- n-Type Semiconducting Naphthalene Diimide-Perylene Diimide Copolymers: Controlling Crystallinity, Blend Morphology, and Compatibility Toward High-Performance All-Polymer Solar Cells
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Knowledge of the critical factors that determine compatibility, blend morphology, and performance of bulk heterojunction (BHJ) solar cells composed of an electron-accepting polymer and an electron-donating polymer remains limited. To test the idea that bulk crystallinity is such a critical factor, we have designed a series of new semiconducting naphthalene diimide (NDI)-selenophene/perylene diimide (PDI)-selenophene random copolymers, xPDI (10PDI, 30PDI, 50PDI), whose crystallinity varies with composition, and investigated them as electron acceptors in BHJ solar cells. Pairing of the reference crystalline (crystalline domain size Lc = 10.22 nm) NDI-selenophene copolymer (PNDIS-HD) with crystalline (Lc = 9.15 nm) benzodithiophene-thieno[3,4-b]thiophene copolymer (PBDTTT-CT) donor yields incompatible blends, whose BHJ solar cells have a power conversion efficiency (PCE) of 1.4%. However, pairing of the new 30PDI with optimal crystallinity (Lc = 5.11 nm) as acceptor with the same PBDTTT-CT donor yields compatible blends and all-polymer solar cells with enhanced performance (PCE = 6.3%, Jsc = 18.6 mA/cm2, external quantum efficiency = 91%). These photovoltaic parameters observed in 30PDI:PBDTTT-CT devices are the best so far for all-polymer solar cells, while the short-circuit current (Jsc) and external quantum efficiency are even higher than reported values for [70]-fullerene:PBDTTT-CT solar cells. The morphology and bulk carrier mobilities of the polymer/polymer blends varied substantially with crystallinity of the acceptor polymer component and thus with the NDI/PDI copolymer composition. These results demonstrate that the crystallinity of a polymer component and thus compatibility, blend morphology, and efficiency of polymer/polymer blend solar cells can be controlled by molecular design. (Figure Presented).
- Hwang, Ye-Jin,Earmme, Taeshik,Courtright, Brett A. E.,Eberle, Frank N.,Jenekhe, Samson A.
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- Diseleno[2,3-b:3′,2′-d]selenophene and Diseleno[2,3-b:3′,2′-d] thiophene: Building Blocks for the Construction of [7]Helicenes
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New building blocks, 2,5-di(trimethylsilanyl)diseleno[2,3-b:3′,2′-d]selenophene ((TMS)2-DSS) and 2,5-di(trimethylsilanyl)diseleno[2,3-b:3′,2′-d]thiophene ((TMS)2-DST), for helicenes were obtained from selenophene with total yields of 54 and 61%. From (TMS)2-DSS and (TMS)2-DST, selenophene-based hetero[7]helicenes, 5,5′-di(trimethylsilanyl)benzo[1,2-b:3,4-b′]bis(diseleno[2,3-b:3′,2′-d]thiophene) (rac-1), and 5,5′-di(trimethylsilanyl)benzo[1,2-b:3,4-b′]bis(diseleno[2,3-b:3′,2′-d]selenophene) (rac-2) were prepared. The overall yields from selenophene were approximately 6.5 and 6.1%, respectively. Intermolecular interactions such as C-Se, C-S, and Se-Se were observed in the crystal packings of rac-1 and rac-2. In addition, the absorption behaviors of rac-1 and rac-2 were investigated.
- Xu, Wan,Wu, Longlong,Fang, Maohong,Ma, Zhiying,Shan, Zhen,Li, Chunli,Wang, Hua
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- Synthesis of a 4,9-Didodecyl Angular-Shaped Naphthodiselenophene Building Block to Achieve High-Mobility Transistors
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A new tetracyclic 4,9-dialkyl angular-shaped naphthodiselenophene (4,9-α-aNDS) was designed and synthesized. The naphthalene core in 4,9-α-aNDS is formed by the DBU-induced 6π-cyclization of an (E)-1,2-bis(3-(tetradec-1-yn-1-yl)selenophen-2-yl)ethene intermediate followed by the second PtCl2-catalyzed benzannulation. This synthetic protocol allows for incorporating two dodecyl groups regiospecifically at 4,9-positions of the resulting α-aNDS. An ordered supramolecular self-assembly formed via noncovalent selenium-selenium interactions with a short contact of 3.5 ? was observed in the single-crystal structure of 4,9-α-aNDS. The distannylated α-aNDS building block was copolymerized with Br-DTFBT and Br-DPP acceptors by Stille cross coupling to form two new donor-acceptor polymers PαNDSDTFBT and PαNDSDPP, respectively. The bottom-gate/top-contact organic field-effect devices using the PαNDSDTFBT and PαNDSDPP semiconductors accomplished superior hole mobility of 3.77 and 2.17 cm2 V-1 s-1, respectively, which are among the highest mobilities reported to date.
