Symmetrical N-acylsubstituted dihydrazones containing bithiophene core--Photophysical, electrochemical and thermal characterization

Anna Jarczyk-Jedryka; Michal Filapek; Grzegorz Malecki; Slawomir Kula; Henryk Janeczek; Bartosz Boharewicz; Agnieszka Iwan; Ewa Schab-Balcerzak

doi:10.1016/j.saa.2016.01.034

Symmetrical N-acylsubstituted dihydrazones containing bithiophene core--Photophysical, electrochemical and thermal characterization

Spectrochim Acta A Mol Biomol Spectrosc. 2016 Apr 15:159:169-76. doi: 10.1016/j.saa.2016.01.034. Epub 2016 Jan 25.

Authors

Anna Jarczyk-Jedryka¹, Michal Filapek¹, Grzegorz Malecki¹, Slawomir Kula¹, Henryk Janeczek², Bartosz Boharewicz³, Agnieszka Iwan³, Ewa Schab-Balcerzak⁴

Affiliations

¹ Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, Poland.
² Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, Poland.
³ Electrotechnical Institute, Division of Electrotechnology and Materials Science, 55/61 M. Sklodowskiej-Curie Str., 50-369 Wroclaw, Poland.
⁴ 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.

PMID: 26845584
DOI: 10.1016/j.saa.2016.01.034

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.

Keywords: Acylhydrazones; DFT calculation; Electrochemistry; Photoluminescence.

Publication types

Research Support, Non-U.S. Gov't