Air-Stable and Eco-Friendly Symmetrical Imine with Thiadiazole Moieties in Neutral and Protonated form for Perovskite Photovoltaics
This paper proposes molecular and supramolecular concepts for potential application in perovskite solar cells. New air-stable symmetrical imine, with thiadiazole moieties PPL2: (5E,6E)-N2,N5-bis(4-(diphenylamino)benzylidene)-1,3,4-thiadiazole-2,5-diamine), as a hole-transporting material was synthes...
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description | This paper proposes molecular and supramolecular concepts for potential application in perovskite solar cells. New air-stable symmetrical imine, with thiadiazole moieties PPL2: (5E,6E)-N2,N5-bis(4-(diphenylamino)benzylidene)-1,3,4-thiadiazole-2,5-diamine), as a hole-transporting material was synthesised in a single-step reaction, starting with commercially available and relatively inexpensive reagents, resulting in a reduction in the cost of the final product compared to Spiro-OMeTAD. Moreover, camphorsulfonic acid (CSA) in both enantiomeric forms was used to change the HOMO-LUMO levels and electric properties of the investigated imine-forming complexes. Electric, optical, thermal, and structural studies of the imine and its complexes with CSA were carried out to characterise the new material. Imine and imine/CSA complexes were also characterised in depth by the proton Nuclear Magnetic Resonance
H NMR method. The position of nitrogen in the thidiazole ring influences the basicity of donor centres, which results in protonation in the imine bond. Simple devices of ITO/imine (with or without CSA(-) or CSA(+))/Ag/ITO architecture were constructed, and a thermographic camera was used to find the defects in the created devices. Electric behaviour was also studied to demonstrate conductivity properties under the forward current. Finally, the electrical properties of imine and its protonated form with CSA were compared with Spiro-OMeTAD. In general, the analysis of thermal images showed a very similar response of the samples to the applied potential in terms of the homogeneity of the formed organic layer. The TGA analysis showed that the investigated imine exhibits good thermal stability in air and argon atmospheres. |
doi_str_mv | 10.3390/ma17081909 |
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H NMR method. The position of nitrogen in the thidiazole ring influences the basicity of donor centres, which results in protonation in the imine bond. Simple devices of ITO/imine (with or without CSA(-) or CSA(+))/Ag/ITO architecture were constructed, and a thermographic camera was used to find the defects in the created devices. Electric behaviour was also studied to demonstrate conductivity properties under the forward current. Finally, the electrical properties of imine and its protonated form with CSA were compared with Spiro-OMeTAD. In general, the analysis of thermal images showed a very similar response of the samples to the applied potential in terms of the homogeneity of the formed organic layer. The TGA analysis showed that the investigated imine exhibits good thermal stability in air and argon atmospheres.</description><identifier>ISSN: 1996-1944</identifier><identifier>EISSN: 1996-1944</identifier><identifier>DOI: 10.3390/ma17081909</identifier><identifier>PMID: 38673266</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Argon ; Basicity ; Cameras ; Chemical reduction ; Chemical synthesis ; Comparative analysis ; Diamines ; Electric properties ; Electrical properties ; Ethanol ; Fourier transforms ; Homogeneity ; Molecular orbitals ; NMR ; Nuclear magnetic resonance ; Optical properties ; Perovskite ; Perovskites ; Photovoltaic cells ; Protonation ; Reagents ; Solar cells ; Solar energy industry ; Thermal imaging ; Thermal stability ; Thermography ; Thiadiazoles ; Voltammetry</subject><ispartof>Materials, 2024-04, Vol.17 (8), p.1909</ispartof><rights>COPYRIGHT 2024 MDPI AG</rights><rights>2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c349t-10ed5bc756f942c6ffada981c0b84dcde2e73f4f9a8f5ded480ff793a78e3ca43</cites><orcidid>0000-0001-8526-626X ; 0000-0003-4519-389X ; 0000-0002-0384-3463 ; 0000-0002-6784-6401 ; 0000-0002-4854-9567</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38673266$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bogdanowicz, Krzysztof Artur</creatorcontrib><creatorcontrib>Iwan, Agnieszka</creatorcontrib><creatorcontrib>Dysz, Karolina</creatorcontrib><creatorcontrib>Przybyl, Wojciech</creatorcontrib><creatorcontrib>Marzec, Monika</creatorcontrib><creatorcontrib>Cichy, Kacper</creatorcontrib><creatorcontrib>Świerczek, Konrad</creatorcontrib><title>Air-Stable and Eco-Friendly Symmetrical Imine with Thiadiazole Moieties in Neutral and Protonated form for Perovskite Photovoltaics</title><title>Materials</title><addtitle>Materials (Basel)</addtitle><description>This paper proposes molecular and supramolecular concepts for potential application in perovskite solar cells. New air-stable symmetrical imine, with thiadiazole moieties PPL2: (5E,6E)-N2,N5-bis(4-(diphenylamino)benzylidene)-1,3,4-thiadiazole-2,5-diamine), as a hole-transporting material was synthesised in a single-step reaction, starting with commercially available and relatively inexpensive reagents, resulting in a reduction in the cost of the final product compared to Spiro-OMeTAD. Moreover, camphorsulfonic acid (CSA) in both enantiomeric forms was used to change the HOMO-LUMO levels and electric properties of the investigated imine-forming complexes. Electric, optical, thermal, and structural studies of the imine and its complexes with CSA were carried out to characterise the new material. Imine and imine/CSA complexes were also characterised in depth by the proton Nuclear Magnetic Resonance
H NMR method. The position of nitrogen in the thidiazole ring influences the basicity of donor centres, which results in protonation in the imine bond. Simple devices of ITO/imine (with or without CSA(-) or CSA(+))/Ag/ITO architecture were constructed, and a thermographic camera was used to find the defects in the created devices. Electric behaviour was also studied to demonstrate conductivity properties under the forward current. Finally, the electrical properties of imine and its protonated form with CSA were compared with Spiro-OMeTAD. In general, the analysis of thermal images showed a very similar response of the samples to the applied potential in terms of the homogeneity of the formed organic layer. The TGA analysis showed that the investigated imine exhibits good thermal stability in air and argon atmospheres.</description><subject>Argon</subject><subject>Basicity</subject><subject>Cameras</subject><subject>Chemical reduction</subject><subject>Chemical synthesis</subject><subject>Comparative analysis</subject><subject>Diamines</subject><subject>Electric properties</subject><subject>Electrical properties</subject><subject>Ethanol</subject><subject>Fourier transforms</subject><subject>Homogeneity</subject><subject>Molecular orbitals</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Optical properties</subject><subject>Perovskite</subject><subject>Perovskites</subject><subject>Photovoltaic cells</subject><subject>Protonation</subject><subject>Reagents</subject><subject>Solar cells</subject><subject>Solar energy industry</subject><subject>Thermal imaging</subject><subject>Thermal