ChemInform Abstract: REARRANGEMENT OF PHENOXYNAPHTHACENEQUINONES IN THE PRESENCE OF PROTIC AND LEWIS ACIDS

Gerasimenko, Yu. E.; Poteleshchenko, N. T.; Romanov, V. V.

doi:10.1002/chin.198105160

Cited by 2 publications

(15 citation statements)

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“…[73] Substitution. The effect of various substituents in the rings A and B on the photoactivity and photostability was studied in numerous papers for: 2,4,5-amino-substituted anthraquinone PAQs, [74] 2-amino-substituted anthraquinone PAQs, [75,76] 3,4,5,8amino-substituted anthraquinone PAQs, [77] 2,4,5,8-oxy-substituted anthraquinone PAQs, [78] and 6-substituted naphthacenequinone PAQs. [60] The obtained substitution-switching relationships were not quantitative; however, they could be useful for choosing the appropriate switches for various applications.…”

Section: Effect Of Annulation and Substitution On Switchabilitymentioning

confidence: 99%

“…The effect of various substituents in the rings A and B on the photoactivity and photostability was studied in numerous papers for: 2,4,5-amino-substituted anthraquinone PAQs, [74] 2-amino-substituted anthraquinone PAQs, [75,76] 3,4,5,8amino-substituted anthraquinone PAQs, [77] 2,4,5,8-oxy-substituted anthraquinone PAQs, [78] and 6-substituted naphthacenequinone PAQs. [60] The obtained substitution-switching relationships were not quantitative; however, they could be useful for choosing the appropriate switches for various applications. Depending on the nature and position of the substituents, the derived PAQs could be photochromic or non-photochromic, and show irreversible isomerization and/or (photo)degradation and/or pronounced chemical instability due to hydrolysis (Figure 9).…”

Section: Effect Of Annulation and Substitution On Switchabilitymentioning

confidence: 99%

“…[52] Their considerable thermal stability allowed to obtain anaisomers in the crystalline state for some PAQ photoswitches (unfortunately, without X-ray crystallographic analysis), including ana-2 (as orange plates), [53] ana-6 (as bright orange plates), [57] ana-3 e (as dark red needles). [60] For the first two photoisomers, thermal bleaching upon melting was reported. However, in the case of ana-2, the bleached sample preserved its photochromism and could be isomerized again to ana-2.…”

Section: Thermal Stabilitymentioning

confidence: 99%

“…Secondary amines such as piperidine did not form corresponding adducts, however, they boost the hydrolysis of ana-isomers by water. [60,77] In this process, the amines could play the role of catalyst, because the corresponding adducts 32 should easily form the products 30.…”

Section: Reactivity Of Ana-isomersmentioning

confidence: 99%

“…[102] These two approaches exploiting either steric or electronic stabilization, could be used for generation of new stable PAQs. Moreover, please note that naphthacenequinone [95,96] and 2-or 4-acylamino-substituted [74,76] derivatives possess the best fatigue to hydrolysis. Stabilization of photoisomers by additional migrations.…”

Section: Reactivity Of Ana-isomersmentioning

confidence: 99%

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Revisiting Peri‐Aryloxyquinones: From a Forgotten Photochromic System to a Promising Tool for Emerging Applications

Lvov,

Klimenko,

Bykov

et al. 2023

Chemistry A European J

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Emerging applications of photochromic compounds demand new molecular designs that can be inspired by some long‐known yet currently forgotten classes of photoswitches. In the present review, we remind the community about Peri‐AryloxyQuinones (PAQs) and their unique photoswitching behavior originally discovered more than 50 years ago. At the heart of this phenomenon is the light‐induced migration of an aromatic moiety (arylotropy) in peri‐aryloxy‐substituted quinones resulting in ana‐quinones. PAQs feature absorbance of both isomers in the visible spectral region, photochromism in the amorphous and crystalline state, and thermal stability of the photogenerated ana‐isomer. Particularly noticeable is the high sensitivity of the ana‐isomer towards nucleophiles in solution. In addition to the mechanism of molecular photochromism and the underlaying structure‐switch relationships, we analyze potential applications and prospects of aryloxyquinones in optically switchable materials and devices. Due to their ability to efficiently photoswitch in the solid state, PAQs are indeed attractive candidates for such materials and devices, including electronics (optically controllable circuits, switches, transistors, memories, and displays), porous crystalline materials, crystalline actuators, photoactivated sensors, and many more. This review is intended to serve as a guide for researchers who wish to use photoswitchable PAQs in the development of new photocontrollable materials, devices, and processes.

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Section: Effect Of Annulation and Substitution On Switchabilitymentioning

confidence: 99%

Section: Effect Of Annulation and Substitution On Switchabilitymentioning

confidence: 99%

Section: Thermal Stabilitymentioning

confidence: 99%

Section: Reactivity Of Ana-isomersmentioning

confidence: 99%

Section: Reactivity Of Ana-isomersmentioning

confidence: 99%

See 3 more Smart Citations

Revisiting Peri‐Aryloxyquinones: From a Forgotten Photochromic System to a Promising Tool for Emerging Applications

Lvov,

Klimenko,

Bykov

et al. 2023

Chemistry A European J

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Revisiting peri-aryloxyquinones: From a forgotten photochromic system to a promising tool for emerging applications

Lvov,

Klimenko,

Bykov

et al. 2023

Preprint

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Emerging applications of photochromic compounds demand new molecular designs that can be inspired by some long-known yet currently forgotten classes of photoswitches. In the present review, we would like to remind the community about Peri-AryloxyQuinones (PAQs) and their unique photoswitching behavior originally discovered by Gerasimenko more than 50 years ago. At the heart of this phenomenon is the light-induced migration of an aromatic moiety (arylotropy) in peri-aryloxy-substituted quinones resulting in ana-quinones. PAQs feature absorbance of both isomers in the visible spectral region, photochromism in the amorphous and crystalline state, and thermal stability of the photogenerated ana-isomer. Particularly noticeable is the high sensitivity of the ana-isomer towards nucleophiles in solution. In addition to the mechanism of molecular photochromism and the underlaying structure-switch relationships, we analyze potential applications and prospects of aryloxyquinones in optically switchable materials and devices. Due to their ability to efficiently photoswitch in the solid state, PAQs are indeed attractive candidates for such materials and devices, including electronics (optically controllable circuits, switches, transistors, memories, and displays), porous crystalline materials, crystalline actuators, photoactivated sensors, and many more. This review is intended to serve as a guide for researchers who wish to use photoswitchable PAQs in the development of new photocontrollable materials, devices, and processes.

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ChemInform Abstract: REARRANGEMENT OF PHENOXYNAPHTHACENEQUINONES IN THE PRESENCE OF PROTIC AND LEWIS ACIDS

Abstract: Die p‐Chinone (I) gehen unter der Einwirkung von konz. H2SO4 oder AlCl3 (in Benzol) reversibel in Gemische mit den tautomeren ana‐Chinonen (II) über; in den Fällen (a) dominieren in den Gemischen die ana‐Isomeren (IIa), in den Fällen (b) die p‐Isomeren (Ib).

Cited by 2 publications

References 0 publications

Revisiting Peri‐Aryloxyquinones: From a Forgotten Photochromic System to a Promising Tool for Emerging Applications

Revisiting Peri‐Aryloxyquinones: From a Forgotten Photochromic System to a Promising Tool for Emerging Applications

Revisiting peri-aryloxyquinones: From a forgotten photochromic system to a promising tool for emerging applications

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