Intramolecular photocycloaddition of anthracene and benzene ring systems

Cao, Derong; Dobis, Silvia; Meier, Herbert

doi:10.1016/s0040-4039(02)01476-4

Cited by 7 publications

(6 citation statements)

References 2 publications

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Some time ago we found a seco-cyclo isomerism which is based on the reversible intramolecular [4π+4π]photocycloaddition of benzene rings to anthracene. [16] The utility of such a system depends strongly on clean switching processes in both directions. The photochemistry of anthracenes, however, contains several reaction types.…”

Section: Introductionmentioning

confidence: 99%

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Structure Determination of Photoproducts of Anthracenes with (Arylmethoxymethyl) Sidechains

et al. 2007

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Section: Introductionmentioning

confidence: 99%

“…[22][23][24][25][26][27] The switching process discussed here, is typical for anthracenes which have in 9-position a phenylmethoxymethyl sidechain with an electron-rich benzene ring. [16] We describe in this paper such compounds which bear methoxyphenyl and dimethoxyphenyl groups. a typical absorption between 300 and 410 nm.…”

Section: Introductionmentioning

confidence: 99%

Structure Determination of Photoproducts of Anthracenes with (Arylmethoxymethyl) Sidechains

et al. 2007

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“…Scheme 8 summarizes the possible reaction routes. 38,39 The dimerization to open-chained systems represents moreover the first step in the formation of polymers. Dimers and polymers are preferentially formed when highly concentrated solutions of B-A-B compounds are used.…”

Section: Anthracene-benzene Biplanemersmentioning

confidence: 99%

“…Dimers and polymers are preferentially formed when highly concentrated solutions of B-A-B compounds are used. 38,40 In diluted solutions (c o 3.3 Â 10 À3 mol L À1 ) in benzene, cyclic monomers are formed -often in quantitative yields. The shorter tether A-CH 2 -O-B does not permit the photocyclization.…”

Section: Anthracene-benzene Biplanemersmentioning

confidence: 99%

Optical switches with biplanemers obtained by intramolecular photocycloaddition reactions of tethered arenes

Meier

Cao

2013

Chem. Soc. Rev.

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The dimerization of anthracene by a [4π + 4π] cycloaddition is one of the oldest and best known reactions in photochemistry. In the series of tethered bichromophoric arenes, this reaction type could be extended to anthracene-naphthalene, naphthalene-naphthalene and recently even to anthracene-benzene and naphthalene-benzene systems. Cyclophanes, which can be regarded as twofold or multiple tethered systems, are not discussed here. The cycloisomerizations are performed by irradiation at the long-wavelength absorption (λ > 270 nm), whereas shorter wavelengths (λ < 270 nm) lead to cycloreversions, which can be also achieved by a thermal route. The systems represent therefore a P- and T-type photochromism, which can be used for optical or chiroptical switches. An acceleration of the switch is possible by a singlet energy transfer (light harvesting antenna effect) in dendritic compounds. In the past 5 to 10 years many applications of these switches were studied in the context of photonic devices, sensor techniques, lithographic processes, imaging techniques, data processing and data storage.

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“…18,19 The most extensive investigations of benzene higher order cycloadditions are the intramolecular cycloadditions of alkoxy-substituted benzenes with naphthalene and anthracene that yield products like 25. 20,21 The work by Gilbert (Scheme 2) utilized 254 nm lamps and wavelengths down to 220 nm (Vycor filter), whereas in this work light above 290 nm (Pyrex filter) was used. In these new examples, the light is presumably directed largely into the 2-pyridone (k maz = 305 nm) whereas of the tethered substituted benzenes have absorptions mostly below the Pyrex cutoff.…”

Section: Introductionmentioning

confidence: 99%

Photo-[4+4]-cycloaddition (para) of meta-substituted benzenes with 2-pyridones

Khatri

Vrubliauskas

Sieburth

2015

Tetrahedron Letters

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a b s t r a c tBenzene is unreactive as a photochemistry partner with 2-pyridone, however benzene substitution can allow for an efficient [4+4] (a k a, 'para') photocycloaddition. Productive substituents include alkoxy, cyano, ester, and trifluoromethyl, suggesting that inductively electron-withdrawing groups are sufficient, however a single fluorine substituent does not result in cycloaddition. When the product of this cycloaddition contains a conjugated system (e.g., an unsaturated ester) a secondary photocycloaddition can follow, forming triply bridged all-syn-[3]ladderane products.

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Intramolecular photocycloaddition of anthracene and benzene ring systems

Cited by 7 publications

References 2 publications

Structure Determination of Photoproducts of Anthracenes with (Arylmethoxymethyl) Sidechains

Structure Determination of Photoproducts of Anthracenes with (Arylmethoxymethyl) Sidechains

Optical switches with biplanemers obtained by intramolecular photocycloaddition reactions of tethered arenes

Photo-[4+4]-cycloaddition (para) of meta-substituted benzenes with 2-pyridones

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