stability</subject><subject>Thermography</subject><subject>Thiadiazoles</subject><subject>Voltammetry</subject><issn>1996-1944</issn><issn>1996-1944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNpdkV9vFCEUxYnR2Kb2xQ9gSHwxJlNhYQZ43DStNqm6SevzhIWLSx2gAlOzvvrFy3brn8hNgMDv3Jybg9BLSk4YU-Rd0FQQSRVRT9AhVWroqOL86T_3A3Rcyg1pizEqF-o5OmByEGwxDIfo19Ln7qrq9QRYR4vPTOrOs4dopy2-2oYANXujJ3wRfAT8w9cNvt54bb3-mZrmY_JQPRTsI_4Ec80N3fVZ5VRT1BUsdimH3YZXkNNd-eYr4NWmfd-lqWpvygv0zOmpwPHjeYS-nJ9dn37oLj-_vzhdXnaGcVU7SsD2ayP6wSm-MINz2molqSFrya2xsADBHHdKS9dbsFwS54RiWkhgRnN2hN7s-97m9H2GUsfgi4Fp0hHSXEZGuFA9kYI29PV_6E2ac2zuHihCetKLRp3sqa96gtFHl9r8ppWF4E2K4Hx7XzYPfS-HYSd4uxeYnErJ4Mbb7IPO25GScRfn-DfOBr969DCvA9g_6O_w2D0yK5v6</recordid><startdate>20240420</startdate><enddate>20240420</enddate><creator>Bogdanowicz, Krzysztof Artur</creator><creator>Iwan, Agnieszka</creator><creator>Dysz, Karolina</creator><creator>Przybyl, Wojciech</creator><creator>Marzec, Monika</creator><creator>Cichy, Kacper</creator><creator>Świerczek, Konrad</creator><general>MDPI AG</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8526-626X</orcidid><orcidid>https://orcid.org/0000-0003-4519-389X</orcidid><orcidid>https://orcid.org/0000-0002-0384-3463</orcidid><orcidid>https://orcid.org/0000-0002-6784-6401</orcidid><orcidid>https://orcid.org/0000-0002-4854-9567</orcidid></search><sort><creationdate>20240420</creationdate><title>Air-Stable and Eco-Friendly Symmetrical Imine with Thiadiazole Moieties in Neutral and Protonated form for Perovskite Photovoltaics</title><author>Bogdanowicz, Krzysztof Artur ; 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New air-stable symmetrical imine, with thiadiazole moieties PPL2: (5E,6E)-N2,N5-bis(4-(diphenylamino)benzylidene)-1,3,4-thiadiazole-2,5-diamine), as a hole-transporting material was synthesised in a single-step reaction, starting with commercially available and relatively inexpensive reagents, resulting in a reduction in the cost of the final product compared to Spiro-OMeTAD. Moreover, camphorsulfonic acid (CSA) in both enantiomeric forms was used to change the HOMO-LUMO levels and electric properties of the investigated imine-forming complexes. Electric, optical, thermal, and structural studies of the imine and its complexes with CSA were carried out to characterise the new material. Imine and imine/CSA complexes were also characterised in depth by the proton Nuclear Magnetic Resonance
H NMR method. The position of nitrogen in the thidiazole ring influences the basicity of donor centres, which results in protonation in the imine bond. Simple devices of ITO/imine (with or without CSA(-) or CSA(+))/Ag/ITO architecture were constructed, and a thermographic camera was used to find the defects in the created devices. Electric behaviour was also studied to demonstrate conductivity properties under the forward current. Finally, the electrical properties of imine and its protonated form with CSA were compared with Spiro-OMeTAD. In general, the analysis of thermal images showed a very similar response of the samples to the applied potential in terms of the homogeneity of the formed organic layer. The TGA analysis showed that the investigated imine exhibits good thermal stability in air and argon atmospheres.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>38673266</pmid><doi>10.3390/ma17081909</doi><orcidid>https://orcid.org/0000-0001-8526-626X</orcidid><orcidid>https://orcid.org/0000-0003-4519-389X</orcidid><orcidid>https://orcid.org/0000-0002-0384-3463</orcidid><orcidid>https://orcid.org/0000-0002-6784-6401</orcidid><orcidid>https://orcid.org/0000-0002-4854-9567</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Argon Basicity Cameras Chemical reduction Chemical synthesis Comparative analysis Diamines Electric properties Electrical properties Ethanol Fourier transforms Homogeneity Molecular orbitals NMR Nuclear magnetic resonance Optical properties Perovskite Perovskites Photovoltaic cells Protonation Reagents Solar cells Solar energy industry Thermal imaging Thermal stability Thermography Thiadiazoles Voltammetry |
title | Air-Stable and Eco-Friendly Symmetrical Imine with Thiadiazole Moieties in Neutral and Protonated form for Perovskite Photovoltaics |
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