- High-Efficiency Cycloruthenated Sensitizers for Dye-Sensitized Solar Cells
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Four thiocyanate-free ruthenium sensitizers (DUY24-DUY27) containing 2-thienylpyridine moiety as cyclometalating core were synthesized for dye-sensitized solar cell (DSC) application. To the best of our knowledge, DUY24-DUY27 are four best-efficiency sens
- Nguyen, The-Duy,Lan, Yen-Po,Wu, Chun-Guey
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- Orthogonal functionalization of cyclopenta[hi]aceanthrylenes
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A synthetic strategy to prepare 2,7- or 4,9-functionalized cyclopenta[hi]aceanthrylenes that are capable of Suzuki cross-coupling reactions is demonstrated. This method has been utilized to create a series of thiophene derivatized compounds that were subsequently used to investigate the role of substitution pattern on the photophysical and electronic properties of cyclopenta[hi]aceanthrylenes. The orthogonal functionalization provides access to unique substitution patterns (e.g., cruciform-like architectures) and materials with small optical band gaps (1.22-1.97 eV).
- Lee, Che-Hsiung,Plunkett, Kyle N.
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- Synthesis and photovoltaic properties of a star-shaped molecule based on a triphenylamine core and branched terthiophene end groups
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A new star-shaped donor-acceptor molecule has been synthesized for application as the donor material in solution-processed bulk-heterojunction organic solar cells (OSCs). The molecule consists of a triphenylamine (TPA) unit as the core and a donor unit with three arms containing benzo[1,2,5]thiadiazole (BT) acceptor units and 5,5″-dihexyl-2,2′:3′,2″- terthiophene (tTh) end groups. The molecule, denoted S(TPA-BT-tTh), exhibits a broad absorption band in the wavelength range 300-650 nm and high hole mobility of 1.1×10-4 cm2 V-1 s-1. An OSC device based on S(TPA-BT-tTh) as donor and [6,6]-phenyl C 71-butyric acid methyl ester (PC70BM) as the acceptor (1:3, w/w) exhibited a power conversion efficiency of 2.28% with a short circuit current density of 6.39 mA/cm2 under illumination of AM.1.5, 100 mW/cm2.
- Gao, Lei,Zhang, Jing,He, Chang,Shen, Suling,Zhang, Yi,Liu, Hongtao,Sun, Qingjiang,Li, Yongfang
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- The function of Chalcogenophene in the Cyclomatelated Ring of the Cycloruthenated Dyes applied in Dye-Sensitized Solar Cell
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Three thiocyanate-free cycloruthenated complexes, DUY24-O, DUY24, and DUY24-Se containing furan, thiophene, and selenophene, respectively, as a part of the cycloruthenated ring, were designed to reveal the function of the chalcogen atom on the physicochemical and photovoltaic performance of the cycloruthenated sensitizers applied in dye-sensitized solar cells (DSCs). The three sensitizers have a similar molecular size; therefore, the effect of molecular dimensions on their photovoltaic performance can be negligible. NMR data, electron-donating resonance effects, optical properties, and the energy levels of the frontier orbitals reveal that the physical/photovoltaic properties of the three sensitizers were affected significantly by the chalcogen atom on the cyclometalated chalcogenophene ring. The λmax (both in ethanol and adsorbed on TiO2), frontier orbital level, and dye loading of thiophene- and selenophene-containing dyes are very close. Nevertheless, DUY24-Se has a higher molar absorption coefficient compared to DUY24; therefore, the DSC based on DUY24-Se has higher efficiency (8.4% under AM1.5 G one-sun and 26% under T5-light at ca. 6000 lux) than that sensitized with the DUY24 dye. These efficiencies are also higher than those (7.9 and 21.6%, respectively) of the cell dyed with N719, fabricated using the same conditions. The better performance of the device sensitized with DUY24-Se compared to DUY24-based cells suggests that selenophene is as good as (or even better than) thiophene to be a part of the cyclometalated ring for thiocyanate-free cycloruthenated sensitizers applied in DSCs. Furan-containing DUY24-O has much worse photovoltaic performance compared to the other two dyes. This is not only because DUY24-O has the shortest λmax, the lowest molar absorption coefficient, and the highest HOMO level but also the lowest dye loading (because of the strong interaction between the oxygen in furan and TiO2, the array of DUY24-O occupies more surface when adsorbed on TiO2) and the fastest charge recombination. The physicochemical and photovoltaic properties as well as the adsorption behavior of the dye on the TiO2 anode for the cycloruthenated sensitizers affected significantly by the chalcogen atom of the chalcogenophene on the cyclometalated ring provide a new strategy to design high-efficiency NCS-free cyclometalated sensitizers for DSCs.
- Nguyen, The-Duy,Lan, Yen-Po,Wu, Chun-Guey
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- A First Synthesis of Thiophene Dendrimers
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(Matrix Presented) Thiophene dendrons and dendrimers were designed and synthesized using a convergent approach. Metal-mediated coupling reactions were used in the synthesis. A rational approach allowed the formation of αα, ββ, and αβ linkages between the dendrons and thiophene units.
