ChemInform Abstract: 1‐PHENOXYANTHRACHINON, EIN VERTRETER NEUER PHOTOCHROMER VERBINDUNGEN

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

doi:10.1002/chin.197120345

Cited by 1 publication

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the first time, this property was reported by Gerasimenko and coworkers. [40] They found, that irradiation of para-1 in alcohols as solvents did not result in colored species. In addition, continuous irradiation of benzene solution of para-1 resulted in quantitative conversion to 1-hydroxyanthraquinone 30 a (Scheme 5A).…”

Section: Reactivity Of Ana-isomersmentioning

confidence: 99%

“…Yellow crystals of the presented compounds become orange or reddish orange upon exposure to sunlight or UV light. [40,60] Unfortunately, no further information regarding this phenomenon has been reported. The extent of light penetration into bulk crystals depends mainly on extinction coefficients and this value can reach up to millimeters in the case of some diarylethenes.…”

Section: Switching In the Solid Statementioning

confidence: 99%

“…The light-induced phenomenon was discovered by Gerasimenko and coworkers in 1971 for the simplest 1-phenoxyanthraquinone, para-1 (Figure 2A). [40] Irradiation of para-1 with UV or violet light resulted in migration of the phenyl group from the oxygen atom in position 1 (α) to the adjacent carbonyl group in position 9 (meso) to give ana-substituted 9-phenoxy-1,10anthraquinone. [41] Para-1 and its derivatives display a positive photochromic behavior with absorbance of both isomers in the visible region (Figure 2A) and photochromism occurring in the solid state (yellow crystalline para-1 changes its color to orange under UV light [40] ).…”

Section: Introductionmentioning

confidence: 99%

See 2 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

View full text Add to dashboard Cite

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.

show abstract

Section: Reactivity Of Ana-isomersmentioning

confidence: 99%

Section: Switching In the Solid Statementioning

confidence: 99%