title: Symmetrical N-acylsubstituted dihydrazones containing bithiophene core--Photophysical, electrochemical and thermal characterization.
abstract: Four symmetrical N-acylsubstituted dihydrazones containing bithiophene core were synthesized from condensation of 2,2'-bithiophene-5,5'-dicarboxyaldehyde with benzoic, isonicotinoyl, 2-thiophenic and 2-furoic hydrazide. The obtained compounds were characterized through the data from (1)H nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), elemental analysis, UV-vis absorption spectroscopy, photoluminescence (PL), cyclic voltammetry (CV) and differential pulse voltammetry (DPV) measurements. Additionally, the electronic properties including orbital energies and resulting energy gaps were calculated by density functional theory (DFT). Their thermal behavior was investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). They were thermal sable up to 320°C. The prepared N-acylsubstituted dihydrazones emitted light with λ(em) in the range of 499-530 nm in solution, whereas, in solid state as blend with PMMA blue emission was observed. They undergo quasi-reversible and irreversible electrochemical reduction and oxidation processes, respectively. Additionally, the selected compounds were tested preliminary as component of active layer in organic photovoltaic cells. The highest value of power conversion efficiency, equal to 1.68% under simulated 100 mW/cm(2) AM 1.5G irradiation was found for device with the architecture ITO/PEDOT:PSS/P3HT:PCBM:FBTH (1:2:2)/Al.
authors: Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
authors: Anna
authors: A
authors: Jarczyk-Jedryka
authors: Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
authors: Michal
authors: M
authors: Filapek
authors: Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
authors: Grzegorz
authors: G
authors: Malecki
authors: Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
authors: Slawomir
authors: S
authors: Kula
authors: Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland.
authors: Henryk
authors: H
authors: Janeczek
authors: Electrotechnical Institute, Division of Electrotechnology and Materials Science, 55/61 M. Sklodowskiej-Curie Str., 50-369 Wroclaw, Poland.
authors: Bartosz
authors: B
authors: Boharewicz
authors: Electrotechnical Institute, Division of Electrotechnology and Materials Science, 55/61 M. Sklodowskiej-Curie Str., 50-369 Wroclaw, Poland.
authors: Agnieszka
authors: A
authors: Iwan
authors: Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland; Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland. Electronic address: ewa.schab-balcerzak@us.edu.pl.
authors: Ewa
authors: E
authors: Schab-Balcerzak
keywords: Acylhydrazones; DFT calculation; Electrochemistry; Photoluminescence