ChemInform Abstract: Synthesis and Arylotropic Properties of 11‐Aryloxy‐6‐amino‐5,12‐naphthacenequinones.

Abstract

285ChemInform Abstract The interchange between the 11-aryloxy-5,12-quinones (III) and the 12-aryloxy-5,11-quinones (IV) is dependent on the wavelength of the irradiation. Irradiation with λ = 300-480 nm effects formation of (IV), whereas on irradiation with λ > 510 nm (III) is recovered from (IV). Treatment of (III) with conc. H2SO4 affords (IV) as well.

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

“…Importantly, annulation that does not contribute to the central 1,4‐quinone motif in PAQs prevents their switchability. Thus, the presence of an additional benzene ring as peri‐ annulating motif makes the isomerization thermodynamically unfavored and results in photoinactive compounds 23 and 24 [71] . The same result was reported for isoxazole‐based derivative 25 [72] .…”

“…Afterwards, related compounds comprised of only one carbonyl in the switching chromophore were investigated (Figure 8). 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: 9‐phenoxynaphthaceno[5,6‐ bc ]pyran‐2,8‐dione para‐ 8 a [67] and 9‐phenoxy‐10 H ‐benzo[ c ]naphtho[1,2,3‐ mn ]acridin‐10‐one 20 [68] .…”

“…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: 9‐phenoxynaphthaceno[5,6‐ bc ]pyran‐2,8‐dione para‐ 8 a [67] and 9‐phenoxy‐10 H ‐benzo[ c ]naphtho[1,2,3‐ mn ]acridin‐10‐one 20 [68] . Among pyrazoloanthrones [69] and pyrazolonaphtacenones, [70] N ‐acetylated derivatives 21 and 22 displayed the most pronounced photoswitching.…”

“…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.…”

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

“…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.…”