Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester
A new series of thiophene-based azomethines differing in the core structure was synthesized. The effect of the central core structure in azomethines on the thermal, optical and electrochemical properties was investigated. The obtained compounds exhibited the ability to form a stable amorphous phase...
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MDPI AG
2022-07-01
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| Series: | International Journal of Molecular Sciences |
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| author | Agnieszka Katarzyna Pająk Sonia Kotowicz Paweł Gnida Jan Grzegorz Małecki Agnieszka Ciemięga Adam Łuczak Jarosław Jung Ewa Schab-Balcerzak |
| author_facet | Agnieszka Katarzyna Pająk Sonia Kotowicz Paweł Gnida Jan Grzegorz Małecki Agnieszka Ciemięga Adam Łuczak Jarosław Jung Ewa Schab-Balcerzak |
| author_sort | Agnieszka Katarzyna Pająk |
| collection | DOAJ |
| description | A new series of thiophene-based azomethines differing in the core structure was synthesized. The effect of the central core structure in azomethines on the thermal, optical and electrochemical properties was investigated. The obtained compounds exhibited the ability to form a stable amorphous phase with a high glass transition temperature above 100 °C. They were electrochemically active and undergo oxidation and reduction processes. The highest occupied (HOMO) and the lowest unoccupied molecular (LUMO) orbitals were in the range of −3.86–−3.60 eV and −5.46–−5.17 eV, respectively, resulting in a very low energy band gap below 1.7 eV. Optical investigations were performed in the solvents with various polarity and in the solid state as a thin film deposited on a glass substrate. The synthesized imines absorbed radiation from 350 to 600 nm, depending on its structure and showed weak emission with a photoluminescence quantum yield below 2.5%. The photophysical investigations were supported by theoretical calculations using the density functional theory. The synthesized imines doped with lithium bis-(trifluoromethanesulfonyl)imide were examined as hole transporting materials (HTM) in hybrid inorganic-organic perovskite solar cells. It was found that both a volume of lithium salt and core imine structure significantly impact device performance. The best power conversion efficiency (PCE), being about 35–63% higher compared to other devices, exhibited cells based on the imine containing a core tiphenylamine unit. |
| first_indexed | 2024-03-09T12:35:56Z |
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| id | doaj.art-64a78a191d26452caf10f63858f34408 |
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| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T12:35:56Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-64a78a191d26452caf10f63858f344082023-11-30T22:24:13ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-07-012315816010.3390/ijms23158160Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl EsterAgnieszka Katarzyna Pająk0Sonia Kotowicz1Paweł Gnida2Jan Grzegorz Małecki3Agnieszka Ciemięga4Adam Łuczak5Jarosław Jung6Ewa Schab-Balcerzak7Institute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, PolandInstitute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, PolandCentre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze, PolandInstitute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, PolandInstitute of Chemical Engineering, Polish Academy of Sciences, 5 Bałtycka Str., 44-100 Gliwice, PolandDepartment of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, 116 Żeromskiego Str., 90-924 Lodz, PolandDepartment of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, 116 Żeromskiego Str., 90-924 Lodz, PolandInstitute of Chemistry, University of Silesia, 9 Szkolna Str., 40-006 Katowice, PolandA new series of thiophene-based azomethines differing in the core structure was synthesized. The effect of the central core structure in azomethines on the thermal, optical and electrochemical properties was investigated. The obtained compounds exhibited the ability to form a stable amorphous phase with a high glass transition temperature above 100 °C. They were electrochemically active and undergo oxidation and reduction processes. The highest occupied (HOMO) and the lowest unoccupied molecular (LUMO) orbitals were in the range of −3.86–−3.60 eV and −5.46–−5.17 eV, respectively, resulting in a very low energy band gap below 1.7 eV. Optical investigations were performed in the solvents with various polarity and in the solid state as a thin film deposited on a glass substrate. The synthesized imines absorbed radiation from 350 to 600 nm, depending on its structure and showed weak emission with a photoluminescence quantum yield below 2.5%. The photophysical investigations were supported by theoretical calculations using the density functional theory. The synthesized imines doped with lithium bis-(trifluoromethanesulfonyl)imide were examined as hole transporting materials (HTM) in hybrid inorganic-organic perovskite solar cells. It was found that both a volume of lithium salt and core imine structure significantly impact device performance. The best power conversion efficiency (PCE), being about 35–63% higher compared to other devices, exhibited cells based on the imine containing a core tiphenylamine unit.https://www.mdpi.com/1422-0067/23/15/8160thiopheneazomethinesimines3,4-diethyl ester 2,5-diaminothiophenethiophenoazomethines |
| spellingShingle | Agnieszka Katarzyna Pająk Sonia Kotowicz Paweł Gnida Jan Grzegorz Małecki Agnieszka Ciemięga Adam Łuczak Jarosław Jung Ewa Schab-Balcerzak Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester International Journal of Molecular Sciences thiophene azomethines imines 3,4-diethyl ester 2,5-diaminothiophene thiophenoazomethines |
| title | Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester |
| title_full | Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester |
| title_fullStr | Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester |
| title_full_unstemmed | Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester |
| title_short | Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester |
| title_sort | synthesis and characterization of new conjugated azomethines end capped with amino thiophene 3 4 dicarboxylic acid diethyl ester |
| topic | thiophene azomethines imines 3,4-diethyl ester 2,5-diaminothiophene thiophenoazomethines |
| url | https://www.mdpi.com/1422-0067/23/15/8160 |
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