- Tsai, Che-En,Yu, Ruo-Han,Lin, Fang-Ju,Lai, Yu-Ying,Hsu, Jhih-Yang,Cheng, Sheng-Wen,Hsu, Chain-Shu,Cheng, Yen-Ju
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- All-polymer solar cells with 3.3% efficiency based on naphthalene diimide-selenophene copolymer acceptor
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The lack of suitable acceptor (n-type) polymers has limited the photocurrent and efficiency of polymer/polymer bulk heterojunction (BHJ) solar cells. Here, we report an evaluation of three naphthalene diimide (NDI) copolymers as electron acceptors in BHJ solar cells which finds that all-polymer solar cells based on an NDI-selenophene copolymer (PNDIS-HD) acceptor and a thiazolothiazole copolymer (PSEHTT) donor exhibit a record 3.3% power conversion efficiency. The observed short circuit current density of 7.78 mA/cm 2 and external quantum efficiency of 47% are also the best such photovoltaic parameters seen in all-polymer solar cells so far. This efficiency is comparable to the performance of similarly evaluated [6,6]-Phenyl-C 61-butyric acid methyl ester (PC60BM)/PSEHTT devices. The lamellar crystalline morphology of PNDIS-HD, leading to balanced electron and hole transport in the polymer/polymer blend solar cells accounts for its good photovoltaic properties.
- Earmme, Taeshik,Hwang, Ye-Jin,Murari, Nishit M.,Subramaniyan, Selvam,Jenekhe, Samson A.
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- Stepwise enhancement on optoelectronic performances of polyselenophene via electropolymerization of mono-, bi-, and tri-selenophene
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Although much progress have been made on polyselenophenes-based molecular systems, the poor optoelectronic performance of parent polyselenophene still hamper both the fundamental understanding and practical applications of such materials due to the monomer instability during the polymerization process and the lack of suitable monomeric precursors. In this work, we develop an effective method to improve the optoelectronic performances and stability of parent polyselenophene by stepwise increasing the initial monomeric chain length for electrochemical polymerization. We find that the chain length increment of the monomeric structures from selenophene to bi- and tri-selenophenes dramatically reduces the electropolymerization potential and thus enables the formation of high quality polyselenophene films with better conjugated structures and less structural defects. As-formed polyselenophene from tri-selenophene reveals lowered optical band gap (1.72 eV), better redox activity and stability, and significantly improved electrochromic nature of reversible and stable color changes between red and blue with high performance including superior optical contrast up to 75%, high coloration efficiency up to 450 cm2 C?1, and very fast switching time (0.7 s for oxidation and 0.4 s for reduction). These advantageous properties of as-prepared polyselenophene films afford the successful fabrication of patterned flexible electrochromic devices, which exhibit reversible and stable color changes upon both doping-dedoping and mechanical bending.
- Hu, Faqi,Jian, Nannan,Liu, Ximei,Lu, Baoyang,Qu, Kai,Xu, Jingkun,Zhao, Guoqun
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- Photosensitizer, and preparation method and applications thereof
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The invention belongs to the technical field of light power treatment, and more specifically relates to a photosensitizer, and a preparation method and applications thereof. The photosensitizer is a compound with a structure represented by formula I. Acco
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Paragraph 0027; 0028
(2019/01/08)
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- COMPOUND, COMPOSITION, ORGANIC SEMICONDUCTOR DEVICE, AND METHOD FOR PRODUCING COMPOUND
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PROBLEM TO BE SOLVED: To provide a compound, a composition, an organic semiconductor device and a method for producing a compound which make it possible to reduce an absolute value of threshold voltage without reducing carrier mobility. SOLUTION: The present invention provides a compound represented by formula (1) (X is Se or Te). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0100; 0102
(2018/02/21)
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- Selenophenes: Introducing a New Element into the Core of Non-Steroidal Estrogen Receptor Ligands
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The importance of the heterocyclic core elements with peripheral phenolic and alkyl substituents as a dominant structural motif of ligands for the estrogen receptor (ER) has been well recognized. In this study we expanded the structural diversity of core
- Zhang, Silong,Wang, Zhiyong,Hu, Zhiye,Li, Changhao,Tang, Chu,Carlson, Kathryn E.,Luo, Junjie,Dong, Chune,Katzenellenbogen, John A.,Huang, Jian,Zhou, Hai-Bing
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supporting information
p. 235 - 249
(2017/02/15)
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- Selenophen compound
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The invention belongs to the technical field of medicines and in particular discloses a selenophen compound which takes an estrogen receptor as a target point, has resistance to hormone-dependent (positive ER+) breast cancer and also has high inhibitory a
