Optical and Electrochemical Properties of Anthraquinone Imine Based Dyes for Dye‐Sensitized Solar Cells

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, and 23) with different primary aromatic amines and, in the case of benzoacridinone 7, by a subsequent photoinduced 6π 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-

Influence of TiO2 Nanoparticles on Liquid Crystalline, Structural and Electrochemical Properties of (8Z)-N-(4-((Z)-(4-pentylphenylimino)methyl)benzylidene)-4-pentylbenzenamine

“…Currently, a lot of new imines with various symmetries are synthesized to be used as thermal, biological or liquid crystalline materials [5,6,7,8]. Moreover, some imines are tested in organic devices, such as solar cells [9,10,11,12,13,14].…”

An Experimental and Theoretical Study of Dye Properties of Thiophenyl Derivatives of 2-Hydroxy-1,4-naphthoquinone (Lawsone)

“…The latter can be achieved by incorporating different polar functional groups in the structure of sensitizer (as carboxylic acid, amines, ketones, among others). Prinzisky et al studied the performance of a hydroxy-anthraquinone imine as a dye for DSSCs [ 51 ], where the hydroxyl and imine groups acting anchoring the molecule to the TiO 2 semiconductor surface. Recently, Sreeja and Pesala studied the performance of natural dyes indigo, lawsone, and betanin as co-sensitizer for solar cells [ 23 ].…”

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…As part of their research on anthraquinone imine dyes for DSSCs, Sundermeyer and co-workers reported in 2016 a four-step synthesis of benzoacridinone 191.3 ( Scheme 191 ). 371 The requisite precursor 191.1 had to be obtained via a monoacetal intermediate, to avoid selectivity problems. 191.1 was then photolyzed in a Mallory-type reaction, yielding 191.3 .…”