Photodimerization of phenanthrene-9-carbonitrile and methyl phenanthrene-9-carboxylate

Lewis, Frederick D.; Barancyk, Steven V.; Burch, Eric L.

doi:10.1021/j100185a029

Cited by 8 publications

(4 citation statements)

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“…Our interest in the photophysics and photochemistry of aromatic amides ,, led us to investigate a family of six N -arylbenzamides (Chart ) in which the size of the N -aryl group is increased from aniline to 2-aminoanthracene. By lowering the singlet and triplet energy of the N -aryl group, we hoped to determine whether the singlet and triplet states of benzamides are delocalized or whether they are localized on the benzoyl and aminoarene subunits.…”

Section: Introductionmentioning

confidence: 99%

Luminescence of N-Arylbenzamides in Low-Temperature Glasses

Lewis

Liu

1999

J. Phys. Chem. A

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The low-temperature luminescence of benzamide and six additional N-arylbenzamides has been investigated in a methyltetrahydrofuran glass. The luminescence of microcrystalline benzamide has also been studied. Assignments of the fluorescence and phosphorescence have been made on the basis of comparisons with the spectra of benzamide and the six aminoarenes and with the results of semiempirical ZINDO calculations for the amines and amides. This information was used to construct state-energy diagrams for the six amides. The 430 nm fluorescence of benzanilide and the amides derived from 4-aminobiphenyl and 4-aminodiphenylacetylene is assigned to a n,π* state having a relaxed geometry and localized on the benzoyl group. The structured fluorescence of the amides derived from 4-aminostilbene and 2-aminoanthracene is attributed to a delocalized π,π* singlet state. The amide derived from 2-aminophenanthrene displays dual fluorescence. The amides derived from 4-aminostilbene and 2-aminoanthracene are nonphosphorescent. The structured phosphorescence of the amides derived from the other aminoarenes is assigned to a π,π* triplet state similar to that for the aminoarene. These results serve to further elucidate the unusual luminescence properties of the benzamides in solution as well as in low-temperature glasses.

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Section: Introductionmentioning

confidence: 99%

Luminescence of N-Arylbenzamides in Low-Temperature Glasses

Lewis

Liu

1999

J. Phys. Chem. A

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“…Addition of Michler's ketone (MK) in the irradiation of 9-CP and furan reduced the yield of 2 which has been established to be formed through a singlet excimer. 13 Addition of isoprene almost completely quenched the formation of 1. These results indicated that the formation of 1 was attributed to the triplet state of 9-CP.…”

Section: Resultsmentioning

confidence: 95%

Synthesis of 9-cyanophenanthrene–furan and –benzene cyclodimers and their reversion

Noh¹,

Jeon²,

Jeong³

et al. 1999

J. Chem. Soc., Perkin Trans. 2

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“…The mechanism of the photodimerization of phenanthrene derivatives was well investigated by Lewis et al 17 Depending on the electron-withdrawing substituents at the 9-position of phenanthrene, they found three types of reactions. Methyl phenanthrene-9-carboxylate undergoes self-quenching and dimerization via normal excimer mechanism, N,N-dimethylphenanthrene fails to undergo either self-quenching or photodimerization and 9-cyanophenanthrene fails to undergo self-quenching and undergoes dimerization predominantly via excitation of a ground-state p-complex.…”

Section: Resultsmentioning

confidence: 99%

Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives

et al. 2010

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Intramolecular [2+2] photocycloaddition of aromatic chain imides possessing bis-phenanthrene moieties afforded straight and cross ring closure products. The ratio of cycloadducts was dependent on reaction time and temperature, which resulted in a reversal of regioselectivity. The reaction was proved to involve a retro cycloaddition. The cross ring closure products were formed predominantly in the early stage of the reaction at lower reaction temperature. In contrast, the straight ring closure products were predominant at higher reaction temperature with prolonged irradiation.

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Photodimerization of phenanthrene-9-carbonitrile and methyl phenanthrene-9-carboxylate

Cited by 8 publications

References 0 publications

Luminescence of N-Arylbenzamides in Low-Temperature Glasses

Luminescence of N-Arylbenzamides in Low-Temperature Glasses

Synthesis of 9-cyanophenanthrene–furan and –benzene cyclodimers and their reversion

Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives

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