Polyaromatic naphthalene

This chapter focuses on recent developments in the design and applications of fluorescent organic markers, such as coumarins, benzoxadiazoles, acridones, acridines, polyaromatics (naphthalene, anthracene, and pyrene), fluorescein, and rho-damine derivatives, which display maximum fluorescence emission in the UV/ visible region and have been applied in the labeling of relevant biomolecules, namely DNA, RNA, proteins, peptides, and amino acids, among others. 

Polyaromatics (naphthalene, acenaphthene, phenanthrene, anthracene, fluoranthene, pyrene)... 

Alkylphenols, ammonia, asbestos, chlorinated paraffins, 4-chloroaniline, cyanide, detergents, di- -butyl phthalate, polyaromatic hydrocarbons (PAHs e.g. anthracene, benzopyrene, methylcholanthrene, /i-naphthoflavone), nitrate, nitrite, petroleum oil, phenol, pentachlorophenol, 4-nitrophenol, dinitro-o-cresol, polychlorinated biphenyls (PCBs especially coplanar), polychlorinated dioxins, polybrominated naphthalenes, /i-sitosterol, sulfide, thiourea, urea, acid water, coal dust... 

An interesting reaction of dimsyl anion 88 is the methylation of polyaromatic compounds. Thus naphthalene, anthracene, phenanthrene, acridine, quinoline, isoquinoline and phenanthridine were regiospecifically methylated upon treatment with potassium t-butoxide and DMSO in digyme or with sodium hydride in DMSO123-125. Since ca. 50% of D was found to remain in the monomethyl derivative 93 derived from 9-deuteriophenanthrene 92, the mechanistic route shown in Scheme 2 was suggested125. 

Complexation with polyaromatic systems has also been observed. For instance, Mlnaphthalenelj, M = Cr (88,183), Mo (183), V (183), or Ti (183) may be synthesized in a solution reactor with the appropriate, metal vapors at liquid-nitrogen temperature. The Cr/naphthalene complex is less stable (dec. 160°C) than CrtCsH ) (m.p. 283-284° C). In fact, the naphthalene ligand is sufficiently labile to allow reaction under mild conditions, to afford CrL (L = CO or Bu NC), or Cr(naphth)Ls [L = PFj, P(OMe)3, or PMea]. The Mo, V, and Ti species are equally reactive. Analogous 1-methylnaphthalene complexes were also isolated (183). In addition, the complexes shown in Fig. 38 were synthesized by reaction, at the temperature of liquid nitrogen, of Cr atoms with 1,4-diphenylbutane (35, 201, 202). Analogous complexes were formed with 1,5-diphenylbutane (202). 

Oxidations of polyaromatics over Ti02 have been studied, for example, naphthalene oxidation to various oxygenated species [235] and phenanthrene to obtain coumarin derivatives as important compounds in the production of pharmaceuticals and dyes [236]. 

The remarkable feature in Table IV is that after the spectra have been adjusted for naphthalene, none of the bottoms products show the diaromatic or polyaromatic material which were present... 

Aromatic molecules with no polar substituent include benzene derivatives or other, more polyaromatic molecules, such as naphthalene, phenanthrene, and anthracene. These are polarizable. Paraffins are not polarizable by comparison. In gas-liquid systems, aromatic molecules will show stronger interactions with polar stationary phases that paraffins of comparable boiling point and, thus, polar stationary phases can aid in improving separation of substituted aromatics. 

Fig. 8. Separation of polyaromatic hydrocarbons using commercial stationary phases. (Reprinted with permission from [56]. Copyright 1997 VCH-Wiley). Conditions voltage 20 kV,capillary column 100 pm i. d., total length 33.5 cm, active length 25 cm, isocratic separation using 80 20 acetonitrile-50 mmol/1 TRIS buffer pH=8. Peaks thiourea (1), naphthalene (2), and flu-oranthrene (3)...

Polyaromatic hydrocarbons (PAH) are those which exists as combined aromatic ring structures represented by naphthalene (C10Hg) ... 

The Balz-Schiemann synthesis can be applied not only to substituted anilines but also to aminobiphcnyls1,131 or amino-substituted fused polyaromatic compounds, such as naphthalene,1114,119,129 anthracene,136 phenanthrene,1135 acenaphthene,133 fluorene,1,131,134 benzanthracene,130 136 pyrene,136 chrysene,136 fluoranthene,131 fluorenone,1,131 anthra-quinone,1,137,139,140 benzanthrone,1,117,118 phenanthraquinone,138 or xanthone.132 Fluorinated pyridines,1,141"146 methylpyridincs,126,147 149 pyridinecarboxylic acids,150 quinolines,1,151 isoquinolines,152 quinazolone,1 thiazoles,153,154 isothiazoles,156 benzothiazoles,157 thiadiazoles,155 and thiophenes154 can also be obtained from the corresponding aminated heterocycles. Modified Balz-Schiemann methods are recommended for amino nitrogen-containing heterocycles, the diazonium salts of which are rather water-soluble and unstable (a violent explosion was reported for pyridine-3-diazonium tetrafluoroborate).159 These new techniques have also been specially adapted for pyrazol-, imidazol-, or triazolamines which fail to react under classical conditions.158... 

Fig. 4.4 Analysis of polyaromatic hydrocarbons. Column two 100x4.6mm id in series, Ci8 bonded-phase packing 3 pm particles. Mobile phase acetonitrile-water, linear gradient from 65 to 90% in 20min, at 1.8mL min-1 inlet pressure 4500psig (31.0mPa) initial, 2700psig (18.6MPa) final ambient temperature UV detector at 254nm. Peaks 1, naphthalene 2, fluorene 3, acenaphthalene 4, phenanthrene 5,...

Polyaromatic hydrocarbons (benzene, toluene, naphthalene, acenaphthylene, fluor-ene, anthracene, 1,2-benzanthracene, phenol, acetone) ODS Hypersil, 5 pm Gradient acetonitrile-water (from 60 40 to 90 10) 500 mm x 75 pm i.d. 200 mm packed length, flow-injection analysis... 

Polyaromatic hydrocarbons and parabenes (ethyl-hexyl parabene, naphthalene, fluo-rene, phenanthrene, fluoranthene, pentylbenzene) Excil C18 Acetonitrile-Tris HC1 buffer pH 8.0 (80 20) 380 mm x 100 pm i.d. 85 mm packed length... 

Polyaromatic hydrocarbons Nucleosil ODS, 5 pm (naphthalene, fluorene, phenanthrene, anthracene), acetone... 

Polyaromatic hydrocarbons (naphthalene, fluorene, phen-anthrene, pyrene, benz[a]anthracene Linear polymer coated capillary [poly(N-tert.-butyl acrylamide-co-2-acrylamido-2-methyl-1 -propanesulfonic acid] Acetonitrile-50 mA/Tris buffer, pH 7.3 (30 70) 600 mm x 25 pm i.d. 450 mm effective column length 11... 

Dow Chemical also pioneered the shape-selective dialkylation of polyaromatics, e.g. naphthalene and biphenyl (see Fig. 2.12), using the same type of 3-DDM catalyst [39]. The products are raw materials for the production of the corresponding dicarboxylic acids, which are important industrial monomers for a variety of high performance plastics and fibres. 

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