- Conjugated polymers based on dicarboxylic imide-substituted isothianaphthene and their applications in solar cells
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Four new polymers containing a benzo[c]thiophene-N-dodecyl-4,5-dicarboxylic imide (DIITN) unit including the homopolymer and three donor-acceptor copolymers were designed, synthesized, and characterized. For these copolymers, DIITN unit with low bandgap was selected as an electron acceptor, whereas 5,5′-(2,7-bisthiophen-2-yl)-9-(2-decyltetradecyl)-9H-carbazole), 5,5′-(3,3′-di-n-octylsilylene-2,2′-bithiophene), and 5,5′-(2,7-bisthiophen-2-yl-9,9-bisoctyl-9H-fluoren-7-yl) were chosen as the electron donor units to tune the highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO/LUMO) levels of the copolymers for better light harvesting. These polymers exhibit extended absorption in the visible and near-infrared range and are soluble in common organic solvents. The relative low lying HOMO of these polymers promises good air stability and high open-circuit voltage (Voc) for photovoltaic application. Bulk heterojunction solar cells were fabricated by blending the copolymers with [6,6]-phenyl-C61-butyric acid methyl ester or [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). The best power conversion efficiency of 1.6% was achieved under simulated sunlight AM 1.5G (100 mW/cm2) from solar cells containing 20 wt % of the fluorene copolymer poly[5,5′-(2,7-bisthiophen-2-yl-9,9-bisoctyl-9H- fluoren-7-yl)-alt-2,9-(benzo[c]thiophene-N-dodecyl-4,5-dicarboxylic imide)] and 80 wt % of PC71BM with a high open-circuit voltage (Voc) of 0.84 V.
- Li, Hairong,Sun, Shuangyong,Salim, Teddy,Bomma, Swarnalatha,Grimsdale, Andrew C.,Lam, Yeng Ming
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- Influence of alkyl substituents on the solution- and surface-organization of hexa-peri-hexabenzocoronenes
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Three hexa-peri-hexabenzocoronenes (HBCs) with branched, bulky alkyl substituents of different lengths in the periphery of the aromatic core have been synthesized to tune the self-association properties in solution. 1H NMR and photophysical mea
- Kastler, Marcel,Pisula, Wojciech,Wasserfallen, Daniel,Pakula, Tadeusz,Muellen, Klaus
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- Exceptionally long-range self-assembly of Hexa-peri-hexabenzocoronene with dove-tailed alkyl substituents
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The substitution of a hexa-peri-hexabenzocoronene by bulky, space-demanding, 2-decyltetradecyl side chains proved to be an effective procedure to influence the thermal and self-aggregation behavior. The extremely large steric requirement of the introduced
- Pisula, Wojciech,Kastler, Marcel,Wasserfallen, Daniel,Pakula, Tadeusz,Muellen, Klaus
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Read Online
- Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance
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Three lactone-based rigid semiconducting polymers were designed to overcome major limitations in the development of n-type organic thermoelectrics, namely electrical conductivity and air stability. Experimental and theoretical investigations demonstrated that increasing the lactone group density by increasing the benzene content from 0 % benzene (P-0), to 50 % (P-50), and 75 % (P-75) resulted in progressively larger electron affinities (up to 4.37 eV), suggesting a more favorable doping process, when employing (N-DMBI) as the dopant. Larger polaron delocalization was also evident, due to the more planarized conformation, which is proposed to lead to a lower hopping energy barrier. As a consequence, the electrical conductivity increased by three orders of magnitude, to achieve values of up to 12 S cm and Power factors of 13.2 μWm?1 K?2 were thereby enabled. These findings present new insights into material design guidelines for the future development of air stable n-type organic thermoelectrics.
- Alsufyani, Maryam,Stoeckel, Marc-Antoine,Chen, Xingxing,Thorley, Karl,Hallani, Rawad K.,Puttisong, Yuttapoom,Ji, Xudong,Meli, Dilara,Paulsen, Bryan D.,Strzalka, Joseph,Regeta, Khrystyna,Combe, Craig,Chen, Hu,Tian, Junfu,Rivnay, Jonathan,Fabiano, Simone,McCulloch, Iain
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supporting information
(2021/12/23)
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- Comparing the microstructure and photovoltaic performance of 3 perylene imide acceptors with similar energy levels but different packing tendencies
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While it is widely recognized that microstructure plays an important role in the performance of organic photovoltaics (OPV), systematic studies are often challenging, as varying the molecular packing through typical chemical means (such as sidechain tuning) often affects the molecular energy levels, thus preventing a clear correlation. In this work we present the synthesis of three perylene imide (PI) based electron acceptors with almost identical energy levels, but distinct packing tendencies. We confirm our initial hypothesis by measuring solution and solid-state absorption, and cyclic voltammetry as well as characterizing the films by grazing incidence wide angle X-ray scattering (GIWAXS). In a second step, we repeat the characterization of the three materials in blends with two polymer donors, namely PCDTBT or PBDBT, whose energy levels are well aligned with those of the PI acceptors, and which, additionally, exhibit different degrees of structural order. We show how the initial strong difference between acceptors is partially blurred in blends, but still critical. Finally, we correlate our structural data with OPV devices made with the corresponding six blends. Our data suggest that a good donor acceptor marriage should ensure good energy alignment but also exhibit complementary crystallization tendencies of the two components. This journal is
- Adel, Rana,Alonso-Navarro, Matías J.,Campoy-Quiles, Mariano,De La Pe?a, Alejandro,Gala, Elena,Gutierrez-Fernandez, Edgar,Harbuzaru, Alexandra,Martín, Jaime,Martinez-Ferrero, Eugenia,Ortiz, Rocío Ponce,Ramos, M. Mar,Segura, José L.,Stella, Marco
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supporting information
p. 1698 - 1710
(2022/02/17)
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- The effect of aromatic ring size in electron deficient semiconducting polymers for n-type organic thermoelectrics