- Xia, Chuanjun,Fan, Xiaowu,Locklin, Jason,Advincula, Rigoberto C.
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- Efficient synthesis of carbazolyl- and thienyl-substituted β-diketonates and properties of their red- and green-light-emitting Ir(III) complexes
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The efficient synthesis of novel β-diketonates equipped with functional carbazolyl moieties and their subsequent transformations in 5-hexyl-thienyl substituted carbazole derivatives is presented by utilizing an effective Stille cross-coupling reaction. Th
- Tian, Nan,Thiessen, Alexander,Schiewek, Ralf,Schmitz, Oliver J.,Hertel, Dirk,Meerholz, Klaus,Holder, Elisabeth
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- Synthesis and enhanced electron transfer of supramolecular nano-composite containing dendritic dye and surface-modified ZnO nano-rods
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Supramolecular nano-composites 15T5N/ZnOx-PNH containing enhanced compatibilities of dendritic dye 15T5N and surface-modified nano-rod ZnOx-PNH were developed in this study. The physical properties of supramolecular nano-composites have been well investigated by theoretical calculation and various measurements, including UV–visible, PL, TEM, TCSPC, FT-IR, and CV. H-bonded nano-composite 15T5N/ZnO30-PNH possessed the saturated quenched fluorscence as dendritic dye 15T5N complexed with surface-modified nano-rod ZnO30-PNH. In contrast to nano-rod mixture 15T5N/ZnO (without surface-modification), more widened visible absorption band to promote more efficient photo-induced charge separation phenomenon was observed in supramolecular nano-composite 15T5N/ZnO30-PNH. Compared with surfactant T-PNH, less efficient electron transfer of surfactant T-PC6 was observed in TCSPC and PL measurements because of the steric hindrance of long alkyl chains (-C6H13) attached to surfactant T-PC6. Therefore, the triple H-bonds between dendritic dye 15T5N and surface-modified nano-rod ZnO30-PNH are verified to result in the desirable effective electron transfer in supramolecular nano-composite 15T5N/ZnO30-PNH.
- Lin, Chien-Min,Li, Ming-Shiou,Dwivedi, Atul Kumar,Lin, Hong-Cheu
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- Optical ON/OFF switching of intramolecular photoinduced charge separation in a donor-bridge-acceptor system containing dithienylethene
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In the newly designed photoswitchable electron transfer compound 2, our previously published donor-bridge-acceptor system (anthracene-CH2- bithiophene-pyridinium) is modified by incorporation of the photoisomerizable dithienylethene (DTE) as a switching unit. In the open-ring form 2a, excitation of the anthracene donor leads to an intramolecular charge separation proved by identification of the anthracene radical cation in transient absorption spectra (ON state). After photocyclization to the closed-ring isomer (2a → 2b), the intramolecular charge separation is completely suppressed (OFF state). The reversibility of the ON/OFF switching is verified. From UV-vis absorption spectra and cyclovoltammetric studies it is deduced that in the open-ring isomer 2a (ON state) conjugation is markedly restricted within the dithienylethene bridge, whereas in the closed-ring isomer 2b (OFF state) the conjugation is extended over the whole dithienylethenepyridinium (DTEP) subunit. Consequently, in 2 an enlarged conjugation within the bridge is not decisive for photoinduced charge separation. Instead the observed transfer properties can be understood by thermodynamic aspects.
- Endtner, Jochen M.,Effenberger, Franz,Hartschuh, Achim,Port, Helmut
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- Facile synthesis and characterization of a novel thiophene-fused polycyclic aromatics based on pyrene
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A novel large thiophene-fused polycyclic aromatics 1 based on pyrene 5 has been synthesized, and its structure was confirmed by 1H NMR, 13C NMR, MS, UV-vis and elemental analysis. The key steps of the synthesis involved the Stille cross-coupling reaction and followed by selective β-β oxidative cyclization of pendant thienyl rings by FeCl3 under mild conditions.
- Duan, Zong Fan,Yang, Zhi Gang,Liu, Dong Jie,Cai, Li,Hoshino, Daiki,Morita, Tsuyoshi,Zhao, Gao Yang,Nishioka, Yasushiro
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- Spiro[fluorene-9,9'-xanthene]-based small organic molecule hole transport material as well as preparation method and application thereof
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The invention discloses an organic small molecule hole transport material based on spiro[fluorene-9,9'-xanthene]-based and a preparation method and application thereof, and the organic small moleculehole transport material takes spiro[fluorene-9,9'-xanthene] as a core, and has good amorphous form and excellent dissolving property; besides, different numbers of thiophene groups are added into sidechains, so that the material is endowed with more excellent physical and photoelectric properties through the characteristics of high electron density, excellent carrier transport capacity, controllable optical and electrochemical properties and the like; in addition, due to modification of a terminal alkyl chain, the dissolvability is improved, the film-forming property of the material is facilitated, and the material is easier to process; meanwhile, the synthesis is simple, raw materials are easy to obtain, and cost is low. The organic small molecule hole transport material is applied to anall-inorganic perovskite solar cell, and the cell efficiency of the organic small molecule hole transport material is higher than the original cell efficiency, which shows that the organic small molecule hole transport material has practical significance for improving the efficiency of the all-inorganic perovskite solar cell.
