9,10-Diphenyl anthracene

Bei der Reduktion aromatischcr Kohlenwasserstoffe in Gegenwart von Alkylhalogeniden kann Elektroche-milumineszcnz auftreten ebcnso bei der Elektrolyse von 9,10-Dichlor-9,10-dihydro-9,10-diphenyl-anthracen in aprotischen Solventien . 

In complex organic molecules calculations of the geometry of excited states and hence predictions of chemiluminescent reactions are very difficult however, as is well known, in polycyclic aromatic hydrocarbons there are relatively small differences in the configurations of the ground state and the excited state. Moreover, the chemiluminescence produced by the reaction of aromatic hydrocarbon radical anions and radical cations is due to simple one-electron transfer reactions, especially in cases where both radical ions are derived from the same aromatic hydrocarbon, as in the reaction between 9.10-diphenyl anthracene radical cation and anion. More complex are radical ion chemiluminescence reactions involving radical ions of different parent compounds, such as the couple naphthalene radical anion/Wurster s blue (see Section VIII. B.). 

Stevens, N. (1953) Vapour pressures and the heats of sublimation of anthracene and of 9 10-diphenyl anthracene. J. Chem. Soc. (Lond.) 2973-2974. 

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... 

Figure 8.8. Examples of nonexponential fluorescence decay curves 9,10-diphenyl-anthracene on alumina for chromatographic purposes (Uhl.Oelkrug, unpublished results) (unnumbered curves time profiles of the excitation pulse, 2 - 360 nm). Upper left effect of environment (1) high vacuum, (2) liquid n-hexane. c=3/tmol g"1,2 =440 nm. Upper right effect of fluorescence wavelength (1) 2 = 500 nm, (2) 440 nm, (3) 406 nm c=3 /tmol g 1. Lower left effect of surface loading (1) 3 /rmol g (2) 0.13 mol g , (3) 0.02/r mol g"1 2e=440. Lower right effect of sample thickness (l) d - . (2) d - 0 c - 3 /tmol g 1, 2 = 440 nm.

These alternatives may be distinguished by examining the concentration dependence of the molecular fluorescence yield given by Eq. (1) the observation of self-quenching invalidates condition (b) and provides strong evidence for photoassociation in systems where qD 0. These criteria are applied to the behavior of anthracene and certain of its derivatives in Table V, from which it is concluded that photoassociation of 9,10-diphenyl-anthracene (as in 9,10-dimethyl-1,2-benzanthracene and rubrene) is prohibited by steric hindrance of the bulky substituents (Table III). 

The addition of O2 (whether or A ) to 138 or 4 has apparently not been studied theoretically although selection rules for singlet oxygen reactions/ interpretation of substituent effects and orbital correlations for homolytic fission and re-formation of the peroxide bond in 9,10-diphenyl-anthracene peroxide and rubrene peroxide have been published. 

Although thiophene derivatives, e.g., tetraphenylthiophene XXI and XXII70 do not appear to form photoperoxides sulfurated 9,10-diphenyl-anthracenes XXIII and cerothiene XXIV derivatives have been reported to form transannular peroxides of the type A on irradiation in the presence of oxygen.209,210... 

Jonah et al. [178] found that the fluorescence emitted by 9,10-diphenyl-anthracene (or by p-terphenyl) in cyclohexane solution after photostimulation with Cerenkov radiation both grew-in and decayed more rapidly than when the solution was pulse-radiolysed (see Fig. 34). The delay in the formation of the aromatic excited state ( 0.5 ns) was attributed to the slowness of charge capture and of diffusion together of ions to form an excited state (Sect. 3.4). 

Cyclic voltammetry is a very valuable tool to use in following the course of redox reactions. An instructive demonstration of this is provided by studies on the oxidation of 9,10-diarylanthracenes in CH2C12—CF3C02H which can be considered to be nucleophile poor [81]. The use of CV in these studies is exemplified by Fig. 6. The first voltammogram [Fig. 16(a)] was recorded before bulk electrolysis was started. Peaks Ot and 02 correspond to the 1 e oxidations of 9,10-diphenyl-anthracene (DPA) and... 

