- Anthradithiophene-benzothiadiazole-based small molecule donors for organic solar cells
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A new A-D-A small molecule involving anthradithiophene as a donor and benzothiadiazole as an acceptor unit has been synthesized by Stille coupling reaction. Its thermal, optical and electronic properties, hole mobility and photovoltaic properties have been fully characterized. The resulting material shows a broad absorption range (300-750 nm), a low band gap (1.59 eV) and a moderate hole mobility (8.81 × 10-4 cm2 V -1 s-1). We used the new small molecule blended with PC71BM as the active layer to fabricate solution-processed organic solar cells (OSCs), and employed a variety of post-treatment methods to optimize the device performance. With the help of polar solvent exposure, the highest power conversion efficiency (PCE) of 0.55% was obtained. These results would supply useful information to understand the relationship between molecular structure and photovoltaic properties of anthradithiophene/benzothiadiazole- based OSCs.
- Liu, Qida,Liu, Ying,Wang, Yang,Ai, Ling,Ouyang, Xinhua,Han, Lei,Ge, Ziyi
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- Solvent boiling point affects the crystalline properties and performances of anthradithiophene-based devices
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We investigated the effects of the solvent boiling point on organic field-effect transistor (OFET) device performances in devices prepared using two newly synthesized anthradithiophene derivatives: 9,10-di(4′-pentylphenylethynyl)-anthra[2,3-b:6,7-b′]dithiophene (DPPEADT) and 9,10-bi([9′,9′-dimethyl-fluoren-2-ylethynyl])-anthra[2,3-b:6,7-b′]dithiophene (DFEADT). DPPEADT exhibited a distinct crystalline morphology whereas DFEADT was amorphous. We characterized the relationship between the molecular structures, film morphologies, and OFET device performances in devices prepared using solvents having one of three different boiling points (chlorobenzene, 1,2-dichlorobenzene, and 1,2,4-trichlorobenzene). 1,2,4-Trichlorobenzene, which provided the highest boiling point among the solvents tested and acted as a good solvent for DPPEADT, significantly improved the field-effect mobilities of DPPEADT devices up to 0.16 cm2/V by enhancing the crystallinity of the film. OFETs based on amorphous DFEADT films prepared using the three solvents did not provide enhanced electrical performances. The differences between the transistor performances were attributed to the degree of π-overlap, the molecular structures, and the morphological properties of the films.
- An, Tae Kyu,Park, Seong Jong,Ahn, Eun Soo,Jang, Sang Hun,Kim, Yebyeol,Kim, Kyunghun,Cha, Hyojung,Kim, Yu Jin,Kim, Se Hyun,Park, Chan Eon,Kim, Yun-Hi
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- Resistance to unwanted photo-oxidation of multi-acene molecules
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Although long acenes remain a key class of π- conjugated molecules for numerous applications, photoinduced oxidation upon exposure of the acene to light, often through sensitization of 1O2, is an important reaction requiring mitigation for most applications. In response to this ongoing challenge, this paper presents a series of four new diarylethynyl-substituted long acenes-three tetracenes and one anthradithiophene-in which the arylene pendants are either benzene, naphthalene, or anthracene. UV/vis and fluorescence spectroscopy reveals that the anthracene-substituted derivatives fluoresce poorly (φ 0.01). Although all four long acenes react with 1O2 at expected rates when an external photosensitizer is included and show the expected changes in fluorescence to accompany these reactions, the anthracene-substituted derivatives resist direct photoinduced oxidation. Through a combination of mechanistic experiments, we conclude that rapid nonradiative decay of the anthracene-substituted derivatives, perhaps because of inter-arene torsions that emerge in theoretical geometry optimizations, makes these compounds poor photosensitizers for 1O2 or other reactive oxygen species. This discovery opens new design possibilities for extended acene structures with improved photochemical stability.
- Thomas, Samuel W. Iii,Yan, Yu,Lamport, Zachary A.,Kymissis, Ioannis
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- Organic Dye and Dye-Sensitized Solar Cell
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PURPOSE: An organic dye, photoelectric diode including the same and dye-sensitized solar battery are provided to have an absorbing band in long wavelength. CONSTITUTION: An organic dye is represented by chemical formula 1. A photoelectric diode includes porous oxide semiconductor membrane which includes the organic dye. A dye-sensitized solar cell comprises a first electrode, a second electrode which is formed on one side of the first electrode and includes a light absorptive layer, and electrolyte buried in a space between the first and second electrodes.
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Paragraph 0328-0334
(2018/02/10)
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- SYNTHESIS OF NEW SMALL MOLECULES/OLIGOMERS WITH HIGH CONDUCTIVITY AND ABSORPTION FOR OPTOELECTRONIC APPLICATION
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Disclosed are semiconducting or conducting organic small molecules and oligomers that contain a central, electron rich, functionalized dihydrodicyclopentylanthracene core (or electron donor core) that is connected to at least one or two comparatively electron deficient monomeric unit or units (or electron acceptor units) that feature group 16 heteroatoms sulfur, selenium or tellurium or combinations thereof. Multiple electron rich cores can be linked together through one or more alkynyl linkages. The small molecules and oligomers can have the following generic structure and can be used in areas such as organic photovoltaic materials..