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Paragraph 0025-0027; 0031-0033
(2021/01/29)
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- Cata-Condensed Heteroannulated Coronenes via Selective Bromination of Diarenoperylenes as the Key Step
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A facile three-step synthetic route to heteroannulated extended coronenes via a selective bromination of diarenoperylenes as the key step is presented. The heteroannulated coronenes were characterized by X-ray crystallography and by photophysical and electrochemical means.
- Yang, Xuan,Rominger, Frank,Mastalerz, Michael
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supporting information
p. 7270 - 7273
(2018/11/23)
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- Effect of conjugated side groups on the photovoltaic performances of triphenylamine-based dyes sensitized solar cells
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Three novel organic dyes (LD1, LD2 and LD3) with conjugated side groups on the thiophene π-bridge are designed and synthesized for dye sensitized solar cells (DSSCs). The photophysical, electrochemical, and photovoltaic properties of the dyes have been successfully tuned by incorporating different conjugated side groups into the thiophene π-bridges moieties of dyes. Compared with the analogous dyes with non-conjugated side groups, the side group-conjugated dyes exhibited wider absorption spectra, higher molar extinction coefficients, and better photovoltaic performances. For the LD2-based DSSCs, the maximum power conversion efficiency (PCE) of 7.71% is obtained under AM 1.5 G irradiation (100 mW cm-2). The result demonstrates that high-performance DSSCs can be acquired by choosing suitable conjugated side groups into the π-bridges moieties of organic dyes.
- Long, Jun,Liu, Xunshan,Guo, Huan,Zhao, Bin,Tan, Songting
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p. 222 - 231
(2015/10/19)
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- Ligand Engineering for the Efficient Dye-Sensitized Solar Cells with Ruthenium Sensitizers and Cobalt Electrolytes
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Over the past 20 years, ruthenium(II)-based dyes have played a pivotal role in turning dye-sensitized solar cells (DSCs) into a mature technology for the third generation of photovoltaics. However, the classic I3-/I- redox couple limits the performance and application of this technique. Simply replacing the iodine-based redox couple by new types like cobalt(3+/2+) complexes was not successful because of the poor compatibility between the ruthenium(II) sensitizer and the cobalt redox species. To address this problem and achieve higher power conversion efficiencies (PCEs), we introduce here six new cyclometalated ruthenium(II)-based dyes developed through ligand engineering. We tested DSCs employing these ruthenium(II) complexes and achieved PCEs of up to 9.4% using cobalt(3+/2+)-based electrolytes, which is the record efficiency to date featuring a ruthenium-based dye. In view of the complicated liquid DSC system, the disagreement found between different characterizations enlightens us about the importance of the sensitizer loading on TiO2, which is a subtle but equally important factor in the electronic properties of the sensitizers.
- Aghazada, Sadig,Gao, Peng,Yella, Aswani,Marotta, Gabriele,Moehl, Thomas,Teuscher, Jo?l,Moser, Jacques-E.,De Angelis, Filippo,Gr?tzel, Michael,Nazeeruddin, Mohammad Khaja
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supporting information
p. 6653 - 6659
(2016/07/19)
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- Structural design of benzo[1,2- b:4,5- b ′]dithiophene-based 2D conjugated polymers with bithienyl and terthienyl substituents toward photovoltaic applications
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In this contribution, six conjugated polymers consisting of benzo[1,2-b:4,5-b′]dithiophene-bithiophene (BDT-BT) and benzo[1,2-b:4,5-b′]dithiophene-benzothiadiazle (BDT-BTD) as building blocks in the main chain were synthesized by coupling polymerization and utilized for photovoltaic applications. By directly attaching three kinds of alkylthienyl side chains to the conjugated main chain, the resulted two-dimensional configuration revealed a broader absorption range due to the ground state electron transition of their corresponding alkylthienyl units and polymer backbone. Temperature-dependent absorbance, emission spectra, and thermal annealing further verify that the shoulder band(s) were originated from the aggregated (crystalline) species of polymers. The photovoltaic properties of the donor-acceptor polymers revealed well-defined side chain geometries, physical, and electronic structures and showed the highest power conversion efficiency of 4.25% among polymer solar cells based on two-dimensional (2-D) bithienyl- or terthienyl-substituted benzodithiophene.
