This comprehensive review, covering the years 1968–2022, is not only a retrospective investigation of a certain group of linearly fused aromatics, called acenes, but also a presentation of the current state of the knowledge on the synthesis, reactions, and applications of these compounds. Their characteristic feature is substitution of the aromatic system by one, two, or three organophosphorus groups, which determine their properties and applications. The (PIII, PIV, PV) phosphorus atom in organophosphorus groups is linked to the acene directly by a P-Csp2 bond or indirectly through an oxygen atom by a P-O-Csp2 bond.
Light-triggered antimicrobial cellulose surfaces were obtained by the immobilization of a photosensitive phenosafranin dye (PSF) in a hybrid organic–inorganic silsesquioxane polymer applied on handsheets prepared from a standard bleached softwood pulp. These coatings were deposited by polycondensation of methyltriethoxysilane and an alkoxysilyl derivative of phenosafranin (TESPSF) obtained by the thiolene addition reaction and coupling of the succinic anhydride derivative with a primary amine group of PSF. TESPSF and coatings were characterized by advanced techniques in terms of chemical structure (1H, 13C, 29Si NMR, MS, ATR-IR), surface properties (SEM, EDX, water contact angles), and optical properties (UV, reflection light intensity, ISO brightness). The light-induced antimicrobial activity of sheets of paper coated with new materials showed the inhibition of the growth of the bacteria Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 8739. The cytotoxicity studies of modified cellulose surfaces were performed using erythrocyte lysis assays under both dark and light conditions exhibited no toxicity on erythrocytes. Thus, the new material did not reveal harmful effects on erythrocytes, regardless of the presence and absence of light.
The reaction of (ortho-acetalaryl)arylmethanols with various phosphines PR1R2R3 (R1 = R2 = R3 = Ph; R1 = R2 = Ph, R3 = Me and R1 = R2 = Me, R3 = Ph) under acidic conditions (e.g., HCl, HBF4, TsOH) unexpectedly led to the formation of (10-hydroxy-9,10-dihydroanthr-9-yl)phosphonium salts instead of the corresponding anthryl phosphonium salts. The cyclization occurred according to the Friedel–Crafts mechanism but without the usually observed Bradsher dehydration, giving cyclic products in the form of cis/trans isomers and their conformers. In case of electron-rich and less-hindered dimethylphenylphosphine, all four stereoisomers were recorded in 31P{1H} NMR spectra, while for the other phosphines, only the two most stable cis/trans stereoisomers were detected. This study was supported by DFT and NCI calculations in combination with FT-IR analysis.