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An arylene-vinylene based donor-acceptor-donor small molecule for the donor compound in high-voltage organic solar cells
Umeå University, Faculty of Science and Technology, Department of Chemistry. Department of Chemistry, University of Agriculture, Faisalabad 38040, Pakistan.
Umeå University, Faculty of Science and Technology, Department of Physics.
Umeå University, Faculty of Science and Technology, Department of Physics.
Umeå University, Faculty of Science and Technology, Department of Physics.
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2016 (English)In: Solar Energy Materials and Solar Cells, ISSN 0927-0248, E-ISSN 1879-3398, Vol. 155, p. 348-355Article in journal (Refereed) Published
Abstract [en]

A donor-acceptor-donor (D-A-D) molecule has been designed and synthesized for use as the electron donating material in solution-processed small-molecule organic solar cells (OSCs). The D-A-D molecule comprises a central electron-accepting (2Z,2'Z)-2,2'-(2,5-bis(octyloxy)-1,4-phenylene)bis(3-(thiophen-2-yl)acry lonitrile) (ZOPTAN) core, which is chemically connected to two peripheral and electron-donating triphenylamine (TPA) units. The ZOPTAN-TPA molecule features a low HOMO level of -5.2 eV and an optical energy gap of 2.1 eV. Champion OSCs based on a solution-processed and non-annealed active material blend of [6,6]-phenyl-C-61-butyric acid methyl ester (PCBM) and ZOPTAN-TPA in a mass ratio of 2:1 exhibits a power conversion efficiency of 1.9% and a high open-circuit voltage of 1.0 V. 

Place, publisher, year, edition, pages
2016. Vol. 155, p. 348-355
Keywords [en]
Organic solar cell, Small-molecule donor, Fullerene acceptor, Solution processing, High open-circuit ltage, Thermal stability
National Category
Atom and Molecular Physics and Optics
Identifiers
URN: urn:nbn:se:umu:diva-126290DOI: 10.1016/j.solmat.2016.06.018ISI: 000381529100040OAI: oai:DiVA.org:umu-126290DiVA, id: diva2:1045122
Available from: 2016-11-08 Created: 2016-10-03 Last updated: 2018-06-09Bibliographically approved
In thesis
1. Molecular design, synthesis and performance evaluation of phenothiazine-based small molecules for efficient organic solar cells
Open this publication in new window or tab >>Molecular design, synthesis and performance evaluation of phenothiazine-based small molecules for efficient organic solar cells
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Alternative title[sv]
Design, syntes och utvärdering av fenotiazin-innehållande små molekyler till effektiva organiska solceller
Abstract [en]

Photovoltaics offers one of the most promising routes to generate electricity in a clean way. As an emerging technology in photovoltaics, organic solar cells (OSC) have attracted a great deal of attention owing to their potential low-cost, lightweight, flexibility and solution processability. Although power conversion efficiencies above 12% have been achieved at this date, there is a great interest for new ideal materials to further improve the PCEs and address device durability, which are major concerns for the commercialization of this technology. The main objective of this thesis is to design and synthesize phenothiazine-based conjugate small molecules and explore their use as electron donor components in OSCs. Phenothiazine is a non-planar moiety with unusual “butterfly” type of geometry, which is known to reduce molecular aggregation and intermolecular excimer formation.

In the first study of this thesis, a small molecule based on a cyano-arylenevinylene building block with deep HOMO level was prepared. Although a high open-circuit voltage of 1.0 V was achieved, the tendency of the small molecule to crystallize in the active layer at a higher temperature and with time hindered the attainment of an optimal phase morphology required for the achievement of a higher efficiency. In the second and third studies, phenothiazine was used as a π-system bridge and as a core unit to construct small molecules based on symmetric and asymmetric frameworks with varying terminal electron-withdrawing groups. The electron-withdrawing property of the terminal units was found to have a significant influence on the optical absorption properties, electronic energy levels, molecular ordering, charge carrier mobility and morphology of the resulting active layers. In the fourth study, side-chain modification of the phenothiazine unit of symmetrically configured small molecules with an oxygen-containing (methoxyethoxy ethyl) side chain resulted in the enhancement of the dielectric constant. Although absorption properties were unchanged in solution, a dense π-π stacking was observed in the solid state.

In summary, it is demonstrated that phenothiazine is a promising candidate and worth exploring donor material for OSCs. Its versatility as a π-linker and as a central core unit in symmetric and asymmetric configurations has been explored. The use of nonplanar building blocks such as phenothiazine for the construction of donor materials is an interesting strategy for controlling molecular aggregation and difficult solution processability of small molecules if it is combined with a judiciously designed conjugate backbone.

Place, publisher, year, edition, pages
Umeå: Umeå University, 2018. p. 90
Keywords
Organic solar cell, small molecule donors, phenothiazine, power conversion efficiency
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-144465 (URN)978-91-7601-835-4 (ISBN)
Public defence
2018-02-28, KBE301 - Lilla Hörsalen, KBC-huset, Umeå, 10:00 (English)
Opponent
Supervisors
Available from: 2018-02-07 Created: 2018-02-04 Last updated: 2018-06-09Bibliographically approved

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Iqbal, JavedEnevold, JennyLarsen, ChristianWang, JiaRevoju, SrikanthBarzegar, Hamid RezaWågberg, ThomasEliasson, BertilEdman, Ludvig

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Iqbal, JavedEnevold, JennyLarsen, ChristianWang, JiaRevoju, SrikanthBarzegar, Hamid RezaWågberg, ThomasEliasson, BertilEdman, Ludvig
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Department of ChemistryDepartment of Physics
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Atom and Molecular Physics and Optics

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