- Kuo, Cheng-Yu,Nie, Wanyi,Tsai, Hsinhan,Yen, Hung-Ju,Mohite, Adytia D.,Gupta, Gautam,Dattelbaum, Andrew M.,William, Darrick J.,Cha, Kitty C.,Yang, Yang,Wang, Leeyih,Wang, Hsing-Lin
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p. 1008 - 1020
(2014/03/21)
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- Small asymmetric anthracene-thiophene compounds as organic thin-film transistors
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Anthracene and thiophene compounds are promising materials for OTFTs. We report here, the synthesis, as well as the physical, thermal, and optoelectronic properties of alkyl-substituted asymmetric anthracene-thiophene compounds connected by a bridged triple bond. The target molecules were synthesized using 2-bromoanthracene as the starting material, and the proceeding reactions included alkylation, bromination, and the Sonogashira coupling reaction. The synthesized compounds were both thermally and electrochemically stable. Among the synthesized compounds, HTEA (7a) and DTEA (7b) showed mobility and on/off ratio values of 1.3×10-1 cm2/V s, 2.6×10 6 and 2.0×10-2 cm2/V s, 1.0×10 6, respectively.
- Shaik, Baji,Park, Ji Hee,An, Tae Kyu,Noh, Young Ri,Yoon, Soon Byung,Park, Chan Eon,Yoon, Young Jin,Kim, Yun-Hi,Lee, Sang-Gyeong
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p. 8191 - 8198
(2013/09/02)
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- Effect of side-chain architecture on the optical and crystalline properties of two-dimensional polythiophenes
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The present study reported here synthesis of three novel two-dimensional (2D) polythiophene derivatives with conjugated terthiophene-vinylene side chain - poly{3-(5″-hexyl-2,2′:5′,2″-terthiophenyl-5-vinyl) thiophene-alt-thiophene} (P1), poly{3-(5,5″-dihexyl-2,2′:5′, 2″-terthiophenyl-3′-vinyl)thiophene-alt-thiophene} (P2), and poly{3-(4,4″-dihexyl-2,2:5′,2″-terthiophene-3′-vinyl) thiophene-alt-thiophene} (P3) - that were synthesized via stille coupling reaction. The terthiophene side chain with different conformations conjugated to the polythiophene main chain via vinyl linkage provided the ability to control the molecular organization, hence affecting the optoelectronic and electrochemical properties of 2D polymers. TD-DFT calculation with the B3LYP/6-31+g(d) function on electronic structures of the monomers was consistent with the experimental results. It suggested that the energetic states of HOMO and LUMO were highly dependent on the side-chain architectures. These polythiophene thin films fabricated by spin-casting show a broader absorption ranges from 300 to 700 nm which was significantly wider than the absorption of pure poly(3-hexylthiophene). When comparing the solid-state absorption spectra of these polymers before and after thermal annealing, P3 displayed the most red-shift in the wavelength range between 450 and 700 nm. It was presumably due to an extended conjugation length resulting from the linear conformation and preferred chain packing, as manifested in the X-ray diffraction. Molecular dynamics (MD) simulation on polymers with different side chains in isolated and packed states suggests planar conformation of the main chain was adopted and regulated by the side chains which were placed in parallel with the main-chain direction. Interestingly, P1 solution revealed an excitation-dependent emission property, suggesting a structural inhomogeneity in solution. Contrary to P1, the PL spectra of P2 and P3 showed only one emission peak at 460 nm, regardless of the excitation energy. Orientation and regiochemistry of the terthiophene side chain had a major impact on the overall optical and electronic properties of the polymer. Moreover, the HOMO and LUMO of these three polymers had been determined through cyclic voltammetry. HOMO of the three polymers were in the following order: P1 > P2 > P3. It implied that the energy level was regiochemistry dependent and directly associated with the linked position between backbone and conjugated side chain. Most importantly, through mesogen-jacketed-like design strategy employed in the present study, the improved packing of these two-dimensional polymers offered insights into structure design to enhance properties that have strong ties to the electronic devices.
- Kuo, Cheng-Yu,Huang, Yu-Chen,Hsiow, Chuen-Yo,Yang, Yu-Wen,Huang, Ching-I,Rwei, Syang-Peng,Wang, Hsing-Lin,Wang, Leeyih
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p. 5985 - 5997
(2013/09/02)
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- A first synthesis and physical properties of asymmetric anthracenes-thiophenes bridged with ethylene
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Here we report our recent result of a new semiconductor material, which has an asymmetric structure. The synthesized molecules consist of anthracene and thiophene connected by bridged ethylene and substituted with hexyl or dodecyl groups as pendants. The semiconductors were synthesized using a McMurry coupling reaction between anthracene-2-carbaldehyde and corresponding 5-hexyl(or dodecyl)thiophene-2-carbaldehyde. A first investigation of synthesized asymmetry AVHT (9a) and AVDT (9b) for the physical properties showed that they have high oxidation potential and thermal stability. The devices prepared by using AVHT (9a) and AVDT (9b) showed the mobility of 2.6 × 10-2 cm 2/Vs and 4.4 × 10-3 cm2/Vs, respectively, in solution processed OTFTs.
