35897-82-6Relevant articles and documents
A Green-Absorbing, Red-Fluorescent Phenalenone-Based Photosensitizer as a Theranostic Agent for Photodynamic Therapy
Kaye, Esther G.,Kailass, Karishma,Sadovski, Oleg,Beharry, Andrew A.
, p. 1295 - 1301 (2021)
Phenalenone is a synthetically accessible, highly efficient photosensitizer with a near-unity singlet oxygen quantum yield. Unfortunately, its UV absorption and lack of fluorescence has made it unsuitable for fluorescence-guided photodynamic therapy against cancer. In this work, we synthesized a series of phenalenone derivatives containing electron-donating groups to red-shift the absorption spectrum and bromine(s) to permit good singlet oxygen production via the heavy-atom effect. Of the derivatives synthesized, the phenalenone containing an amine at the 6-position with bromines at the 2- and 5-positions (OE19) exhibited the longest absorption wavelength (i.e., green) and produced both singlet oxygen and red fluorescence efficiently. OE19 induced photocytotoxicity with nanomolar potency in 2D cultured PANC-1 cancer cells as well as light-induced destruction of PANC-1 spheroids with minimal dark toxicity. Overall, OE19 opens up the possibility of employing phenalenone-based photosensitizers as theranostic agents for photodynamic cancer therapy.
Ligand mixed-valence and electrical conductivity in coordination complexes containing a redox-active phenalenol-substituted ligand
Dale, Sarah,Bonanno, Nico M.,Pelaccia, Mark,Lough, Alan J.,Miyawaki, Atsuhiro,Takahashi, Kazuyuki,Lemaire, Martin T.
, p. 8053 - 8056 (2019)
A new redox-active hydrazone ligand bearing a phenalenol group is described (phpl), which produces neutral six-coordinate Fe and Co complexes (1 & 2) with the ligands identified in different oxidation states; an open-shell anion radical and closed-shell dianion. An intense and very low-energy intervalence charge transfer (IVCT) band is identified in solid-state and in solution in the complexes. Single crystals of 1 are semiconducting (at 300 K, σ = 3.05 × 10-4 S cm-1 with Ea = 245 meV).
1,9-Disubstituted phenalenes-I. Synthesis of n- and s-derivatives of 9-hydroxy-1-phenalenone
Franz,Martin
, p. 2147 - 2151 (2007/10/06)
The reaction of 9-hydroxy-1-phenalenone with Ag2O and alkyliodides gives the analogous β-keto-ethers from which synthetic pathways have been devised to isolate and characterise some nitrogen and sulphur derivatives. As intermediates stable phenalenium cations can be isolated by the reaction of 9-substituted 1-phenalenones with [(C2H5)3O]+BF4-. Whenever possible, a strong intramolecular H-bond is formed between the 1-and 9-substituents as shown by the low-field resonances of the respective hydrogens in the 1H NMR and the stability of the compounds towards reduction.
