Optical and Electrochemical Properties of Anthraquinone Imine Based Dyes for Dye‐Sensitized Solar Cells. Issue 4 (16th December 2015)

• Record Type: Journal Article
• Authors: Prinzisky, Christian; Meyenburg, Ingo; Jacob, Andreas; Heidelmeier, Benjamin; Schröder, Fabian; Heimbrodt, Wolfram; Sundermeyer, Jörg
• Is Part Of: European journal of organic chemistry. Issue 4(2016)
• Page Start: 756
• Page End: 767
• Publication Date: 2015-12-16
• Subjects: Dyes/pigments -- Sensitizers -- Solar cells -- Cyclic voltammetry -- Optical spectroscopy -- N, O ligands -- Quinones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501309
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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, and23 ) with different primary aromatic amines and, in the case of benzoacridinone7, 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 of1, 3, and5 have the 9‐amino‐1, 10‐anthraquinone or 1‐hydroxy‐9, 10‐anthraquinone imine core. Furthermore, aminoanthraquinone9 and phenoxazine10 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 –1 cm –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 of3 show suppressed segregation on mesoporous TiO2 and an almost pure molecule photoluminescence spectrum containing two main transitions. A new excitonic transition was found in the crystal form. Abstract : Ten anthraquinone and anthraquinone imine based dyes have been synthesized and characterized by XRD and electrochemical investigations as well as by optical and photoluminescence (PL) spectroscopy. The PL spectra show that crystal formation results in redshifted spectra and a strong polarization of the excitonic absorption spectra.