-FMPIM achieves an 8 nm blue-shifted emission compared with CzB-FMPPI. CzB-FMPPI exhibits a higher relative fluorescence quantum yield of 92.5% than 83.3% of CzB-FMPIM. Moreover, bipolar property was observed in both compound and homogeneous amorphous films were deposited and applied in the non-doped deep-blue OLEDs. The devices based on two emitters showed maximum luminance of 6667 cd/m2 and 3084 cd/m2, maximum EQE of 4.10% and 3.17%, respectively. Commission International de l'éclairage (CIE) coordinates of CzB-FMPIM based device achieved (0.15, 0.07) which is extremely close to the NTSC standard blue CIE (0.14, 0.08).

Alkynyl?B(dan)s in Various Palladium-Catalyzed Carbon?Carbon Bond-Forming Reactions Leading to Internal Alkynes, 1,4-Enynes, Ynones, and Multiply Substituted Alkenes

It was found that the C(sp)?B(dan) bond of alkynyl?B(dan)s can be directly used for palladium-catalyzed carbon?carbon bond-forming reactions with aryl(alkenyl) halides and allylic carbonates as electrophiles, thus delivering unsymmetrical internal alkynes and unconjugated 1,4-enynes, respectively. With acyl chlorides as electrophiles, ynone synthesis is also promoted by a palladium catalyst with the assistance of a copper co-catalyst. These reactions can be achieved as more convenient one-pot reactions, without isolating the alkynyl?B(dan) formed in situ by the zinc-catalyzed dehydrogenative borylation of alkynes with HB(dan). In addition to direct C(sp)?B(dan) bond transformations, the C≡C bond in an alkynyl?B(dan) proved to be a promising scaffold for the construction of a multisubstituted alkene, which is synthesized by diboration of the C≡C?B(dan) moiety, leading to a triborylalkene followed by iterative regio- and stereoselective Suzuki?Miyaura cross-coupling reactions. As one example, the synthesis of the ethene with four different aryl groups, p-MeC6H4, p-MeOC6H4, p-NCC6H4, and p-F3CC6H4, was attained in high overall yield of 64% in six steps starting from the terminal alkyne, p-MeC6H4C≡CH. Besides these synthetic applications of the alkynyl?B(dan), the scope of the alkynyl substrate in the zinc-catalyzed dehydrogenative borylation was expanded to enhance the reliability as a provider of the alkynyl?B(dan). Consequently, 42 alkynes were found to participate in the dehydrogenative borylation as substrates; these are alkyl-, alkenyl-, aryl-, heteroaryl-, ferrocenyl-, silyl-, and borylalkynes, with or without a variety of functional groups. Lastly, a new method for preparing HB(dan), as a sulfide-free, cost-saving, and reaction-time-saving route, is disclosed. (Figure presented.).

Three-Component One-Pot Synthesis of Unsymmetrical Diarylalkynes by Thermocontrolled Sequential Sonogashira Reactions Using Potassium Ethynyltrifluoroborate

Unsymmetrical diarylalkynes were synthesized in moderate to good yields through a three-component one-pot procedure involving thermocontrolled sequential Sonogashira reactions with potassium ethynyltrifluoroborate and two different reactive aryl halides. The one-pot procedure was initiated by the palladium/copper-catalyzed Sonogashira coupling of potassium ethynyltrifluoroborate to an aryl iodide or electron-deficient aryl bromide at 40 °C. Following a subsequent deboronative Sonogashira reaction of the in situ generated potassium (arylethynyl)trifluoroborate, a second coupling to a less-active electron-rich aryl bromide at 80 °C, without any additional palladium/copper catalyst or base, gave rise to unsymmetrical diarylalkynes.

1-(4-alkylphenylethynyl)-4-(alkylphenylethynyl)-benzene

A tolan derivative useful as a component of liquid crystal materials and being superior to conventional tolan derivatives in the characteristics of Δn and viscosity, and a liquid crystal composition containing the same are provided, which tolan derivative is expressed by the formula STR1 wherein R1 and R2 each represent an alkyl group of 1 to 10 carbon atoms.