- Hwang, Min Ji,Park, Ji Hee,Jeong, Eun Bin,Kang, Il,Lee, Dong Hoon,Park, Chan Eon,Singh,Choi, Ho June,Kim, Yoon-Hi,Yoon, Yong Jin,Kwon, Soon-Ki,Lee, Sang-Gyeong
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p. 3810 - 3816
(2013/01/16)
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- Synthesis, electronic, and morphological properties of tetrahedral oligothiophenes with n-hexyl terminal groups
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A series of tetrahedral oligothiophenes bearing n-hexyl groups at the α-positions of the terminal thiophene rings, (n-C6H 13(C4H2S)n)4C (Hex-TnTM; n=1-4), has been synthesized by Kosugi-Migita-Stille coupling as a key reaction. Thanks to the improved solubility afforded by the terminal n-hexyl groups, the largest homologue (n=4) was successfully obtained. Whereas the smaller derivatives (n=1, 2) were obtained as liquid substances, the larger derivatives (n=3, 4) were obtained as solids. Hex-T3 TM partially adopts syn conformations between the adjacent thiophene rings in the crystal, probably owing to the packing force. Hex-T3 TM not only appeared in the crystalline state but also the amorphous state, which was stable to up to 80 °C. Regardless of the terminal groups, the derivatives of n=2 exhibited a broad fluorescence with large Stokes shifts compared to the corresponding linear analogues, thereby suggesting the presence of intramolecular interactions between the bithiophene moieties. Interactions between terthiophene branches was also suggested in the radical cations of Hex-T3 TM by cyclic voltammetry measurements.
- Matsumoto, Kouzou,Kugo, Sota,Takajo, Daisuke,Inaba, Akira,Hirao, Yasukazu,Kurata, Hiroyuki,Kawase, Takeshi,Kubo, Takashi
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supporting information; experimental part
p. 225 - 232
(2012/04/04)
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- ORGANIC METAL DYE, AND PHOTOELECTRIC ELEMENT AND DYE-SENSITIZED SOLAR CELL USING THE ORGANIC METAL DYE
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The present invention relates to an organic metal dye comprising fused heterocyclic derivatives, and to a photoelectric element and to a dye-sensitized solar cell using the organic metal dye.
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Page/Page column 37
(2012/10/08)
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- Synthesis and mesophase behavior of phenylthiophene based amphiphilic molecules
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Novel amphiphilic molecules consisting of a rigid 2-phenylthiophene core, with a polar flexible tri(oxylethylene) moiety attached to the phenyl ring and one or two alkyl chains attached to the thiophene ring at the other side have been synthesized by using Ni(II) and Pd(0) catalyzed coupling reaction as key steps. The tri(oxylethylene) moieties were terminated with hydroxyl group, sodium carboxylate group and lithium carboxylate group respectively. The thermotropic and solvent induced liquid crystalline behavior of these substances was investigated by polarized optical microscopy, differential scanning calorimetry and X-ray diffraction. Thereby the influence of the terminal groups attached to the tri(oxylethylene) moities as well as the influence of the length and the number of the alkyl chains on the mesophase behavior were investigated. The single alkyl chain Na-carboxylate termianted derivatives show smectic A phases, double alkyl chain Na-carboxylate terminated derivatives show a thermo tropic hexagonal columnar mesophase, while columnar mesophases are found in both single and double alkyl chain Li-carbonate terminated derivatives. The model for molecular organization in the hexagonal columnar mesophase is established.
- Jing, Shan,Zhang, Ruilin,Dai, Heng,Du, Chao,Cheng, Xiaohong
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scheme or table
p. 577 - 584
(2012/06/04)
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- Optical properties of oligothiophene substituted diketopyrrolopyrrole derivatives in the solid phase: Joint J- and H-type aggregation
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Photophysical properties of diketopyrrolopyrrole derivatives substituted with oligothiophenes are investigated. All compounds are found to be fluorescent both in solution and in the solid phase. At low temperature in the solid, fluorescence originates from excimer-like excited states. Comparison of absorption and fluorescence excitation spectra taken under matrix isolated conditions and on solid films show the presence of both J- and H-type absorption bands in the solid phase. Quantum-chemical calculations, including exciton-phonon coupling to account for deviations from the Born-Oppenheimer approximation, are performed to simulate the band shape of the lowest absorption band in the molecular solid. The joint presence of J- and H-bands is explained by the presence of two molecules in the unit cell. The Davydov splitting is substantial for molecules with linear alkyl substituents on the nitrogen atom (on the order of 0.2 eV) but can be reduced to almost zero by introducing branching at the β-carbon of the alkyl side chain.
- Kirkus, Mindaugas,Wang, Linjun,Mothy, Sebastien,Beljonne, David,Cornil, Jerome,Janssen, Rene A. J.,Meskers, Stefan C. J.
