Spectroscopic and Physicochemical Investigations of Azomethines with Triphenylamine Core towards Optoelectronics

Muhammad Faisal Amin; Paweł Gnida; Sonia Kotowicz; Jan Grzegorz Małecki; Mariola Siwy; Paweł Nitschke; Ewa Schab-Balcerzak

doi:10.3390/ma15207197

Spectroscopic and Physicochemical Investigations of Azomethines with Triphenylamine Core towards Optoelectronics

Materials (Basel). 2022 Oct 15;15(20):7197. doi: 10.3390/ma15207197.

Authors

Muhammad Faisal Amin¹, Paweł Gnida¹, Sonia Kotowicz², Jan Grzegorz Małecki², Mariola Siwy¹, Paweł Nitschke¹, Ewa Schab-Balcerzak^{1

2}

Affiliations

¹ Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Skłodowska Str., 41-819 Zabrze, Poland.
² Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-007 Katowice, Poland.

Abstract

Three new azomethines based on triphenylamine with two or three substituents were obtained. Chemical structure and purity were confirmed by ¹H NMR, FTIR elemental analysis and mass spectroscopy. The investigations were focused on the relationship between chemical structure and properties important for optoelectronic materials. Thus, the studies of thermal, optical and electrochemical properties were carried out based on differential scanning calorimetry, thermogravimetric analysis, electronic absorption, photoluminescence and cyclic voltammetry measurements. The ongoing consideration of experimental results was complemented by theoretical calculations using the density functional theory method. The donor activity of obtained compounds was tested in bulk-heterojuntion photovoltaic cells with structure ITO/PEDOT:PSS/imine:PCBM/Al and ITO/PEDOT:PSS/imine:P3HT:PCBM/Al). The effect of the presence of the amino-thiophene-3,4-dicarboxylic acid diethyl ester groups and various number of hexyloxyphenyl units on imines properties was demonstrated.

Keywords: azomethines; bulk-heterojunction solar cells; photovoltaics; triphenylamine.

Grants and funding

The GAUSSIAN-09 calculations were carried out in the Wrocław Centre for Networking and Supercomputing, WCSS, Wrocław, Poland, http://www.wcss.wroc.pl (accessed date 2 September 2021) (grant No. 18).