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Paragraph 0061
(2015/11/23)
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- Low band-gap D-A conjugated copolymers based on anthradithiophene and diketopyrrolopyrrole for polymer solar cells and field-effect transistors
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Two conjugated copolymers PADT-DPP and PADT-FDPP based on anthradithiophene and diketopyrrolopyrrole, with thiophene and furan as the π-conjugated bridge, respectively, were successfully synthesized and characterized. The number-averaged molecular weights of the two polymers are 38.7 and 30.2 kg/mol, respectively. Polymers PADT-DPP and PADT-FDPP exhibit broad absorption bands and their optical band gaps are 1.44 and 1.50 eV, respectively. The highest occupied molecular orbital energy level of PADT-DPP is located at -5.03 eV while that of PADT-FDPP is at -5.16 eV. In field-effect transistors, PADT-DPP and PADT-FDPP displayed hole mobilities of 4.7 × 10-3 and 2.7 × 10-3 cm2/(V s), respectively. In polymer solar cells, PADT-DPP and PADT-FDPP showed power conversion efficiency (PCE) of 3.44% and 0.29%, respectively. Atomic force microscopy revealed that the poor efficiency of PADT-FDPP should be related to the large two-phase separation in its active layer. If 1,8-diiodooctane (DIO) was used as the solvent additive, the PCE of PADT-DPP remained almost unchanged due to very limited morphology variation. However, the addition of DIO could remarkably elevate the PCE of PADT-FDPP to 2.62% because of the greatly improved morphology. Our results suggest that the anthradithiophene as an electron-donating polycyclic system is useful to construct new D-A alternating copolymers for efficient polymer solar cells.
- Huang, Jun,Zhu, Yongxiang,Zhang, Lianjie,Cai, Ping,Xu, Xiaofeng,Chen, Junwu,Cao, Yong
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p. 1652 - 1661
(2014/05/20)
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- Assembly and fiber formation of a gemini-type hexathienocoronene amphiphile for electrical conduction
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We report the synthesis, characterization, and self-assembly of a new gemini-type amphiphilic hexathienocoronene (HTCGemini), which owes its amphiphilicity to two hydrophobic dodecyl chains on one side of the HTC core and two hydrophilic triethylene glycol (TEG) chains on the other. Bearing a softer aromatic HTC core than the conventional hexa-peri- hexabenzocoronenes (HBC), and being more planar than contorted- hexabenzocoronenes (c-HBC), HTCGemini is demonstrated to yield various well-ordered assemblies in solution, at the liquid-solid interface, and in solid state by the use of different processing techniques. Regular fibers, helices, and tubes can be formed simply by processing from different solvents. At the liquid-solid interface, as visualized by scanning tunneling microscopy (STM), pairs of molecules adsorb very close to each other and arrange in the p2 plane group, driven by packing constraints and weak van der Waals interactions between adjacent molecules. HTCGemini also exhibits phase forming behavior in the bulk upon thermal treatment, resulting in a crystalline, herringbone-like columnar structure. Owning to an electron enriched aromatic core with respect to other reported coronenes, HTCGemini easily forms a stable radical cation, both in solution and in the bulk, upon oxidative doping with nitrosonium tetrafluoroborate (NOBF4). Furthermore, light irradiation of the blend film of HTCGemini and phenyl-C 61-butyric acid methyl ester (PCBM) generates a prominent photocurrent which can be switched repeatedly with a large on/off ratio (6.0 × 104). The self-assembled structures obtained from HTC Gemini at different length scales have potential applications in optoelectronic devices, solar cells, and redox sensors.
- Chen, Long,Mali, Kunal S.,Puniredd, Sreenivasa R.,Baumgarten, Martin,Parvez, Khaled,Pisula, Wojciech,De Feyter, Steven,Muellen, Klaus
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supporting information
p. 13531 - 13537
(2013/09/24)
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- Hexathienocoronenes: Synthesis and self-organization
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Here we report hexathienocoronenes (HTCs), fully thiophene-annelated coronenes in which six double bonds in the periphery are thieno-fused. The derivatives tetrasubstituted with hexyl and dodecyl chains show a phase formation that strongly depends on the chain length. HTCs are remarkably stronger donors than the known thiophene-annelated coronenes but do not readily assemble into well-ordered films when deposited from the vapor phase. Thus, thin-film transistors fabricated by vacuum deposition have only modest field-effect mobilities of 0.002 cm2 V-1 s-1.
- Chen, Long,Puniredd, Sreenivasa R.,Tan, Yuan-Zhi,Baumgarten, Martin,Zschieschang, Ute,Enkelmann, Volker,Pisula, Wojciech,Feng, Xinliang,Klauk, Hagen,Muellen, Klaus
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supporting information
p. 17869 - 17872
(2013/01/15)
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- Stable, crystalline acenedithiophenes with up to seven linearly fused rings
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(Chemical Equation Presented) We report the synthesis of a series of crystalline acenedithiophenes with up to seven linearly fused rings and silylethynyl substituents. These functional groups are designed to both improve solubility and enhance cofacial interactions in the solid. We discuss the crystal packing of these materials, as well as their physical properties such as oxidation potential, UV-vis absorption, fluorescence emission, and decomposition pathways.
- Payne, Marcia M.,Odom, Susan A.,Parkin, Sean R.,Anthony, John E.
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p. 3325 - 3328
(2007/10/03)
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