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scheme or table
p. 7927 - 7936
(2012/09/21)
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- High-performance solution-processed solar cells and ambipolar behavior in organic field-effect transistors with thienyl-BODIPY scaffoldings
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Green-absorbing dipyrromethene dyes engineered from bis-vinyl-thienyl modules are planar molecules, exhibiting strong absorption in the 713-724 nm range and displaying comparable electron and hole mobilities in thin films (maximum value 1 × 10-3 cm2/(Vs)). Bulk heterojunction solar cells assembled with these dyes and a fullerene derivative (PC61BM) at a low ratio give a power conversion efficiency as high as 4.7%, with short-circuit current values of 14.2 mA/cm2, open-circuit voltage of 0.7 V, and a broad external quantum efficiency ranging from 350 to 920 nm with a maximum value of 60%.
- Bura, Thomas,Leclerc, Nicolas,Fall, Sadiara,Lévêque, Patrick,Heiser, Thomas,Retailleau, Pascal,Rihn, Sandra,Mirloup, Antoine,Ziessel, Raymond
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supporting information
p. 17404 - 17407
(2013/01/15)
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- Efficient charge generation and collection in organic solar cells based on low band gap dyad molecules
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Low band gap dyad molecules were prepared that have absorption spectra matched well with the solar spectrum, and the construction of efficient charge transport pathways was observed. Under AM 1.5 illumination, the devices have achieved the highest JSC (4.79 mA cm2) and FF (0.46) in dyad-based organic solar cells to date.
- Izawa, Seiichiro,Hashimoto, Kazuhito,Tajima, Keisuke
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supporting information; experimental part
p. 6365 - 6367
(2011/07/08)
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- Star-shaped oligothiophene-arylene derivatives and organic thin film transistors using the same
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A star-shaped oligothiophene-arylene derivative in which an oligothiophene having p-type semiconductor characteristics is bonded to an arylene having n-type semiconductor characteristics positioned in the central moiety of the molecule and forms a star shape with the arylene, thereby simultaneously exhibiting both p-type and n-type semiconductor characteristics. Further, an organic thin film transistor using the oligothiophene-arylene derivative. The star-shaped oligothiophene-arylene derivative can be spin-coated at room temperature, leading to the fabrication of organic thin film transistors simultaneously satisfying the requirements of high charge carrier mobility and low off-state leakage current.
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Page/Page column 17-18
(2010/04/25)
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- HIGH PERFORMANCE SOLUTION PROCESSABLE SEMINCONDUCTOR BASED ON DITHIENO [2,3-D:2',3'-D']BENZO[1,2-B:4,5-B'] DITHIOPHENE
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Dithienobenzodithiophenes of general formula (I) in which R1 to R6 are each independently selected from a) H, b) halogen, c) -CN, d) -NO2, e) - OH, f) a C1-20 alkyl group, g) a C2-20 alkenyl group, h) a C2-20 alkynyl group, i) a C1-20 alkoxy group, j) a C1-20 alkylthio group, k) a C1-20 haloalkyl group, I) a -Y- C3-10 cycloalkyl group, m) a -Y-C6-14 aryl group, n) a -Y-3-12 membered cyclo- heteroalkyl group, or o) a -Y-5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the 3-12 membered cyc- loheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1 -4 R7 groups, wherein R1 and R3 and R2 and R4 may also together form an aliphatic cyclic moiety, Y is independently selected from divalent a C1-6 alkyl group, a divalent C1-6 haloalkyl group, or a covalent bond; and m is independently selected from 0, 1, or 2. The invention also relates to the use of the dithienobenzodithiophenes according to any of claims 1 to 4 as semiconductors or charge transport materials, as thin-film transistors (TFTs), or in semiconductor components for organic light-emitting diodes (OLEDs), for photovoltaic components or in sensors, as an electrode material in batteries, as optical waveguides or for electrophotography applications.
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Page/Page column 17-18
(2010/04/03)
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- PERYLENE TETRACARBOXIMIDE DERIVATIVES FOR PHOTOVOLTAIC DEVICES
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The compounds of the present invention are represented by the following formula (I): wherein M is represented by the following formula: with R1, R2, R3, R4, R5, R6, R7, R8, R10, R11, X1, X2, X3, L, a, b, c, d, e, x, y, and z defined herein.
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Page/Page column 17
(2010/04/03)
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- End-capping of conjugated thiophene-benzene aromatic systems
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The synthesis of end-capped thieno[3,2-f:4,5-f′]bis[1]benzothiophene was achieved from thiophene and 2,5-thiophenedicarboxaldehyde. Specifically, hexyl and dodecyl end-capping groups conferred reversible redox behavior as evidenced by cyclic voltammetry with oxidation potentials of 0.73 V versus Fc/Fc+ couple. An extensive spectrophotometric analysis is reported.
- Wex, Brigitte,Jradi, Fadi M.,Patra, Digambara,Kaafarani, Bilal R.
