Electron-Accepting π-Conjugated Compound Containing Cyano-Substituted Naphthobisthiadiazole for Nonfullerene Acceptor in Organic Solar Cells

Synthesis ◽  
2021 ◽  
Author(s):  
Seihou Jinnai ◽  
Ayumi Oi ◽  
Takuji Seo ◽  
Taichi Moriyama ◽  
Ryunosuke Minami ◽  
...  
Keyword(s):  
Solar Cells ◽  
Organic Solar Cells ◽  
Energy Levels ◽  
Orbital Energy ◽  
Semiconducting Materials ◽  
Blend Films ◽  
Moderate Power ◽  
Lowest Unoccupied Molecular Orbital ◽  
Cyano Groups ◽  
Conversion Efficiencies

The incorporation of electron-accepting units into the π-conjugated systems can allow the modulation of the physical properties and frontier orbital energy levels of the molecules. An electron-accepting π-conjugated compound (CNNTz-TR) containing cyano-substituted naphthobisthiadiazole (CNNTz) was synthesized via a nucleophilic substitution reaction as the key step. Owing to the presence of the cyano groups, CNNTz-TR afforded a low-lying lowest unoccupied molecular orbital energy level. Organic solar cells based on the blend films of CNNTz-TR and a low-bandgap donor exhibited moderate power conversion efficiencies. The result showed that embedding the CNNTz unit into the π-conjugated backbone was an effective approach for designing electron-accepting semiconducting materials.

scholarly journals Emphasizing the Operational Role of a Novel Graphene-Based Ink into High Performance Ternary Organic Solar Cells

2019 ◽  
Author(s):  
Minas M. Stylianakis ◽  
Dimitriοs M. Kosmidis ◽  
Katerina Anagnostou ◽  
Christos Polyzoidis ◽  
Miron Krassas ◽  
...  
Keyword(s):  
Solar Cells ◽  
Molecular Orbital ◽  
Organic Solar Cells ◽  
High Performance ◽  
Energy Levels ◽  
Fullerene Derivative ◽  
Highest Occupied Molecular Orbital ◽  
Lowest Unoccupied Molecular Orbital ◽  
Synthetic Routes

A novel solution-processed graphene-based material was synthesized by treating graphene oxide (GO) with 2,5,7-trinitro-9-oxo-fluorenone-4-carboxylic acid (TNF-COOH) moieties, via simple synthetic routes. The yielded molecule N-[(carbamoyl-GO)ethyl]-N’-[(carbamoyl)-(2,5,7-trinitro-9-oxo-fluorene)] (GO-TNF) was thoroughly characterized and it was shown that it presents favorable highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels to function as a bridge component between the polymeric donor poly({4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl}{3-fluoro-2-[(2-ethylhexyl)carbonyl] thieno[3,4-b]thiophenediyl}) (PTB7) and the fullerene derivative acceptor [6,6]-phenyl-C71-butyric-acid-methylester (PC71BM). In this context, a GO-TNF based ink was prepared and directly incorporated within the binary photoactive layer, in different volume ratios (1-3% ratio to the blend), for the effective realization of inverted ternary organic solar cells (OSCs) of the structure ITO/PFN/PTB7:GO-TNF:PC71BM/MoO3/Al. The addition of 2% v/v GO-TNF ink led to a champion power conversion efficiency (PCE) of 8.71% that was enhanced by ~13% as compared to the reference cell.

scholarly journals D-A-D structured organic molecules with diketopyrrolopyrrole acceptor unit for solution-processed organic solar cells

2014 ◽  
Vol 372 (2013) ◽  
pp. 20130009 ◽  
Author(s):  
Jing Zhang ◽  
Chang He ◽  
Zhi-Guo Zhang ◽  
Dan Deng ◽  
Maojie Zhang ◽  
...  
Keyword(s):  
Solar Cells ◽  
Organic Solar Cells ◽  
Organic Molecules ◽  
Bulk Heterojunction ◽  
Energy Levels ◽  
Orbital Energy ◽  
Broad Absorption ◽  
Photovoltaic Properties ◽  
Solution Processed ◽  
Highest Occupied Molecular Orbital

Four solution-processable D-A-D structured organic molecules with diketopyrrolopyrrole (DPP) as acceptor unit and triphenylamine (TPA) or (4-hexyl)thieno [3,2-b]thiophene (HTT) as donor unit, DPP8-TPA, DPP8-TPA-OR, DPP6-HTT and DPP8-HTT, were designed and synthesized for the application as donor materials in solution-processed organic solar cells (OSCs). The molecules show broad absorption and relatively lower highest occupied molecular orbital energy levels. Photovoltaic properties of the molecules were investigated by fabricating the bulk-heterojunction OSCs with the molecules as donor and PC 71 BM as acceptor. Power conversion efficiency of the OSC based on DPP8-HTT reached 1.5% under the illumination of AM1.5, 100 mW cm −2 .

