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Electrochemical Characterization of Various Diketopyrrolopyrrole Derivatives with Respect to HOMO/LUMO Energies

Autoři: Mikysek Tomáš | Ludvík Jiří

Rok: 2015

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

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Jazyk	Název	Abstrakt	Klíčová slova
eng	Electrochemical Characterization of Various Diketopyrrolopyrrole Derivatives with Respect to HOMO/LUMO Energies	Recently, solar cells (SC) based on bulk heterojunction (BHJ) architecture belong to one of the most promising organic photovoltaic (OPV) technologies [1]. While fullerene derivatives are successfully used as electron acceptors in these cells, a progress has been made in searching new and more efficient donors. One of the examined electron donors are compounds based on 3,6-diphenyl-2,5-dihydro-pyrrolo-[3,4-c]-pyrrole-1,4-dione (DPP) structure. Recently, some new derivatives were synthesized and tested for above mentioned application. In this contribution, some derivatives of DPP were electrochemically investigated and chraracterized using cyclic voltammetry (CV) and rotating disc voltammetry (RDV) at platinum electrode in non-aqueous media (acetonitrile/DMF) in order to estimate the respective reduction and oxidation potentials, to prove the reversibility of these electron transfers and stability of the radical intermediates, to determine electrochemically the HOMO-LUMO gap, to describe the influence of various substituents and to localize the first oxidation and first reduction center (that means the HOMO and LUMO orbitals) on the molecule. From the CV and RDV experiments resulted that there are two reversible redox processes. In the structure, where two piperidine heterocycles bind to both phenyl goups it has been found that the first oxidation process consumed two electrons (concerted) whereas the derivative with only one piperidine group showed only one-electron oxidation process as well as reduction processes in both derivatives. The oxidation has been also performed by chemical way (with FeCl3) and the result was rather surprising when the oxidation showed to be stepwise [2]. The further experimental data interpretation was focused on influence of N-alkyl or N-ester substitution in pyrrole structure on first oxidation (HOMO) and first reduction (LUMO) processes. Both of the substitutions establish solubility of DPP derivatives in organic solvents.	HOMO; LUMO; cyclic voltammetry; non-aqueous media; oxidation and reduction potentials

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