Photochromic Quinones

Barachevsky, V. А.

doi:10.1007/0-306-46911-1_8

Cited by 11 publications

(10 citation statements)

References 20 publications

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“…Diarylethenes form one of the thermally irreversible photochromic families, which also include fulgides, arylbutadienes, and aryloxynaphthacenequinones . Because of the fatigue resistivity and easy accessibility to the specially designed compounds, diarylethenes have attracted much attention as molecular-level switches .…”

Section: Introductionmentioning

confidence: 99%

Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism¹^,²

et al. 2007

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A diarylethene possessing one [4]thiaheterohelicene and one benzothiophene, the latter with a chiral methoxymethoxyethyl group on its C-3 position, was proved to work as a switch of specific optical rotation at a wavelength at which both colored and colorless forms have no absorption in solution. The difference of the specific optical rotation was 1300 degrees between the open form and the photostationary state. The specific optical rotation of one of the isolated optically active major colored forms was -4680 degrees. The conversion to the colored form was 64%, and the diastereomeric excess of photocyclization was 47%.

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Section: Introductionmentioning

confidence: 99%

Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism¹^,²

et al. 2007

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“…In 1970s and 1980s the effect of the PAQ structure on the spectral properties and some switching characteristics were investigated. These results were summarized by Gerasimenko, [42] Sokolyuk (Poteleshchenko) et al, [43] Gritsan, [44] as well as Barachevsky [45,46] during the 1990s. The emergence of new applications for photochromic molecules over the past two decades and the associated challenges suggests to revisit periaryloxyquinones and take a fresh look at the capabilities and limitations of this class of photoswitches.…”

Section: Introductionmentioning

confidence: 93%

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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“…Fulgide family compounds are the subject of numerous publications, mainly due to their photochromic properties and applications in the synthesis of lignans [1,2]. From the fulgide-related compounds, fulgimides appear to be the most interesting for data storage applications because of their increased fatigue resistance, higher chemical stability compared to the parent fulgides and the possibility of functionalisation at the nitrogen atom.…”

Section: Introductionmentioning

confidence: 99%

Efficient BOP-mediated synthesis of fulgimides

Krawczyk

Madej

Maurin

et al. 2012

Comptes Rendus. Chimie

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Photochromic Quinones

Cited by 11 publications

References 20 publications

Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism¹^,²

Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism¹^,²

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

Efficient BOP-mediated synthesis of fulgimides

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Photochromic Quinones

Cited by 11 publications

References 20 publications

Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism1,2

Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism1,2

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

Efficient BOP-mediated synthesis of fulgimides

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Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism¹^,²

Chiral Helicenoid Diarylethene with Large Change in Specific Optical Rotation by Photochromism¹^,²