Anthracene-based derivatives

A related anthracene-based ditopic sensor (11.28) has been constructed, which can recognise diammonium cations along the same lines as 3.103 (Section 3.12.3). Use of the anthracene-derived group as a spacer as in 11.27 gives fluorescent recognition of 11 N1 (Cl I NI I3+ guests as a function of spacer length.20... 

The raw materials used to synthesize organic dyes are commonly referred to as dye intermediates. Largely, they are derivatives of aromatic compounds obtained from coal tar mixtures. The majority of these derivatives are benzene, naphthalene, and anthracene based compounds. This section provides an overview of the chemical reactions used to prepare the key intermediates employed in dye synthesis. In this regard, emphasis is placed on halogenated, aminated, hydroxy-lated, sulfonated, and alkylated derivatives of benzene, naphthalene, and anthraquinone. 

A-Heterocycles were synthesized via insertion of 1,1-dimethylallene into Pd-G bonds of cyclopalladated a-tetralone ketimines. Insertion reactions of alkynes into the Pd-G bond of cyclopalladated ferrocenylimines have also been described.Biomimetic hydrolysis of benzoates has been carried out with a water-soluble cyclopalladated aryl oxime, which was proposed as a potential green catalyst. Ghiral cyclopalladated liquid crystals 88 were obtained from amino acids and could possibly serve as enantioselective catalysts. " Palladacycle 89 has been derived from an anthracene-based Schiff base. 

Many valuable chemicals can be recovered from the volatile fractions produced in coke ovens. Eor many years coal tar was the primary source for chemicals such as naphthalene [91-20-3] anthracene [120-12-7] and other aromatic and heterocycHc hydrocarbons. The routes to production of important coal-tar derivatives are shown in Eigure 1. Much of the production of these chemicals, especially tar bases such as the pyridines and picolines, is based on synthesis from petroleum feedstocks. Nevertheless, a number of important materials continue to be derived from coal tar. 

The synthetic procedure described is based on that reported earlier for the synthesis on a smaller scale of anthracene, benz[a]anthracene, chrysene, dibenz[a,c]anthracene, and phenanthrene in excellent yields from the corresponding quinones. Although reduction of quinones with HI and phosphorus was described in the older literature, relatively drastic conditions were employed and mixtures of polyhydrogenated derivatives were the principal products. The relatively milder experimental procedure employed herein appears generally applicable to the reduction of both ortho- and para-quinones directly to the fully aromatic polycyclic arenes. The method is apparently inapplicable to quinones having an olefinic bond, such as o-naphthoquinone, since an analogous reaction of the latter provides a product of undetermined structure (unpublished result). As shown previously, phenols and hydro-quinones, implicated as intermediates in the reduction of quinones by HI, can also be smoothly deoxygenated to fully aromatic polycyclic arenes under conditions similar to those described herein. 

Aminoanthracene forms a Schiff base with dimethylacetaldehyde (isobutyral-dehyde). This compound can be oxidized by peroxide under basic conditions to form 9-formamidoanthracene and acetone in dimethylformamide as a solvent [54, 55], CL from this system can be observed in other aprotic solvents as well. A limited amount of work has been done with the CLs of Schiff bases or anthracene derivatives. Presumably, this will change in the future. 

In realizing the poor film-forming property of 9,10-(diphenyl)anthracene, the Kodak group improved this property by designing a series of blue emitters based on further substituted anthracene derivatives. The chemical structures of these materials were patented in a U.S. Patent in 1999 [239], In their patent, Kodak also reported the EL data using one of these compounds as a host material and using TBP as a blue dopant (Scheme 3.62). The device structures is ITO/CuPc/NPD/anthracene compounds.5%TBP/Alq3/Mg Ag. The EL of the device showed blue emission with CIE color coordinates of (0.144, 0.196). Without the... 

Jiang et al. were the first to report a relatively stable blue OLED based on anthracene derivative JBEM (120) [240]. With the similar OLED structure as that used above by Kodak of ITO/CuPc/NPD/JBEM perylene/Alq/Mg Ag and using JBEM as a blue host material, the device shows a maximum luminance of 7526 cd/m2 and a luminance of 408 cd/m2 at a current density of 20mA/cm2. The maximum efficiency is 1.45 lm/W with CIE (0.14,0.21). A half-life of over 1000 h at initial luminance of 100 cd/m2 has been achieved. The authors also compared the device performance using DPVBI as a host, which gave them a less stable device. 

Recently, Kaska and coworkers ]37] reported a rigid PCP pincer system based on an anthracene backbone (29) (Scheme 13.17). The iridium derivative of this... 

The use of soluble metal catalysts makes it possible to react 8 and its substituted derivatives with aryl bromides and triflates at 100 °C. The catalyst systems that have been used are Pd2(dba>3 and ( )BINAP with calcium carbonate as base (dba = dibenz[ ,. ]anthracene, BINAP = 2,2-bis(diphenyl-phosphanyl)-l,l-binaphthyl)<2000JA2178>, and 2-(di-r-butylphosphino)biphenyltris(dibenzylideneacetone)palladium with sodium yt-butoxide as base <2003T3109>. 

Naphthalene- and anthracene-derived phenols did, however, almost uniformly precipitate (Table VI). In natural materials (not grapes or wines) which contain them they would be included in the formaldehyde precipitable group. Several primary amines capable of SchifFs base formation reacted with formaldehyde to lose their F-C oxidizability, but only the resorcinol analog, 3-aminophenol, precipitated (Table VIII). Sulfite also reacted but did not precipitate with formaldehyde, and the F-C oxidizability was suppressed (Table IX). The resorcinol derivative, 2,4-dimethoxycinnamic acid, formed a precipitate with formaldehyde, but it did not react appreciably in the F-C assay. 

A quantitative correlation has been derived based on experimental data for 11 aromatic compounds (biphenyl, naphthalene, anthracene, phenanthrene, pyrene, phenol, p-toluidine, p-nitrotoluene, and o-, m-, and p-nitrophenol) at 20°C [74] ... 

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