ChemInform Abstract: SYNTHESIS AND PHOTOCHROMIC PROPERTIES OF PHENOXY DERIVATIVES OF ANTHRAPYRIDONE AND ANTHRAPYRIDINE

Gerasimenko, Yu. E.; Sokolyuk, N. T.; Pisulina, L. P.

doi:10.1002/chin.198341325

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“…Peri-annulation of rings A or B and 1,4-benzoquinone with pyridone and pyridine resulted in photoactive compounds: 6-phenoxyanthrapyridones para-15, 8-phenoxyanthrapyridone para-16, 9-phenoxynaphthacenepyridone para-9, as well as 6-phenoxy-and 8-phenoxyanthrapyridines para-17 and para-18, respectively. [59,66] Heterocyclic derivatives were also found to be photoactive: 9phenoxynaphthaceno [5,6-bc]pyran-2,8-dione para-8 a [67] and 9-phenoxy-10H-benzo[c]naphtho[1,2,3-mn]acridin-10-one 20. [68] Among pyrazoloanthrones [69] and pyrazolonaphtacenones, [70] Nacetylated derivatives 21 and 22 displayed the most pronounced photoswitching.…”

Section: Effect Of Annulation and Substitution On Switchabilitymentioning

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%

“…Moreover, an unexpected stability of some heteroannulated PAQ analogues was reported. PAQs 10, [59] 38, [59] and 39 [66] were switchable even in the alcohol solutions (Figure 14B). Surprisingly, photogenerated ana-10 was more stable in ethanol than in toluene upon irradiation.…”

Section: Reactivity Of Ana-isomersmentioning

confidence: 99%

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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ChemInform Abstract: SYNTHESIS AND PHOTOCHROMIC PROPERTIES OF PHENOXY DERIVATIVES OF ANTHRAPYRIDONE AND ANTHRAPYRIDINE

Abstract: Beschrieben wird die Synthese der N‐Acylaminoanthrachinone (II) sowie der Titelverbindungen (III) und (IV).

Cited by 1 publication

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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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