1629-56-7Relevant academic research and scientific papers
Anthraphen: A Salphen-Like Non-Innocent Tetradentate Anthraquinone Imine Dye - Coordination and Electrochemistry
Prinzisky, Christian,Jacob, Andreas,Harrer, Marcus,Elfferding, Michael,Sundermeyer, J?rg
, p. 477 - 489 (2016)
A new, highly redox-active chromophore ligand, H2(anthraphen) (1), containing two o-phenylenediamine-linked anthraquinone imine units has been synthesized in a three-step synthesis and fully characterized by X-ray crystallography, UV/Vis spectroscopy, and cyclic voltammetry. The dark-red dye 1 shows molar extinction coefficients of up to 47000 L mol-1 cm-1 and four reversible reduction processes. This dianionic N2O2 ligand, with a significantly extended π system, offers a salphen-like binding cavity for metal coordination, as has been demonstrated by the synthesis of [K2(anthraphen)] (2) and the transition-metal complexes of TiIV (3), VIV (4), FeII (5), FeIII (6), CoII (7), NiII (8), CuII (9), PdII (10), PtII (11), and ZnII (12). These metal chromophores have colors ranging from dark-red, violet, green to black. Their optical and electrochemical properties were investigated and compared with those of the diprotic ligand. Coordination led to an increase in the molar extinction coefficients up to 66400 L mol-1 cm-1 in the case of [V(anthraphen)O] (4), broadening of the absorption bands in the visible-light region as well as a redshift of the lowest-energy absorption band. The lowest-energy absorption observed for these complexes to date is for [Ni(anthraphen)] (8) at 784 nm. The metal chromophores exhibit up to five fully reversible oxidation and reduction processes.
Optical and Electrochemical Properties of Anthraquinone Imine Based Dyes for Dye-Sensitized Solar Cells
Prinzisky, Christian,Meyenburg, Ingo,Jacob, Andreas,Heidelmeier, Benjamin,Schr?der, Fabian,Heimbrodt, Wolfram,Sundermeyer, J?rg
, p. 756 - 767 (2016)
A number of anthraquinone imines (1–3, 5–8) and an anthrone diamine (4) have been synthesized by the condensation of 9,9-dimethoxy-10-anthrone derivatives (13, 18, and 23) with different primary aromatic amines and, in the case of benzoacridinone 7, by a subsequent photoinduced 6 electrocyclization. All the compounds were fully characterized by UV/Vis spectroscopy, cyclic voltammetry, and X-ray diffraction. The XRD analyses proved that the preferred tautomers of 1, 3, and 5 have the 9-amino-1,10-anthraquinone or 1-hydroxy-9,10-anthraquinone imine core. Furthermore, aminoanthraquinone 9 and phenoxazine 10 were synthesized by the reaction of 1-amino-9,10-anthraquinone with 3,5-di-tert-butylphenyl-o-benzoquinone, which led to dyes with high molar extinction coefficients of up to 101600 L mol–1cm–1. In addition, the absorption maxima of the 1-hydroxy-9,10-anthraquinone imines appear in the range of 246 and 591 nm, at variance with the absorption maxima of the parent 1-hydroxy-9,10-anthraquinone. The cyclic voltammograms of all the compounds show multiple redox processes. In addition, the optical absorption and photoluminescence spectra of 3 show suppressed segregation on mesoporous TiO2and an almost pure molecule photoluminescence spectrum containing two main transitions. A new excitonic transition was found in the crystal form.
An efficient synthesis of 9-anthrone lactone derivatives via the Knoevenagel condensation and intramolecular cyclization
Gao, Liming,Guan, Jing,Lyu, Lili,Ma, Mingliang,Shan, Bin,Tan, Weiqiang,Xia, Yan,Yang, Qipeng,Zhan, Xiuzhi,Zheng, Jifang
, (2020)
One-step synthesis of 9-anthrone lactone derivatives from 1-acetyloxyanthraquinone with a variety of dicarbonyl substrates in the presence of K2CO3 by Knovenagel condensation and intramolecular cyclization is developed. Possible reaction mechanisms have been investigated using the density functional theory (DFT), which has been widely used in the study of reaction mechanism. The strategy could be useful for the synthesis of the core structure of marine natural product aspergiolide.
