Theoretical Study of a Class of Organic D‐π‐A Dyes for Polymer Solar Cells: Influence of Various π‐Spacers
A class of D-π-A compounds that can be used as dyes for applications in polymer solar cells has theoretically been designed and studied, on the basis of the dyes recently shown by experiment to have the highest power conversion efficiency (PCE), namely the poly[4,8-bis(5-(2-butylhexylthio)thiophen-2...
Main Authors: | , , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2020-03-01
|
Series: | Crystals |
Subjects: | |
Online Access: | https://www.mdpi.com/2073-4352/10/3/163 |
id |
doaj-4da9d561ede2400a892bd820721930c7 |
---|---|
record_format |
Article |
spelling |
doaj-4da9d561ede2400a892bd820721930c72020-11-25T00:42:32ZengMDPI AGCrystals2073-43522020-03-0110316310.3390/cryst10030163cryst10030163Theoretical Study of a Class of Organic D‐π‐A Dyes for Polymer Solar Cells: Influence of Various π‐SpacersNguyen Van Trang0Tran Ngoc Dung1Ngo Tuan Cuong2Le Thi Hong Hai3Daniel Escudero4Minh Tho Nguyen5Hue Minh Thi Nguyen6Institute for Tropical Technology, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Hanoi 100000, VietnamDepartment of Chemistry and Center for Computational Science, Hanoi National University of Education, 136 Xuan Thuy, Hanoi 100000, VietnamDepartment of Chemistry and Center for Computational Science, Hanoi National University of Education, 136 Xuan Thuy, Hanoi 100000, VietnamDepartment of Chemistry and Center for Computational Science, Hanoi National University of Education, 136 Xuan Thuy, Hanoi 100000, VietnamDepartment of Chemistry, KU Leuven, B-3001 Leuven, BelgiumDepartment of Chemistry, KU Leuven, B-3001 Leuven, BelgiumDepartment of Chemistry and Center for Computational Science, Hanoi National University of Education, 136 Xuan Thuy, Hanoi 100000, VietnamA class of D-π-A compounds that can be used as dyes for applications in polymer solar cells has theoretically been designed and studied, on the basis of the dyes recently shown by experiment to have the highest power conversion efficiency (PCE), namely the poly[4,8-bis(5-(2-butylhexylthio)thiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene-2,6-diyl-alt-TZNT] (PBDTS-TZNT) and poly[4,8-bis(4-fluoro-5-(2-butylhexylthio)thiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene-2,6-diyl-alt-TZNT] (PBDTSF-TZNT) substances. Electronic structure theory computations were carried out with density functional theory and time-dependent density functional theory methods in conjunction with the 6−311G (d, p) basis set. The PBDTS donor and the TZNT (naphtho[1,2-c:5,6-c]bis(2-octyl-[1,2,3]triazole) acceptor components were established from the original substances upon replacement of long alkyl groups within the thiophene and azole rings with methyl groups. In particular, the effects of several π-spacers were investigated. The calculated results confirmed that dithieno[3,2-b:2′,3′-d] silole (DTS) acts as an excellent π-linker, even better than the thiophene bridge in the original substances in terms of well-known criteria. Indeed, a PBDTS-DTS-TZNT combination forms a D-π-A substance that has a flatter structure, more rigidity in going from the neutral to the cationic form, and a better conjugation than the original compounds. The highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gap of such a D-π-A substance becomes smaller and its absorption spectrum is more intense and red-shifted, which enhances the intramolecular charge transfer and makes it a promising candidate to attain higher PCEs.https://www.mdpi.com/2073-4352/10/3/163d-π-a dyespbdts-tznt and pbdtsf-tzntdtspolymer solar cellspcesdft calculations |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Nguyen Van Trang Tran Ngoc Dung Ngo Tuan Cuong Le Thi Hong Hai Daniel Escudero Minh Tho Nguyen Hue Minh Thi Nguyen |
spellingShingle |
