2,2′‐<i>P</i>‐phenylenebis(4‐methyl‐5‐phenyloxazole) and other solutes for scintillation counting

Walker, D.G.; Waugh, Thomas D.

doi:10.1002/jhet.5570010203

Cited by 8 publications

(3 citation statements)

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“…In toluene, too low for suitable evaluation of the compound as a primary liquid scintillation solute. The Introduction of the relatively small methyl group into the 4-position of the oxazole ring markedly increases the solubility, however, an observation also made by Walker and Waugh for other oxazole compounds (10).…”

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confidence: 78%

“…Walker and Waugh also observed in a study on 2,2'-pphenylenebis(4-methyl-5-phenyloxazole) (dimethyl POPOP) that substitution of a methyl group Into the 4posltlon of the oxazole ring caused a bathochromic shift of 5 nm for the fluorescence maximum when compared with the unsubstituted POPOP. Also, they reported an 11-nm bathochromic shift in the fluorescence maximum for 4-methyl-2,5-dlphenyloxazole (376 nm) when compared to 2,5-diphenyloxazole (365 nm) (10). Compound If, which has a methyl substituent in the 4-posltion of the oxazole ring, likewise shows a bathochromic shift of 9 nm of the fluorescence maximum when compared to the value of 401 nm reported for la by Hansbury et al (4).…”

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confidence: 98%

“…This RPH value probably is close to the maximum obtainable for If, even at higher concentrations, in view of the value of 0.94 for Id, which was obtained at a concentration of 10.8 g/l. Although placing an alkyl group in the 4-position of the oxazole ring can bring about a bathochromic shift in the emission spectrum, it does not appear to markedly improve the scintillation performance (10).…”

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confidence: 99%

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Scintillation properties of alkyl and alkoxy derivatives of 5,5'-diphenyl-2,2'-bioxazole

Taber¹,

Grantham²,

Binkley³

et al. 1973

J. Chem. Eng. Data

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Several alkyl and alkoxy derivatives of the 5,5'-diphenyl-2,2'-bioxazole (POOP) system were synthesized and were good primary liquid scintillation solutes. The absorption and fluorescence characteristics are reported and discussed.Previous investigations by Hayes and his coworkers (5. 6) of compounds which might prove suitable as primary and secondary liquid scintillation solutes indicated that 5,5'-diphenyl-2,2'-bioxazole (POOP) (la) was a good scintillator, but its performance was hampered by its limited solubility in the solvent employed, toluene. Compound la, at a concentration of just 1.0 g/l., was reported to have a maximum pulse height of 0.76 relative to a 3.0 g/l. solution of PPO in toulene. In view of this excellent scintillation performance at relatively low concentration, we decided to synthesize a number of alkyl and alkoxy derivatives of POOP in an attempt to improve the solubility and thus the scintillation performance of this compound. Those compounds prepared and evaluated in this study are listed in Table I . 0 0 Q-"-cH2-cH3 -+ @ ! -c H --C H J I -, Br I1 0 0 II @-CH-N I /cn \ C -CH3 I 1 0 I11 0 @ ! -c H -N H a + c l -I -CH, nr 0 0 0 0 e!! -CH-xH-c II -c I 1 -m-c H -c 1 ' -+ If I CH I CH V ' To whom correspondence should be addressedThe synthesis of each of the compounds was accornplished by first brominating the appropriate substituted acetophenone or propiophenone followed by a Gabriel synthesis to the amine salt (IV) and a reaction of I V with oxalyl chloride in pyridine to give the amide V. Cyclization of V to the POOP derivatives Ib-If was accomplished with phosphorous oxychloride as described by Walker and Waugh (70). R3 Ia, R, = R, = R3 = H b, Rl = R3 = H, R, = -OCH3 C, R1 = R3 = H: R, d. R, = R3

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confidence: 98%

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confidence: 99%

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Scintillation properties of alkyl and alkoxy derivatives of 5,5'-diphenyl-2,2'-bioxazole

Taber¹,

Grantham²,

Binkley³

et al. 1973

J. Chem. Eng. Data

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Zur Darstellung von Bioxazolylen‐(2.2′) und Bithiazolylen‐(2.2′) sowie von Arylen‐bis ‐oxazolyl‐(2)‐ und Arylen‐bis‐thiazolyl‐(2)‐Derivaten

Heınze

Baumgärtel

1970

Chem. Ber.

