Polyphenylnaphtalenes, especially 1,4,5,8-tetraphenylnaphthalene

Bergmann, Ernst D.; Blumberg, S.; Bracha, Perez; Epstein, S.

doi:10.1016/s0040-4020(01)93208-9

Cited by 28 publications

(6 citation statements)

References 36 publications

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“…The ultraviolet spectrum of 10 (Xmax of the longest wavelength band, 335 nm) displays a blue shift relative to anthracene (376 nm) whereas 9,10-diphenylanthracene displays a red shift (392 nm). This is consistent with 1,2,3,4-tetraphenylnaphthalene (296 nm) and 1,4,5,8-tetraphenylnaphthalene (1) (334 nm) which exhibit blue and red shifts, respectively, relative to naphthalene (312 nm). marie acid formed no adduct.…”

supporting

confidence: 85%

Derivatives of hexaphenylisobenzofuran

Razmara¹,

Stevens²

1972

J. Chem. Eng. Data

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to give a yield of 64%. Pure product, mp 174-5°C , was obtained by two successive recrystallizations from propanol, charcoal being used in the last recrystallization. About 50 ml of solvent per gram of product was necessary. Benzene was also a satisfactory recrystallization solvent. E. Transesterification Attempt. Dimethyl tetrachloroterephthalate, 25 grams (0.075 mole), was dissolved in a solution of 135 ml n-propanol, 35 ml benzene, and 2 grams ptoluenesulfonic acid. Intermittent heating and reflux over 8 days were accompanied with the addition of 60 ml benzene, 20 ml propanol, and acid (3 X 0.5 gram). Crystals obtained upon cooling were starting material, mp 157-8.5°C. Two additional crops from the reaction mixture were substantially the dimethyl ester.Comparable attempts at transesterification with sodium propoxide and titanium isopropoxide as catalysts also failed. F. ' Attempted Saponification. A mixture of 1 gram (0.003 mole) dimethyl tetrachloroterephthalate, 75 ml absolute ethanol, and 25 ml of 0.44ÍV KOH was refluxed 3 hr. After it cooled, 50 ml of water and 25 ml of 0.LV HC1 were added. Titration, using O.liV HC1, to the phenolphthalein end point gave a neutralization equivalent, after blank correction, of 242 (theory is 166). The same procedure was used, and a saponification equivalent for di-n-propyl tetrachlorophthalate of 197 was found (caled 194). Longer time and variants of this procedure with aliphatic tetrachloroterephthalates still did not give a satisfactory saponification equivalent. Substantially more drastic treatment resulted in an attack on the aromatic nucleus. Profit and Timm (10) do not report such an attack in their saponification procedure.G. Complexation Studies. Previously described procedures did not give complexes of hexamethylbenzene with aliphatic tetrachloroterephthalates as were obtained with tetrachlorophthalate and tetrabromophthalate esters (8). With dimethylaniline, colors were observed with dipropyl (pale yellow), dibutyl (pale yellow), dioctyl (greenish yellow), and bis-pentafluorophenyl (dark yellow) tetrachloroterephthalates. Other observations are reported in the discussion.H. Infrared Spectra. All were taken at 0.66% concentration in KBr pellets.I. Elemental Analyses. All were made by Spang Microanalytical Laboratories of Ann Arbor, Mich. Analyses were in satisfactory agreement with calculated values and were made available to reviewers.LITERATURE CITED

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supporting

confidence: 85%

Derivatives of hexaphenylisobenzofuran

Razmara¹,

Stevens²

1972

J. Chem. Eng. Data

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“…Ph Ph XIV possible between the ring and phenyl substituents. A recent study (78) of some phenylnaphthalenes has indicated similar bathochromic shifts (Table II). For example, the spectrum of 1,4,5,8-tetraphenylnaphthalene (XV) is highly reminiscent of those of 1,4,9,10tetraphenylanthracene (XIV) and rubrene (XVI), but entirely different from that of terylene (XVII)…”

Section: IImentioning

confidence: 56%

“…Overcrowding due to extensive substitution also results in considerable loss of fine structure. Several illustrations of this type are available (19,50,78,161,221,269,430) from studies on alkyl-and arylnaphthalenes. Dianov and Chernova (161) have found that a larger bathochromic shift occurs with 1,4,5,8-tetramethylnaphthalene than for the all ß-substituted 2,3,6,7 isomer, particularly in the region µ.…”

Section: IImentioning

confidence: 99%

peri Interaction in Naphthalene Derivatives

1966

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“…The latter are derived from sensitized oxidation experiments in which methanol solvent was used in order to have a reliable value of the sensitizer triplet yield. The determinations of > from which ksox is derived, were made both in benzene and in methanol with results which were nearly identical except in the case of DPDMI (see 6.13 (M) 5.24 (M) 6.62 (M) 6.88 (M) 0 In benzene solution, except values marked (M) which are in methanol. 6 1,3-Diphenylisobenzofuran.…”

Section: Resultsmentioning

confidence: 93%

“…The determinations of > from which ksox is derived, were made both in benzene and in methanol with results which were nearly identical except in the case of DPDMI (see 6.13 (M) 5.24 (M) 6.62 (M) 6.88 (M) 0 In benzene solution, except values marked (M) which are in methanol. 6 1,3-Diphenylisobenzofuran. ' l,3-Diphenyl-5,6-dimethylisobenzofuran.…”

Section: Resultsmentioning

confidence: 93%

Photooxidation of isobenzofurans. Dual mechanism process

Olmsted¹,

Akashah²

1973

J. Am. Chem. Soc.

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The photooxidation of several substituted isobenzofurans has been studied. Kinetic behavior at low substrate concentrations shows that a second mechanism other than that involving singlet oxygen is operative, and the absence of azulene quenching demonstrates that the second mechanism involves direct addition of oxygen to excited singlet isobenzofuran. Rate constants for this singlet substrate-ground state oxygen reaction are in the range of 10 M_1 sec-1 and the mechanism is calculated to contribute about 10% of the photooxidation at high isobenzofuran concentration, ranging upward to virtually 100% at lower substrate concentrations. The mechanism is suggested to be via charge-transfer rather than concerted addition and the possibility of such an oxidation mechanism is generalized to other aromatic systems.A great deal of evidence has been amassed in the past few years to indicate that photoinduced addition of molecular oxygen to several types of substrates proceeds primarily if not exclusively via excited oxygen molecules in the (^g) electronic state.2

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Polyphenylnaphtalenes, especially 1,4,5,8-tetraphenylnaphthalene

Cited by 28 publications

References 36 publications

Derivatives of hexaphenylisobenzofuran

Derivatives of hexaphenylisobenzofuran

peri Interaction in Naphthalene Derivatives

Photooxidation of isobenzofurans. Dual mechanism process

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