A–D–A-type S,N-heteropentacene-based hole transport materials for dopant-free perovskite solar cells

2015 ◽  
Vol 3 (34) ◽  
pp. 17738-17746 ◽  
Author(s):  
Christopher Steck ◽  
Marius Franckevičius ◽  
Shaik Mohammed Zakeeruddin ◽  
Amaresh Mishra ◽  
Peter Bäuerle ◽  
...  
Keyword(s):  
Solar Cells ◽  
Energy Levels ◽  
Power Conversion ◽  
Perovskite Solar Cells ◽  
Hole Transport ◽  
Orbital Energy ◽  
Frontier Orbital ◽  
Conversion Efficiencies ◽  
Frontier Orbital Energy

Heteropentacene-based A–D–A type hole transport materials with suitable frontier orbital energy levels were synthesized and used in perovskite solar cells showing power conversion efficiencies up to 11.4%.

scholarly journals An Effective D-π-A Type Donor Material Based on 4-Fluorobenzoylacetonitrile Core Unit for Bulk Heterojunction Organic Solar Cells

2021 ◽  
Vol 11 (2) ◽  
pp. 646
Author(s):  
Shabaz Alam ◽  
M. Shaheer Akhtar ◽  
Abdullah ◽  
Eun-Bi Kim ◽  
Hyung-Shik Shin ◽  
...  
Keyword(s):  
Solar Cells ◽  
Molecular Orbital ◽  
Organic Solar Cells ◽  
High Performance ◽  
Bulk Heterojunction ◽  
Energy Levels ◽  
Photovoltaic Properties ◽  
Donor Material ◽  
Highest Occupied Molecular Orbital ◽  
Lowest Unoccupied Molecular Orbital

In order to develop new and effective donor materials, a planar donor-π-acceptor (D-π-A) type small organic molecule (SOM), 2-(4-fluorobenzoyl)-3-(5″-hexyl-[2,2′:5′,2″-terthiophen]-5-yl) acrylonitrile, named as H3T-4-FOP, was synthesized by the reaction of 4-fluorobenzoylacetonitrile (as acceptor unit) and hexyl terthiophene (as donor unit) derivatives. Promising optical, solubility, electronic and photovoltaic properties were observed for the H3T-4-FOP SOM. Significantly, the presence of 4-fluorobenzoylacetonitrile as an acceptor unit in H3T-4-FOP SOM tuned the optical band gap to ~2.01 eV and procured the reasonable energy levels as highest occupied molecular orbital (HOMO) of −5.27 eV and lowest unoccupied molecular orbital (LUMO) −3.26 eV. The synthesized H3T-4-FOP SOM was applied as a donor material to fabricate solution-processed bulk heterojunction organic solar cells (BHJ-OSCs) with an active layer of H3T-4-FOP: PC61BM (1:2, w/w) and was validated as having a good power conversion efficiency (PCE) of ~4.38%. Our studies clearly inspire for future designing of multifunctional groups containing the 4-fluorobenzoylacetonitrile based SOM for high performance BHJ-OSCs.

scholarly journals A-D-A-Type Oligothiophenes Containing Benzothiadiazole Terminal Units for Small Molecule Organic Solar Cells

2014 ◽  
Vol 2 (1) ◽  
Author(s):  
Simon Steinberger ◽  
Amaresh Mishra ◽  
Gisela Schulz ◽  
Christian Uhrich ◽  
Martin Pfeiffer ◽  
...  
Keyword(s):  
Solar Cells ◽  
Organic Solar Cells ◽  
Bulk Heterojunction ◽  
Power Conversion ◽  
Visible Spectrum ◽  
Photovoltaic Properties ◽  
Acceptor Group ◽  
Moderate Power ◽  
Conversion Efficiencies ◽  
Homo Lumo