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Paragraph 0010
(2016/10/08)
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- Molecular engineering of starburst triarylamine donor with selenophene containing π-linker for dye-sensitized solar cells
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A series of new D-π-A organic photosensitizers 7a-7d featuring a novel starburst electron donor unit and uncommon selenophene containing π-linker were synthesized, characterized, and applied for fabrication of dye-sensitized solar cells (DSSCs). Dyes 11d-
- Ho, Po-Yu,Siu, Chi-Ho,Yu, Wai-Hong,Zhou, Panwang,Chen, Tao,Ho, Cheuk-Lam,Lee, Lawrence Tien Lin,Feng, Ying-Hsuan,Liu, Jianyong,Han, Keli,Lo, Yih Hsing,Wong, Wai-Yeung
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p. 713 - 726
(2016/02/03)
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- Molecular dipole, dye structure and electron lifetime relationship in efficient dye sensitized solar cells based on donor-π-acceptor organic sensitizers
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In this work we report the synthesis and characterization of two new push-pull organic dyes (LC95 and LC107) to be employed as sensitizers in solar cells. Both molecules contain the bis(4-hexyloxyphenylamino)styril unit as the donor group, the cyanoacrylate acid as the acceptor, and the selenophene-thiophene (LC95 dye) and thiophene-selenophene (LC107 dye) moieties as the conjugated linkers. Dye sensitized solar cells employing these two photosensitizers and the cobalt(II/III) redox electrolyte exhibit good solar to energy conversion efficiencies of 6.3% and 6.5% measured under the 100 mW cm-2simulated AM1.5 sunlight. The efficiencies are slightly lower with the iodine/iodide electrolyte. The performance of these two dyes has been discussed and compared to three closely related sensitizers, i.e. C214, C216 and C218, by means of experimental measurements and quantum chemistry computations, with special attention to differences on their geometries, molecular dipoles and electron recombination lifetimes.
- Climent, Clàudia,Cabau, Lydia,Casanova, David,Wang, Peng,Palomares, Emilio
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p. 3162 - 3172
(2015/02/19)
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- Side chain engineering of n-type conjugated polymer enhances photocurrent and efficiency of all-polymer solar cells
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Side chain engineering of an n-type polymer provides a means of maintaining solubility while increasing crystallinity and electron mobility, leading to enhanced photocurrent. Bulk heterojunction solar cells composed of a side chain engineered copolymer (PNDIS-30BO) as acceptor and PSEHTT as donor give 10.4 mA cm-2 photocurrent and 4.4% efficiency. the Partner Organisations 2014.
- Hwang, Ye-Jin,Earmme, Taeshik,Subramaniyan, Selvam,Jenekhe, Samson A.
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supporting information
p. 10801 - 10804
(2014/11/08)
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- Thiophene and selenophene donor-acceptor polyimides as polymer electrets for nonvolatile transistor memory devices
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We report the nonvolatile memory characteristics of n-type N,N'-bis(2-phenylethyl)perylene-3,4:9,10-tetracarboxylic diimide (BPE-PTCDI) based organic field-effect transistors (OFET) using the polyimide electrets of poly[2,5-bis(4-aminophenylenesulfanyl)se
- Chou, Ying-Hsuan,Lee, Wen-Ya,Chen, Wen-Chang,You, Nam-Ho,Kurosawa, Tadanori,Higashihara, Tomoya,Ueda, Mitsuru
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p. 6946 - 6956,11
(2020/08/24)
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- Dicyanovinylene-substituted selenophene-thiophene co-oligomers for small-molecule organic solar cells
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We report on the design, synthesis, and characterization of a series of terminal dicyanovinylene-substituted quinquechalcogenophenes as light-harvesting small-molecule donor materials for organic solar cells. The spectroscopic, electrochemical, and thermal properties of these pentamers were investigated. The replacement of thiophene unit(s) by selenophene(s) results in a bathochromic shift of the longest wavelength absorption band with concomitant increase of the molar extinction coefficient. Cyclic voltammetry measurements revealed fully reversible oxidation and irreversible reduction processes. The highest occupied and lowest unoccupied molecular orbital (HOMO/LUMO) energy levels were determined from electrochemical measurements and lie in the range of -5.6 and -3.8 eV. Vacuum-deposited bulk-heterojunction solar cells fabricated with the novel chalcogenophenes as donor and C60 as acceptor displayed high open-circuit voltages of up to 1 V, short-circuit currents close to 8 mA?cm-2, and power conversion efficiencies over 3%.
- Haid, Stefan,Mishra, Amaresh,Uhrich, Christian,Pfeiffer, Martin,Baeuerle, Peter
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experimental part
p. 4435 - 4444
(2012/05/05)
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