Nguyen Van Trang Tran Ngoc Dung Ngo Tuan Cuong Le Thi Hong Hai Daniel Escudero Minh Tho Nguyen Hue Minh Thi Nguyen Theoretical Study of a Class of Organic D‐π‐A Dyes for Polymer Solar Cells: Influence of Various π‐Spacers Crystals d-π-a dyes pbdts-tznt and pbdtsf-tznt dts polymer solar cells pces dft calculations |
author_facet |
Nguyen Van Trang Tran Ngoc Dung Ngo Tuan Cuong Le Thi Hong Hai Daniel Escudero Minh Tho Nguyen Hue Minh Thi Nguyen |
author_sort |
Nguyen Van Trang |
title |
Theoretical Study of a Class of Organic D‐π‐A Dyes for Polymer Solar Cells: Influence of Various π‐Spacers |
title_short |
Theoretical Study of a Class of Organic D‐π‐A Dyes for Polymer Solar Cells: Influence of Various π‐Spacers |
title_full |
Theoretical Study of a Class of Organic D‐π‐A Dyes for Polymer Solar Cells: Influence of Various π‐Spacers |
title_fullStr |
Theoretical Study of a Class of Organic D‐π‐A Dyes for Polymer Solar Cells: Influence of Various π‐Spacers |
title_full_unstemmed |
Theoretical Study of a Class of Organic D‐π‐A Dyes for Polymer Solar Cells: Influence of Various π‐Spacers |
title_sort |
theoretical study of a class of organic d‐π‐a dyes for polymer solar cells: influence of various π‐spacers |
publisher |
MDPI AG |
series |
Crystals |
issn |
2073-4352 |
publishDate |
2020-03-01 |
description |
A class of D-π-A compounds that can be used as dyes for applications in polymer solar cells has theoretically been designed and studied, on the basis of the dyes recently shown by experiment to have the highest power conversion efficiency (PCE), namely the poly[4,8-bis(5-(2-butylhexylthio)thiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene-2,6-diyl-alt-TZNT] (PBDTS-TZNT) and poly[4,8-bis(4-fluoro-5-(2-butylhexylthio)thiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene-2,6-diyl-alt-TZNT] (PBDTSF-TZNT) substances. Electronic structure theory computations were carried out with density functional theory and time-dependent density functional theory methods in conjunction with the 6−311G (d, p) basis set. The PBDTS donor and the TZNT (naphtho[1,2-c:5,6-c]bis(2-octyl-[1,2,3]triazole) acceptor components were established from the original substances upon replacement of long alkyl groups within the thiophene and azole rings with methyl groups. In particular, the effects of several π-spacers were investigated. The calculated results confirmed that dithieno[3,2-b:2′,3′-d] silole (DTS) acts as an excellent π-linker, even better than the thiophene bridge in the original substances in terms of well-known criteria. Indeed, a PBDTS-DTS-TZNT combination forms a D-π-A substance that has a flatter structure, more rigidity in going from the neutral to the cationic form, and a better conjugation than the original compounds. The highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gap of such a D-π-A substance becomes smaller and its absorption spectrum is more intense and red-shifted, which enhances the intramolecular charge transfer and makes it a promising candidate to attain higher PCEs. |
topic |
d-π-a dyes pbdts-tznt and pbdtsf-tznt dts polymer solar cells pces dft calculations |
url |
https://www.mdpi.com/2073-4352/10/3/163 |
work_keys_str_mv |
AT nguyenvantrang theoreticalstudyofaclassoforganicdpadyesforpolymersolarcellsinfluenceofvariouspspacers AT tranngocdung theoreticalstudyofaclassoforganicdpadyesforpolymersolarcellsinfluenceofvariouspspacers AT ngotuancuong theoreticalstudyofaclassoforganicdpadyesforpolymersolarcellsinfluenceofvariouspspacers AT lethihonghai theoreticalstudyofaclassoforganicdpadyesforpolymersolarcellsinfluenceofvariouspspacers AT danielescudero theoreticalstudyofaclassoforganicdpadyesforpolymersolarcellsinfluenceofvariouspspacers AT minhthonguyen theoreticalstudyofaclassoforganicdpadyesforpolymersolarcellsinfluenceofvariouspspacers AT hueminhthinguyen theoreticalstudyofaclassoforganicdpadyesforpolymersolarcellsinfluenceofvariouspspacers |
_version_ |
1725281828986683392 |