AbstractThe electron-deficient, fused-heterocyclebenzo[c][1,2,5]thiadiazole (BTDA) is investigated as acceptor group in A-D-A-type oligothiophenes in order to correlate their relative acceptor strength with opto-electronic and photovoltaic properties. In this respect, two novel BDTA-capped oligothiopheneswere synthesized and characterized by optical and electrochemical measurements. They showed broad absorptions in the visible spectrum and HOMO-LUMO energies well suited for organic solar cells. The attachment of terminal BTDA acceptor units to the conjugated oligothiophene backbone resulted in a hypsochromic shift in UV-Vis absorption and larger band gap in comparison to previously reported analogous dicyanovinylene (DCV)-substituted oligothiophenes indicating that BDTA is a weaker acceptor than DCV. Vacuumprocessed m-i-p (metal-intrinsic-p-doped)-type bilayer solar cells using these co-oligomers as donor and C60 as acceptor gave moderate power conversion efficiencies of around 1.0%. Bulk-heterojunction (BHJ) solar cells prepared by solution-processing using fullerene PC61BM as acceptor generated slightly lower efficiencies of 0.9%, whichwere increased to 1.5% by using the higher fullerene PC71BM. It was found that the cell efficiencies were mostly limited by the low photocurrent densities due to moderate light absorption in the bilayer devices and low fill factors coming from inefficient charge transport in the solutionprocessed BHJ devices.

High open circuit voltage organic solar cells based upon fullerene free bulk heterojunction active layers

2014 ◽  
Vol 92 (10) ◽  
pp. 932-939 ◽  
Author(s):  
Ala’a F. Eftaiha ◽  
Jon-Paul Sun ◽  
Arthur D. Hendsbee ◽  
Casper Macaulay ◽  
Ian G. Hill ◽  
...  
Keyword(s):  
Solar Cells ◽  
Organic Solar Cells ◽  
Open Circuit Voltage ◽  
Field Effect Transistors ◽  
Bulk Heterojunction ◽  
Energy Levels ◽  
Open Circuit ◽  
Frontier Molecular Orbital ◽  
Orbital Energy ◽  
High Electron

We have recently reported on a small organic molecule containing a bithiophene core with end-capping phthalimide units (PthTh2Pth) that exhibited a H-aggregation tendency in the solid state and high electron mobility in organic field effect transistors. In this contribution, we have studied both the physical and electrical properties of poly(3-hexylthiophene) (P3HT) and PthTh2Pth thin films by measuring the optical absorption, Frontier molecular orbital energy levels, photoluminescence quenching, thermal properties, and photovoltaic response. Our results have provided a useful insight into the use of PthTh2Pth as an electron acceptor material for organic photovoltaic applications. In comparison with high-performance, fullerene-based, solution-processed bulk heterojunction solar cells reported in the literature, a relatively high open circuit voltage (∼0.94 V) was obtained for various donor–acceptor blend ratios. These results highlight the potential for PthTh2Pth to act as an alternative to fullerenes as acceptors in organic solar cell devices.

Nonfullerene Electron Acceptors with Electron-deficient Units Containing Cyano Groups for Organic Solar Cells

2021 ◽  
Author(s):  
Bing Lu ◽  
Zhecheng Zhang ◽  
Jian Wang ◽  
Guilong Cai ◽  
Yue Ding ◽  
...  
Keyword(s):  
Solar Cells ◽  
Organic Solar Cells ◽  
Power Conversion ◽  
Electron Acceptors ◽  
Single Junction ◽  
Cyano Groups ◽  
Conversion Efficiencies

The performance of organic solar cells based on nonfullerene acceptors is improving rapidly, and nowadays the power conversion efficiencies of single-junction devices have achieved over 18%. Nonfullerene acceptors usually consist...

scholarly journals Emphasizing the Operational Role of a Novel Graphene-Based Ink into High Performance Ternary Organic Solar Cells

Nanomaterials ◽  
2020 ◽  
Vol 10 (1) ◽  
pp. 89 ◽  
Author(s):  
Minas M. Stylianakis ◽  
Dimitrios M. Kosmidis ◽  
Katerina Anagnostou ◽  
Christos Polyzoidis ◽  
Miron Krassas ◽  
...  
Keyword(s):  
Solar Cells ◽  
Molecular Orbital ◽  
Organic Solar Cells ◽  
High Performance ◽  
Energy Levels ◽  
Fullerene Derivative ◽  
Highest Occupied Molecular Orbital ◽  
Lowest Unoccupied Molecular Orbital ◽  
Synthetic Routes

