Perylene syntheses

Chabert, J. F. D. Joucla, L. David, E. Lemaire, M. An efficient phosphine-free Pd coupling for the synthesis of new 2-arylbenzo[b]thio-phenes. Tetrahedron 2004, 60, 3221-3230. Chow, S.-Y. Palmer, G. J. Bowles, D. M. Anthony, J. E. Perylene synthesis by the parallel cycloaromatization of adjacent enediynes. Org. Lett. 2000, 2, 961-963. 

Takahashi, M., Suzuki, Y., Ichihashi, Y., Yamashita, M., Kawai, H. l,3,8,10-Tetrahydro-2,9-diazadibenzo[crf, /m]perylenes synthesis of reduced perylene bisimide analogues. Tetrahedron Lett. 48, 357-359 (2007)... 

Perylene-3,4,9,10-bis(dicarbonamide) electrical conductivity, 1, 358 Perylene hexafluoroarsenate conductors, 1, 355 Perylene vat dyes, 1, 336-337 Pestalotin synthesis, 3, 841 Pethidine... 

Perylenes (70) are diimides of perylene-3,4,9,10-tetracarboxylic acid, and may be prepared by reaction of the bis-anhydride of this acid, 89 (1 mol) with the appropriate amine (2 mol) in a high-boiling solvent as illustrated in Scheme 4.11. The synthesis of perinones 71 and 72 involves condensation of naphthalene-1,4,5,8-tetracarboxylic acid with benzene-1,2-diamine in refluxing acetic acid. This affords a mixture of the two isomers, which may be separated by a variety of methods, generally involving their differential solubility in acids and alkalis. 

Synthesis of Radical Cation Perchlorates and Subsequent Coupling with NucleophilesT Syntheses of the radical cation perchlorates of BP and 6-methylBP (12) were accomplished by the method reported earlier for the preparation of the perylene radical cation (13,14). More recently we have also synthesized the radical cation perchlorate of 6-fluoroBP (15). Oxidation of the PAH with iodine in benzene in the presence of AgClO. instantaneously produces a black precipitate containing the radical cation perchlorate adsorbed on Agl with... 

Mikroyannidis JA, Stylianakis MM, Sharma GD, Balraju P, Roy MS (2009) A novel alternating phenylenevinylene copolymer with perylene bisimide units synthesis, photophysical, electrochemical, and photovoltaic properties. J Phys Chem C113 7904-7912... 

SCHEME 2.51 Synthesis of perylene-fluorene and a-cyanostilbene-fluorene copolymers via Yamamoto coupling. (From Klarner, G., Lee, J.-I., Davey, M.H., and Miller, R.D., Adv. Mater., 11, 115, 1999.)... 

The primary starting material for the synthesis of perylene tetracarboxylic acid pigments is the dianhydride 71. It is prepared by fusing 1,8-naphthalene dicar-boxylic acid imide (naphthalic acid imide 69) with caustic alkali, for instance in sodium hydroxide/potassium hydroxide/sodium acetate at 190 to 220°C, followed by air oxidation of the molten reaction mixture or of the aqueous hydrolysate. The reaction initially affords the bisimide (peryldiimide) 70, which is subsequently hydrolyzed with concentrated sulfuric acid at 220°C to form the dianhydride ... 

A different route proceeds by alkali fusion of the corrspondingly substituted naphthalic acid imide. This pathway parallels the synthesis of perylene tetracarboxylic acid diimide 70 (Sec. 3.4.1.1). The method is particularly suited to aliphatic amines. 

Some fimctionalized materials have also been prepared by coprecipitation at low supersaturation. A perylene chromophore, for example, has been intercalated into LDH in an attempt to prepare stabihzed pigments [40]. Catalyt-ically active species have also been introduced into the interlayers of LDHs by direct synthesis, e.g. the intercalation of (PWi204o) or (SiWi204o) gives catalysts or catalyst precursors containing interlayer polyoxometalate anions [41]. Vein et al. reported the synthesis of Zr-containing LDH-Hke... 

An alternative theory associates electron transfer with transfer of a state of aromaticity from molecule to molecule within the stack (77AG(E)519). Efficient charge transport was identified with conversion of a neutral, antiaromatic system to a charged, aromatic radical by electron transfer. This interpretation has been eroded by the synthesis of conductors from aromatic systems such as perylene hexafluoroarsenate (81MI11301) or polypyrrole tetrafluoroborate (80CC397, 81MI11300) where an electron is transferred from a neutral, aromatic molecule to a non-aromatic charged radical. 

Similarly, Torres et al. also reported the preparation of perylene-Pc assemblies 5 (Fig. 5). The synthesis of these triads was thereby accomplished via palladium-catalyzed cross-coupling pursuing two different routes [46], First preparing the perylenediimide with two bromine units in positions 1 and 7 and subsequent... 

Scheme 3 Synthesis of the chiral silicone perylene bichromophores 12...

Synthesis of Poly-peri-naphthalene. Kaplan et al. have prepared carbon films with relatively high electrical conductivity (250 S/cm) by pyrolyzing a polyfunctional monomer, 3> 9> 10-perylene-... 

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