Rigaudy, J., Scribe, P., Breliere, C., Photochemical Transformations of Endoperoxides Derived from Polycyclic Aromatic Hydrocarbons. 1. Case of the Photooxide of 9,10 Diphenyl Anthracene Synthesis and Properties of the Diepoxide Isomer, Tetrahedron 1981, 37, 2585 2593. 

Cyclovoltammetry (cv) is a simple method that provides useful information about an electrochemical conversion [8], This is illustrated by the cv of 9,10-diphenyl-anthracene (1) (Fig. 1 and Eq. 1). 

Cobalt(III) acetate oxidizes thianthrene and 9,10-diphenyl-anthracene in acetic or trifluoroacetic acid to the cation radicals, as shown by esr (Heiba et al., 1969b). In flow systems, Co(III) acetate in trifluoroacetic acid has also given well-resolved esr spectra of polyalkylbenzene cation radicals (hexa-, penta-, and all tetra-methylbenzenes, 1,3,5-tri-t-butyl-, and 1,4-di-t-butylbenzene) which are difficult to make in other ways (Dessau et al., 1970). When similar oxidations of alkylaromatics are carried out in static systems, further reactions occur, and these are sometimes of preparative value, since among the products are nuclear and side chain acetates. The reactions have been clarified most recently by the work of Heiba and Dessau. 

The analogies which exist between anodic oxidation and cathodic reduction reactions of aromatic compounds are extensive radicals formed from radical cations by chemical reaction can be further oxidised by other radical cations, i.e. by an overall disproportionation mechanism. Thus the formation of trans 9,10-dihydroxy 9,10-diphenyl anthracene on the addition of water to a solution of 9,10-diphenyl anthracene... 

Quartz-distilled water was used throughout the work. Sodium acetate (Suprapur) and potassium peroxodisulfate (pro analysi) were products of Merck and were used as received. Polyoxyethylene(23)dodecanol (Brij-35) and polycyclic aromatic hydrocarbons were purchased from Aldrich and used without further puriflcation. A 0.010 M stock solution of 9,10-diphenyl-anthracene was prepared in ethanol and Wcis daily diluted to an appropriate concentration in the eluent. Nitrogen was of the purest grade available. 

Organic ECL luminophores include luminol (2,3-amino"-phthal"-hydrazide), ABEl (V-(4-amino"-butyl)-V-ethyl"-iso"-lumi"-nol), lucigenin (V,V -dimethyl-9,9-bisacridinium), 9,10-diphenyl"-anthracene (DPA), RUB (rubrene), diimides, and various other organic compounds. 

An example of an energy-deficient system is the 9,10-diphenyl"-anthracene (DPA) and A,A,A, A -tetra"-methyl"-p-phenylene"-diamine (TMPD) ECL system ... 

Also, when a terpolymer that consists of vinyl pyrrolidone, styrene that is -substituted with 9,10-diphenyl anthracene, and a flluorescein derivative of acrylamide, is irradiated with light, there is a viscosity increase... 

The diminution of electrode fouling in oxido-reductive mode is shown in Fig. 22. Other ECL systems were also examined and sonoelectrochemical enhancement was observed for luminol (3-aminophthalhydrazide). This system has been thoroughly studied for the detection of low concentrations of residual hydrogen peroxide in contact-lens cleaning solutions. The ECL intensity of 9,10-diphenyl-anthracene in sonicated DMF solutions was increased by factors of 20-30 depending on the concentration of the solutions, ultrasound power, and fre-quencyT Similar effects were observed from l,5-diphenyl-3-styrylpyrazoline, rubrene, 9,10-dimethyl-anthracene, and perylene. ... 

A related mechanism for chemiluminescence is called chemically initiated electron exchange luminescence (CIEEL). Here, electron transfer from a donor to an acceptor initiates a thermal reaction that releases enough energy to place one of the reactants in an excited state. One case studied by Schuster is shown in Eq. 16.76, where electron transfer initiates CO2I0SS. This is followed by back electron transfer, giving the excited state of 9,10-diphenyl-anthracene, which then emits. 

Diphenyl anthracene] C104 n-C4H9, i-C4H9 CH3CN, CfiHjNO ... 

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