A novel solution-processed, graphene-based material was synthesized by treating graphene oxide (GO) with 2,5,7-trinitro-9-oxo-fluorenone-4-carboxylic acid (TNF-COOH) moieties, via simple synthetic routes. The yielded molecule N-[(carbamoyl-GO)ethyl]-N′-[(carbamoyl)-(2,5,7-trinitro-9-oxo-fluorene)] (GO-TNF) was thoroughly characterized and it was shown that it presents favorable highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels to function as a bridge component between the polymeric donor poly({4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl}{3-fluoro-2-[(2-ethylhexyl)carbonyl] thieno[3,4-b]thiophenediyl}) (PTB7) and the fullerene derivative acceptor [6,6]-phenyl-C71-butyric-acid-methylester (PC71BM). In this context, a GO-TNF based ink was prepared and directly incorporated within the binary photoactive layer, in different volume ratios (1%–3% ratio to the blend) for the effective realization of inverted ternary organic solar cells (OSCs) of the structure ITO/PFN/PTB7:GO-TNF:PC71BM/MoO3/Al. The addition of 2% v/v GO-TNF ink led to a champion power conversion efficiency (PCE) of 8.71% that was enhanced by ~13% as compared to the reference cell.

Nonfullerene acceptors for P3HT-based organic solar cells

2021 ◽  
Author(s):  
Shreyam Chatterjee ◽  
Seihou JINNAI ◽  
Yutaka Ie
Keyword(s):  
Solar Cells ◽  
High Power ◽  
Organic Solar Cells ◽  
Power Conversion ◽  
Conversion Efficiencies

Progressive advancement of remarkably high power conversion efficiencies (PCEs) of organic solar cells (OSCs) largely depends on the development of norfullerene acceptors (NFAs), revealing stupendous ability of OSCs to shift...

scholarly journals The Effects of Molecular Packing Behavior of Small-Molecule Acceptors in Ternary Organic Solar Cells

2021 ◽  
Vol 11 (2) ◽  
pp. 755
Author(s):  
Eunhee Lim
Keyword(s):  
Solar Cells ◽  
Energy Level ◽  
Ternary System ◽  
Small Molecule ◽  
Organic Solar Cells ◽  
Orbital Energy ◽  
Working Mechanism ◽  
Energy Level Structure ◽  
The Third ◽  
Molecular Backbone

Herein, two diketopyrrolopyrrole (DPP)-based, small-molecule isomers, o- and p-DPP-PhCN, were introduced as acceptors in ternary organic solar cells (OSCs). The isomers have the same molecular backbone but differ in the positions of the cyanide (CN) substituents (ortho and para), which greatly affects their packing behavior. Ternary solar cells composed of poly(3-hexylthiophene) (P3HT):DPP-PhCN:phenyl-C61-butyric acid methyl ester (PCBM) were fabricated, and the effects of the different packing behaviors of the third component on the device performance and the working mechanism of the ternary cells were investigated. The addition of o-DPP-PhCN with a relatively high-lying lowest unoccupied molecular orbital energy level resulted in an increase in the open-circuit voltage (VOC) in the ternary devices, demonstrating the alloy-like structure of the two acceptors (o-DPP-PhCN and PCBM) in the ternary system. However, the p-DPP-PhCN-based ternary cells exhibited VOC values similar to that of a P3HT:PCBM binary cell, irrespective of the addition of p-DPP-PhCN, indicating a cascade energy-level structure in the ternary system and an effective charge transfer from the P3HT to the PCBM. Importantly, by increasing the addition of p-DPP-PhCN, the short-circuit current density increased substantially, resulting in pronounced shoulder peaks in the external quantum efficiency responses in the long-wavelength region, corresponding to the contribution of the photocurrent generated by the light absorption of p-DPP-PhCN. Despite sharing the same molecular backbone, the two DPP-PhCNs exhibited substantially different packing behaviors according to the position of their CN substituents, which also greatly affected the working mechanism of the ternary devices fabricated using the DPP-PhCNs as the third component.

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