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scheme or table
p. 8778 - 8784
(2010/12/25)
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- NOVEL PORPHYRAZINE DERIVATIVE AND INTERMEDIATE THEREOF, METHOD FOR PRODUCTION OF NOVEL PORPHYRAZINE DERIVATIVE AND INTERMEDIATE THEREOF, AND USE OF PORPHYRAZINE DERIVATIVE
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A porphyrazine derivative in which porphyrazine forms a condensed ring with thiophene and a skeleton of the thiophene has a functional group such as an alkyl group at position 2 has a high solubility in an organic solvent and exhibits a high crystallinity. Therefore, the porphyrazine derivative is suitably used in crystalline thin-film formation using a solution process. This provides a novel porphyrazine derivative and an intermediate thereof, which porphyrazine derivative has a high solubility in an organic solvent and is excellent in molecular orientation, a method for production of the porphyrazine derivative and the intermediate, and use of the porphyrazine derivative and the intermediate.
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Page/Page column 17; 33
(2010/01/07)
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- Enhance the optical absorptivity of nanocrystalline TiO2 film with high molar extinction coefficient ruthenium sensitizers for high performance dye-sensitized solar cells
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We report two new heteroleptic polypyridyl ruthenium complexes, coded C101 and C102, with high molar extinction coefficients by extending the π-conjugation of spectator ligands, with a motivation to enhance the optical absorptivity of mesoporous titania film and charge collection yield in a dye-sensitized solar cell. On the basis of this C101 sensitizer, several DSC benchmarks measured under the air mass 1.5 global sunlight have been reached. Along with an acetonitrile-based electrolyte, the C101 sensitizer has already achieved a strikingly high efficiency of 11.0-11.3%, even under a preliminary testing. More importantly, based on a low volatility 3-methoxypropionitrile electrolyte and a solvent-free ionic liquid electrolyte, cells have corresponding >9.0% and ～7.4% efficiencies retained over 95% of their initial performances after 1000 h full sunlight soaking at 60°C. With the aid of electrical impedance measurements, we further disclose that, compared to the cell with an acetonitrile-based electrolyte, a dye-sensitized solar cell with an ionic liquid electrolyte shows a feature of much shorter effective electron diffusion lengths due to the lower electron diffusion coefficients and shorter electron lifetimes in the mesoporous titania film, explaining the photocurrent difference between these two type devices. This highlights the next necessary efforts to further improve the efficiency of cells with ionic liquid electrolytes, facilitating the large-scale production and application of flexible thin film mesoscopic solar cells.
- Gao, Feifei,Wang, Yuan,Shi, Dong,Zhang, Jing,Wang, Mingkui,Jing, Xiaoyan,Humphry-Baker, Robin,Wang, Peng,Zakeeruddin, Shaik M.,Graetzel, Michael
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experimental part
p. 10720 - 10728
(2009/02/05)
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- Synthesis and the effect of alkyl chain length on optoelectronic properties of diarylethene derivatives
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Photochromic symmetrical diarylethene derivatives 1a-6a bearing different long alkyl chains at 2-position of thiophene rings have been synthesized and their structures have been determined by single-crystal X-ray diffraction analysis. The effect of alkyl chain length on their optoelectronic properties, such as photochromism in solution as well as in the crystalline phase and electrochemical performance was investigated in detail. These diarylethenes have showed good photochromic behavior both in solution and in the single crystalline phase. Introduction of the long alkyl chains at 2-position of bis(5-formyl-3-thienyl)perfluorocyclopentene increased the absorption coefficients of both open- and closed-ring isomers and induced bathochromic shifts of the maximal wavelength absorption of the closed-ring isomers. The long alkyl chains can also decrease the cyclization/cycloreversion quantum yields and the oxidation potentials. The cyclic voltammetry indicated that the band gap of these diarylethene derivatives was significantly affected by the alkyl chain length.
- Zheng, Chunhong,Pu, Shouzhi,Xu, Jingkun,Luo, Mingbiao,Huang, Dechao,Shen, Liang
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p. 5437 - 5449
(2008/01/07)
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- Synthesis of end-blocked thienyl oligomers incorporating benzo[c]thiophene
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A straightforward synthesis of end-capped bithienyl, quaterthienyl and sexithienyl systems incorporating benzo[c]thiophene units is presented.
- Mohanakrishnan, Arasambattu K.,Amaladass,Arul Clement
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p. 779 - 784
(2007/10/03)
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- Dibenzothiophene derivatives as new prototype semiconductors for organic field-effect transistors
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New prototype semiconductor materials based on dibenzothiophene (DBT) derivatives were successfully synthesized by a convergent approach using palladium catalyzed Stille coupling reactions. Thermogravimetric analysis, UV-vis spectra and electrochemistry results indicated these materials had good thermal and photooxidation stability. X-Ray diffraction measurements of the vacuum-evaporated films showed enhanced crystalline order with increasing substrate deposition temperature. The ordered vacuum-evaporated films with charge carrier mobility as high as 7.7 × 10-2 cm2 V-1 s-1 and an on/off ratio of nearly 1 × 10 7 had been achieved with 3,7-bis(5′-hexyl-thiophen-2′-yl) -dibenzothiophene (3,7-DHTDBTT). These results suggest that the 3,7-substituted DBT system is a good prototype for new type organic semiconductors and will play a more important role in organic semiconductors. The Royal Society of Chemistry.
