Meso-substituted 21,23-dithiaporhyrins were synthesized that self-assemble into columnar liquid crystalline phases. Furthermore, the porphyrins possess absorption profiles that span from 400 nm to 800 nm, undergo two reversible electrochemical redox reactions at approximately 465 and 670 mV vs. ferrocene/ferricenium and are electrochromic. Thin films of these dithiaporhyrins of approximately 60 nm thickness were formed by spin-casting methods from chloroform and were subjected to impedance spectroscopy. The pristine films showed very low conductivity at open circuit potentials (undoped); however, electrochemically p-doping resulted in stable films with four orders of magnitude higher conductivity.
Thiophene-containing porphyrin compounds are capable of catalytic, photo-reductive dehalogenation on an array of α-halo ketone model substrates with low catalyst loadings (0.1 mol%), in the presence of low energy, red light (>645 nm).
Three donor–acceptor–donor (D–A–D) pyrene chromophores are described and compared by DFT computations. The two properties of low energy photon absorption and low energy electrochemical reduction are demonstrated through a pyrene framework. Altering the electron‐acceptor strength of the pyrene core by chemical oxidation or installation of a thiadiazole dioxide heterocycle results in the formation of D–A–D chromophores with absorption bands up to 900 nm and LUMO energy levels of approximately –4.1 eV vs. vacuum.
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