Electrochemical, photovoltaic and DFT studies on hybrid materials based on supramolecular self-assembly of a ditopic twisted perylene diimide with square-planar platinum(II)- and/or palladium(II)-2,2':6',2¨-terpyridyl complex ions

A ditopic bridging ligand, N,N'-bis(pyridine)-1,6,7,12-tetrakis-(4-methoxyphenoxy)perylene diimide (1) was synthesized. Metallosupramolecular self-assembly of 1 with 2,2':6',2¨-terpyridyl-platinum(II) and/or -palladium(II) complex ions afforded to new triads [(terpy)M(II)-(1)-M(II)(terpy)](NO3)4 where, M(II) = Pt(II) (2), and Pd(II) (3), respectively. These isolated triads 2 and 3 and also free ligand 1 were fully characterized by FT-IR, 1H NMR, 13C DEPT NMR, 1H-1H COSY NMR, MALDI TOF and HRMS (MALDI-TOF/TOF-MS) mass techniques and UV/Vis spectroscopy. DFT studies revealed that the molecular structure of 1 is highly distorted and deviated from the planarity by bulky methoxyphenyl groups at bay positions. The calculated HOMO and LUMO are located on the PDI core and phenyl groups, and the band gap was found to be 2.27, 2.23 and 2.24 eV in DMSO for 1, 2 and 3, respectively. The calculated UV/Vis spectra are in good agreement with those of experimental results. Electrochemical, in situ spectroelectrochemical and in situ electrocolorimetric measurements in solution suggested that redox processes of the compounds are accompanied by favourable electron transport properties with remarkably narrow HOMO-LUMO gaps and intense light absorption over the visible range. The association of usually reversible and fast electron transfer processes with the net colour changes in solution pointed out the applicability of the compounds as an electrochromic material. The electrochromic performance measurements with the films of the compounds on indium tin oxide glass provided additional support for their usability as a colour changing material in electrochromic devices. Surface morphologies of the films were characterized by scanning electron microscopy (SEM). The metal complexes of 1, especially the platinum(II) complex (2), behaved as a good neutral and cathodic colouring electrochromic material with fast response time, long-term stability, and long-term write erase efficiency. The photovoltaic performance of the compounds as electron acceptor material was investigated by varying their relative ratio in the bulk heterojunction solar cells. It was found that the photovoltaic conversion efficiency of the devices strongly depends on the blend ratio. The optimized performance for the devices was obtained with the P3HT:PDIs (weight ratio 1.0:1.5) blended films. For this blend ratio, the device showed a maximum conversion efficiency of 3.91%, 8.17% and 5.18% for 1, 2 and 3, respectively. The results obtained reveal that employing 2 as an acceptor material has great potential for the development of highly efficient nonfullerene bulk heterojunction photovoltaic devices. © 2018

Yazar Işık Büyükekşi S.
Orman E.B.
Acar N.
Altındal A.
Özkaya A.R.
Şengül A.
Yayın Türü Article
Tek Biçim Adres https://hdl.handle.net/20.500.12628/5589
Tek Biçim Adres 10.1016/j.dyepig.2018.09.022
Konu Başlıkları Density functional theory
Perylene diimide (PDI)
Photovoltaics
Pyridine
Square-planar complexes
Terpyridine
Koleksiyonlar Araştırma Çıktıları | WoS | Scopus | TR-Dizin | PubMed | SOBİAD
Scopus İndeksli Yayınlar Koleksiyonu
Dergi Adı Dyes and Pigments
Dergi Cilt Bilgisi 161
Sayfalar 66 - 78
Yayın Yılı 2019
Eser Adı
[dc.title]
Electrochemical, photovoltaic and DFT studies on hybrid materials based on supramolecular self-assembly of a ditopic twisted perylene diimide with square-planar platinum(II)- and/or palladium(II)-2,2':6',2¨-terpyridyl complex ions
Yazar
[dc.contributor.author]
Işık Büyükekşi S.
Yazar
[dc.contributor.author]
Orman E.B.
Yazar
[dc.contributor.author]
Acar N.
Yazar
[dc.contributor.author]
Altındal A.
Yazar
[dc.contributor.author]
Özkaya A.R.
Yazar
[dc.contributor.author]
Şengül A.
