Air-stable and eco-friendly symmetrical imine with thiadiazole moieties in neutral and protonated form for perovskite photovoltaics

2024
journal article
article
dc.abstract.enThis 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 $^{1}$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.
dc.affiliationWydział Fizyki, Astronomii i Informatyki Stosowanej : Instytut Fizyki im. Mariana Smoluchowskiego
dc.contributor.authorBogdanowicz, Krzysztof Artur
dc.contributor.authorIwan, Agnieszka
dc.contributor.authorDysz, Karolina
dc.contributor.authorPrzybyl, Wojciech
dc.contributor.authorMarzec, Monika - 100126
dc.contributor.authorCichy, Kacper
dc.contributor.authorŚwierczek, Konrad
dc.date.accessioned2024-05-13T08:39:59Z
dc.date.available2024-05-13T08:39:59Z
dc.date.issued2024
dc.date.openaccess0
dc.description.accesstimew momencie opublikowania
dc.description.number8
dc.description.versionostateczna wersja wydawcy
dc.description.volume17
dc.identifier.articleid1909
dc.identifier.doi10.3390/ma17081909
dc.identifier.issn1996-1944
dc.identifier.projectNo. V4-Korea/1/2018
dc.identifier.projectPOIG.02.01.00-12-023/08
dc.identifier.urihttps://ruj.uj.edu.pl/handle/item/339324
dc.languageeng
dc.language.containereng
dc.rightsUdzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa
dc.rights.licenceCC-BY
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/legalcode.pl
dc.share.typeotwarte czasopismo
dc.subject.enimine
dc.subject.enazomethine
dc.subject.ennon-covalent interactions
dc.subject.enhole-transporting material
dc.subject.enthermographic camera
dc.subtypeArticle
dc.titleAir-stable and eco-friendly symmetrical imine with thiadiazole moieties in neutral and protonated form for perovskite photovoltaics
dc.title.journalMaterials
dc.typeJournalArticle
dspace.entity.typePublicationen
dc.abstract.en
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 $^{1}$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.
dc.affiliation
Wydział Fizyki, Astronomii i Informatyki Stosowanej : Instytut Fizyki im. Mariana Smoluchowskiego
dc.contributor.author
Bogdanowicz, Krzysztof Artur
dc.contributor.author
Iwan, Agnieszka
dc.contributor.author
Dysz, Karolina
dc.contributor.author
Przybyl, Wojciech
dc.contributor.author
Marzec, Monika - 100126
dc.contributor.author
Cichy, Kacper
dc.contributor.author
Świerczek, Konrad
dc.date.accessioned
2024-05-13T08:39:59Z
dc.date.available
2024-05-13T08:39:59Z
dc.date.issued
2024
dc.date.openaccess
0
dc.description.accesstime
w momencie opublikowania
dc.description.number
8
dc.description.version
ostateczna wersja wydawcy
dc.description.volume
17
dc.identifier.articleid
1909
dc.identifier.doi
10.3390/ma17081909
dc.identifier.issn
1996-1944
dc.identifier.project
No. V4-Korea/1/2018
dc.identifier.project
POIG.02.01.00-12-023/08
dc.identifier.uri
https://ruj.uj.edu.pl/handle/item/339324
dc.language
eng
dc.language.container
eng
dc.rights
Udzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa
dc.rights.licence
CC-BY
dc.rights.uri
http://creativecommons.org/licenses/by/4.0/legalcode.pl
dc.share.type
otwarte czasopismo
dc.subject.en
imine
dc.subject.en
azomethine
dc.subject.en
non-covalent interactions
dc.subject.en
hole-transporting material
dc.subject.en
thermographic camera
dc.subtype
Article
dc.title
Air-stable and eco-friendly symmetrical imine with thiadiazole moieties in neutral and protonated form for perovskite photovoltaics
dc.title.journal
Materials
dc.type
JournalArticle
dspace.entity.typeen
Publication
Affiliations

* The migration of download and view statistics prior to the date of April 8, 2024 is in progress.

Views
9
Views per month
Views per city
Krakow
4
Downloads
marzec_et-al_air-stable_and_eco-friendly_symmetrical_2024.pdf
1