- Gao, Jianhua,Li, Liqiang,Meng, Qing,Li, Rongjin,Jiang, Hui,Li, Hongxiang,Hu, Wenping
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p. 1421 - 1426
(2008/02/07)
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- Large area liquid crystal monodomain field-effect transistors
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Butyl, hexyl, and decyl derivatives of the liquid-crystalline organic semiconductor 5,5″-bis(5-alkyl-2-thienylethynyl)-2,2′:5′, 2″-terthiophene were synthesized and studied with respect to their structural, optical, and electrical properties. By means of an optimized thermal annealing scheme the hexyl and decyl compounds could be processed into self-assembled monodomain films of up to 150 mm in diameter. These were investigated with X-ray diffractometry, which revealed a clearly single-crystalline monoclinic morphology with lamellae parallel to the substrate. Within the lamellae the molecules were found to arrange with a tilt of about 50° with the rubbing direction of the polyimide alignment layer. The resulting, close side-to-side packing was confirmed by measurements of the UV/vis absorption, which showed a dichroic ratio of 19 and indicated H-aggregation. AFM analyses revealed self-affinity in the surface roughness of the monodomain. The compounds showed bipolar charge transport in TOF measurements, with hole mobilities reaching up to 0.02 cm2/Vs and maximum electron mobilities around 0.002 cm2/Vs. The hexyl derivative was processed into large-area monodomain top-gate field-effect transistors, which were stable for months and showed anisotropic hole mobilities of up to 0.02 cm2/Vs. Compared to multidomain bottom-gate transistors the monodomain formation allowed for a mobility increase by 1 order of magnitude.
- Van Breemen, Albert J. J. M.,Herwig, Peter T.,Chlon, Ceciel H. T.,Sweelssen, Joergen,Schoo, Herman F. M.,Setayesh, Sepas,Hardeman, Willie M.,Martin, Christian A.,De Leeuw, Dago M.,Valeton, Josue J. P.,Bastiaansen, Cees W. M.,Broer, Dirk J.,Popa-Merticaru, Andreea R.,Meskers, Stefan C. J.
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p. 2336 - 2345
(2007/10/03)
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- Luminescent organoboron quinolate polymers
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The synthesis of well-defined luminescent organoboron polymers via a novel three-step procedure starting from silylated polystyrene is reported. Highly selective borylation of poly(4-trimethylsilylstyrene) (PS-Si), followed by replacement of the bromine substituents in poly(4-dibromoborylstyrene) (PS-BBr) with substituted thienyl groups (R = H, 3-hexyl, 5-hexyl), and final introduction of the 8-hydroxyquinolato moiety yields a series of new organoboron quinolate polymers in 67-83% isolated yield. The hexyl-substituted polymers are highly soluble and solution-processable yielding thin films that efficiently emit light at 513-514 nm upon excitation at 395 nm.
- Qin, Yang,Pagba, Cynthia,Piotrowiak, Piotr,Jaekle, Frieder
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p. 7015 - 7018
(2007/10/03)
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- Mesomorphic compound, liquid crystal composition, liquid crystal device, display apparatus and display method
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A mesomorphic compound represented by the following formula (I): STR1 wherein R1 and R2 respectively denote a linear or branched alkyl group having 1-18 carbon atoms capable of including one or two or more non-neighboring methylene groups which can be replaced with STR2 wherein X denotes halogen; X1 and X2 respectively denote STR3 Z1 denotes STR4 A1 denotes a single bond, STR5 and Y1 and Y2 respectively denote H, F, Cl, Br, --CH3 or --CF3 with the proviso that Y1 and Y2 are not simultaneously H. The mesomorphic compound is effective for providing a ferroelectric liquid crystal composition showing an improved low-temperature operation characteristic and a decreased temperature-dependence of response speed.
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- Mesomorphic compound, liquid crystal composition containing same and liquid crystal device using same
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A mesomorphic compound represented by the following formula (I): STR1 wherein R1 and R2 respectively denote a linear or branched alkyl group having 1-18 carbon atoms capable of having a substituent; X1 denotes any one of a single bond, --O--, STR2 X2 denotes any one of a single bond, --O--, STR3 Z1 denotes any one of STR4 --CH2 O-- and --CH=C(CN)--; and A1 denotes --A2 -- or --A2 --A3 -- wherein A2 and A3 respectively denote any one of STR5
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- Mesomorphic compound, liquid crystal composition and liquid crystal device using same
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A mesomorphic compound represented by the following formula (I): STR1 wherein R1 and R2 respectively denote a linear or branched alkyl group having 1-18 carbon atoms capable of having a substituent; X denotes any one of a single bond, --O--, STR2 Y denotes STR3 or --CH2 O--; and Z denotes any one of --O--, STR4 .
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