Yayın Yılı
[dc.date.issued]
2019
Yayıncı
[dc.publisher]
Elsevier Ltd
Yayın Türü
[dc.type]
article
Özet
[dc.description.abstract]
A ditopic bridging ligand, N,N'-bis(pyridine)-1,6,7,12-tetrakis-(4-methoxyphenoxy)perylene diimide (1) was synthesized. Metallosupramolecular self-assembly of 1 with 2,2':6',2¨-terpyridyl-platinum(II) and/or -palladium(II) complex ions afforded to new triads [(terpy)M(II)-(1)-M(II)(terpy)](NO3)4 where, M(II) = Pt(II) (2), and Pd(II) (3), respectively. These isolated triads 2 and 3 and also free ligand 1 were fully characterized by FT-IR, 1H NMR, 13C DEPT NMR, 1H-1H COSY NMR, MALDI TOF and HRMS (MALDI-TOF/TOF-MS) mass techniques and UV/Vis spectroscopy. DFT studies revealed that the molecular structure of 1 is highly distorted and deviated from the planarity by bulky methoxyphenyl groups at bay positions. The calculated HOMO and LUMO are located on the PDI core and phenyl groups, and the band gap was found to be 2.27, 2.23 and 2.24 eV in DMSO for 1, 2 and 3, respectively. The calculated UV/Vis spectra are in good agreement with those of experimental results. Electrochemical, in situ spectroelectrochemical and in situ electrocolorimetric measurements in solution suggested that redox processes of the compounds are accompanied by favourable electron transport properties with remarkably narrow HOMO-LUMO gaps and intense light absorption over the visible range. The association of usually reversible and fast electron transfer processes with the net colour changes in solution pointed out the applicability of the compounds as an electrochromic material. The electrochromic performance measurements with the films of the compounds on indium tin oxide glass provided additional support for their usability as a colour changing material in electrochromic devices. Surface morphologies of the films were characterized by scanning electron microscopy (SEM). The metal complexes of 1, especially the platinum(II) complex (2), behaved as a good neutral and cathodic colouring electrochromic material with fast response time, long-term stability, and long-term write erase efficiency. The photovoltaic performance of the compounds as electron acceptor material was investigated by varying their relative ratio in the bulk heterojunction solar cells. It was found that the photovoltaic conversion efficiency of the devices strongly depends on the blend ratio. The optimized performance for the devices was obtained with the P3HT:PDIs (weight ratio 1.0:1.5) blended films. For this blend ratio, the device showed a maximum conversion efficiency of 3.91%, 8.17% and 5.18% for 1, 2 and 3, respectively. The results obtained reveal that employing 2 as an acceptor material has great potential for the development of highly efficient nonfullerene bulk heterojunction photovoltaic devices. © 2018
Kayıt Giriş Tarihi
[dc.date.accessioned]
2019-12-23
Açık Erişim Tarihi
[dc.date.available]
2019-12-23
Yayın Dili
[dc.language.iso]
eng
Konu Başlıkları
[dc.subject]
Density functional theory
Konu Başlıkları
[dc.subject]
Perylene diimide (PDI)
Konu Başlıkları
[dc.subject]
Photovoltaics
Konu Başlıkları
[dc.subject]
Pyridine
Konu Başlıkları
[dc.subject]
Square-planar complexes
Konu Başlıkları
[dc.subject]
Terpyridine
Haklar
[dc.rights]
info:eu-repo/semantics/closedAccess
ISSN
[dc.identifier.issn]
0143-7208
Sponsor YAYINCI
[dc.description.sponsorship]
214Z090
Sponsor YAYINCI
[dc.description.sponsorship]
The authors are grateful to the Turkish Scientific and Technical Research Council for support of this project under the grant [TÜBİTAK-Project No: 214Z090 ]. We also thank for computer time on FenCluster provided by Ege University Faculty of Science and TUBITAK-ULAKBIM Truba Resources. Ali Rıza Özkaya also thanks Turkish Academy of Sciences for partial support to this work. The authors gratefully thank Prof. Dr Bekir SALIH at the Hacettepe University for the MALDI-TOF and HRMS analysis. Appendix A
İlk Sayfa Sayısı
[dc.identifier.startpage]
66
Son Sayfa Sayısı
[dc.identifier.endpage]
78
Dergi Adı
[dc.relation.journal]
Dyes and Pigments
Dergi Cilt Bilgisi
[dc.identifier.volume]
161
Tek Biçim Adres
[dc.identifier.uri]
https://dx.doi.org/10.1016/j.dyepig.2018.09.022
Tek Biçim Adres
[dc.identifier.uri]
https://hdl.handle.net/20.500.12628/5589
Görüntülenme Sayısı ( Şehir )
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Görüntülenme Sayısı ( Zaman Dağılımı )
Görüntülenme
24
09.12.2022 tarihinden bu yana
İndirme
1
09.12.2022 tarihinden bu yana
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08 Nisan 2024 05:41
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material devices compounds electron electrochromic efficiency performance photovoltaic respectively UV/Vis colour heterojunction acceptor groups highly processes long-term calculated solution results conversion measurements characterized triads ligand obtained complex depends additional provided support usability indium potential reveal
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