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Durch IJmsctzung WJI Desylan~inhydrochlorid mit Carbons~urechloriden bzw. init Dicarbonsauredichloriden gelangt man zu mu-Acylamino-desoxybenzoinen (2a, b) bzw. zu N.N'-Bis-desyl-dicarbonsaurediamiden (2c ~ f). Diese lassen sich mit Phosphorpentachlorid zu Oxazolderivaten 3, mit Phosphorpentasulfid zu Thiazolderivateii 4 kondensieren. Heinzr und Bauingartei Jahrg. 103 N.N'-Bis-fu-phenyl-phennc-vl ~-biphen,vl-dicarbonsar~re-(4.4')-diarnid (Ze) : 6.00 g (21.4 n~Mol) Biphcnyl-dicurho~~saurc-(4.4')-dirl~/orid in 300 ccm trockenem Benzol ergebcn niit 12.0 g (48.5 mMol) I und 75 ccm f'yridin analog 2d 11.0 g (17.5 mMol -82"4,) farbloses Kristallpulver. Schmp. 267--268". v i~. .~ 3330, vc,-c) 1685, Amid I 1632, 1652/cm. C121431NZ04 (628.7) Ber. C 80.23 H 5.13 N 4.43 Cef. C 80.12 H 5.05 N 4.31 N.N"-Bisicr -pheii?;l-plieiiric,vli -p-trrplien~~l-dicrrrbun.~iii~~e-(4.4") -dinmid (2f): 8.00 g (24.2 mMol) p-Trrphen~l-dictrrhutisuiire-i4.4"~-~i~l1i~~ri~ in 400 ccm trockenem Benzol ergeben rnit 12.0 g (48.5 mMol) 1 trnd 100 ccni Pjridiir annlog 2d 15.7 g (22.3 mMol ~~-99",;) furbloses Kristdllpulver. Schnip. 287 --289'.

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Nitrogen heterocyclic analogs of polyaryls

Buu‐Hoï

Périn

1965

Journal of Heterocyclic Chem

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Nitrogen heterocyclic analogs of polyaryls, derived from pyridine, quinoline, benzo[h]quinoline, indole, indolizine, and imidazo[l, 2-alpyridine, have been prepared from 1,4diacetyl-and 1,3,5-triacetylbenzene and 2,6-diacetylpyridine, for study of their physical, chemical and biological properties.Polyaryls a r e of interest as scintillators in liquid scintillation counters used in nuclear physics, and some of their heterocyclic analogs, especially 2,2'pphenylenebis( 5phenyloxazole) (POPOP) and its homologs, have also been employed with success for that purpose (1). In biology, one polyaryl, v i z . 1,3,5-tri-p-xenylbenzene (I), has been found to be carcinogenic, producing, on skin-painting in mice, not only epitheliomas in situ but also tumors of the liver (2); earlier, another polyaryl, 1,3,5-triphenylbenzene, had also been reported as carcinogenic (3) but this claim could not be confirmed later (4).Further, in our laboratory we are interested in investigating the behavior of polyaryls and their nitrogen heterocyclic analogs in Rayleigh light diffusion studies, as a means of determining electron delocalization in these molecules (5). These various interests led us to synthesize a number of nitrogencontaining analogs of polyaryls which include in their molecule the following heterocycles: pyridine, quino-The intermediates used were three polyketones:1 , 4diacetylbenzene, 1 , 3 , 5triacetylbenzene, and 2,6 -diacetylpyridine. In the indole group, 1,4diacetylbenzene, heated with phenylhydrazine, gave a bisphenylhydrazone which could be cyclized with either zinc chloride o r polyphosphoric acid to the pentacyclic 1,4-di-(2-indolyl)benzene (II); replacement of phenylhydrazine by pxenylhydrazine afforded the heptacyclic 1,4-di-(5-pheny1-2-indolyl)benzene (III). The bisphenylhydrazone and bis-ptolylhydrazone of 2,6-diacetylpyridine were cyclized by polyphosphoric acid to 2,6-di-(2-indolyl)pyridine ( N ) and 2,6-di-(5-methyl-2-indolyl)pyridine (V) respectively. Interestingly, these two compounds gave monopicrates with picric acid, which suggests that the heterocycle involved in this complex formation was the pyridine one rather than the indole one. 1,3,5-Triacetylbenzene readily gave trisarylhydrazones on heating a t 180' with phenyl-and p-tolylhydrazine, but not when the usual procedure for the preparation of hydrazones (use of arylhydrazine salts in ethanol) was employed; indolization, effected with polyphosphoric acid, furnished 1,3,5-tri-(2-indolyl)benzene (VI) and 1,3,5-tri-( 5 -methyl -2 -indoly1)benzene (VE) respectively. It is interesting to note that compound VI gave with tetrachlorophthalic anhydride a staale charge-transxx coinpiex (b) made up of three molecules of the electron acceptor for one molecule of the electron donor; this indicates that the three indole nuclei behave here as separate units in the charge-transfer phenomenon with the halogenated anhydride.In the quinoline series, a Pfitzinger reaction performed on one mole of 1,3,5-triacetylbenzene and 3 moles of isatin readily afforded "tri-atophan" (...

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2,2′‐P‐phenylenebis(4‐methyl‐5‐phenyloxazole) and other solutes for scintillation counting

Abstract: The advent of large liquid scintillation counters has created a need for a secondary solute which is more soluble in organic solvents than is 2,2'-P-phenylenebis(5-phenyloxazole) (POPOP, I or 11, R-substituents = H), the preferred secondary solute for smallscale work.

Cited by 8 publications

References 5 publications

Scintillation properties of alkyl and alkoxy derivatives of 5,5'-diphenyl-2,2'-bioxazole

Scintillation properties of alkyl and alkoxy derivatives of 5,5'-diphenyl-2,2'-bioxazole

Zur Darstellung von Bioxazolylen‐(2.2′) und Bithiazolylen‐(2.2′) sowie von Arylen‐bis ‐oxazolyl‐(2)‐ und Arylen‐bis‐thiazolyl‐(2)‐Derivaten

Nitrogen heterocyclic analogs of polyaryls

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