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N-type semiconducting polymers have been recently utilized in thermoelectric devices, however they have typically exhibited low electrical conductivities and poor device stability, in contrast to p-type semiconductors, which have been much higher performing. This is due in particular to the n-type semiconductor's low doping efficiency, and poor charge carrier mobility. Strategies to enhance the thermoelectric performance of n-type materials include optimizing the electron affinity (EA) with respect to the dopant to improve the doping process and increasing the charge carrier mobility through enhanced molecular packing. Here, we report the design, synthesis and characterization of fused electron-deficient n-type copolymers incorporating the electron withdrawing lactone unit along the backbone. The polymers were synthesized using metal-free aldol condensation conditions to explore the effect of enlarging the central phenyl ring to a naphthalene ring, on the electrical conductivity. When n-doped with N-DMBI, electrical conductivities of up to 0.28 S cm-1, Seebeck coefficients of -75 μV K-1 and maximum Power factors of 0.16 μW m-1 K-2 were observed from the polymer with the largest electron affinity of -4.68 eV. Extending the aromatic ring reduced the electron affinity, due to reducing the density of electron withdrawing groups and subsequently the electrical conductivity reduced by almost two orders of magnitude. This journal is
- Alsufyani, Maryam,Bristow, Helen,Chen, Hu,Chen, Xingxing,Fabiano, Simone,Hallani, Rawad K.,Ji, Xudong,McCulloch, Iain,Paulsen, Bryan D.,Rivnay, Jonathan,Sirringhaus, Henning,Wang, Suhao,Xiao, Mingfei,Xu, Kai
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supporting information
p. 15150 - 15157
(2020/11/23)
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- SEMICONDUCTING POLYMER
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Compounds of formula (I) and polymers comprising at least a structure of formula (II), wherein T1 or T2 are independently of each other a group of Formula (III), Formula (iv) Qa, Qb, Qc, Qd, Qe or Qf are independently of each other O, S or NR1.
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Page/Page column 36; 37
(2017/09/19)
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- Novel alkylhalide compounds and method for preparing the same
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The present invention relates to a novel alkyl halide compound and a method for preparing the same. The alkyl halide compound according to the present invention can be applied to all polymers and single molecules which are used in an organic semiconductor, and thus the organic semiconductor materials incorporating the novel alkyl group have an improved solubility due to the novel alkyl group, thereby facilitating manufacturing of an element through solution processes of spin coating, dye casting, printing, etc. In addition, the alkyl halide compound can improve properties of the element by controlling the shape and crystallinity of a film.
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Paragraph 0093-0096
(2017/01/05)
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- Naphthalene-Functionalized, Photoluminescent Room Temperature Ionic Liquids Bearing Small Counterions
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Obtaining π-conjugated room temperature ionic liquids (RTILs) is difficult because of the relatively strong π-π interaction among the π-moieties. Existing strategies by using bulky counterions greatly hindered further property optimization and potential applications of these intriguing functional fluids through simple ion exchange. Herein, four naphthalene-functionalized, π-conjugated RTILs with small counterions (Br-) have been facilely synthesized with high yields. Our strategy is to attach branched alkyl chains to the cationic backbone of the target compounds (2 a-d), which effectively tune inter- and intramolecular interactions. Compounds 2 a-d have satisfactory thermal stability (up to 300 °C) and low melting points (-19 °C). Rheological measurements revealed the fluid character of 2 a-d, whose viscosity decrease with the increase of the alkyl chain length and temperature. The presence of the π-conjugated naphthalene moiety imparts 2 a-d photoluminescent properties in bulk solutions. Moreover, the absence of strong π-π stacking among the naphthalene units in solvent-free states enables them to be used as a new generation of photoluminescent inks.
- Zhu, Hongxia,Zhang, Geping,Chen, Mengjun,Zhou, Shengju,Li, Guihua,Wang, Xiaolin,Zhu, Qingzeng,Li, Hongguang,Hao, Jingcheng
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supporting information
p. 6286 - 6293
(2016/05/09)
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- Thieno[3,4-c]pyrrole-4,6-dione-3,4-difluorothiophene Polymer Acceptors for Efficient All-Polymer Bulk Heterojunction Solar Cells
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Branched-alkyl-substituted poly(thieno[3,4-c]pyrrole-4,6-dione-alt-3,4-difluorothiophene) (PTPD[2F]T) can be used as a polymer acceptor in bulk heterojunction (BHJ) solar cells with a low-band-gap polymer donor (PCE10) commonly used with fullerenes. The “all-polymer” BHJ devices made with PTPD[2F]T achieve efficiencies of up to 4.4 %. While, to date, most efficient polymer acceptors are based on perylenediimide or naphthalenediimide motifs, our study of PTPD[2F]T polymers shows that linear, all-thiophene systems with adequately substituted main chains can also be conducive to efficient BHJ solar cells with polymer donors.
- Liu, Shengjian,Kan, Zhipeng,Thomas, Simil,Cruciani, Federico,Brédas, Jean-Luc,Beaujuge, Pierre M.
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supporting information
p. 12996 - 13000
(2016/10/30)
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- GRAPHENE NANORIBBONS WITH CONTROLLED ZIG-ZAG EDGE AND COVE EDGE CONFIGURATION
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Provided are graphene nanoribbons with controlled zig-zag edge and cove edge configuration and methods for preparing such graphene nanoribbons. The nanoribbons are selected from the following formulae.
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(2015/09/22)
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- Novel alkylhalide compounds and method for preparing the same
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The present invention refers to new alkylene halide compound and manufacturing method relates to, alkyl halide compound the present invention according to the organic semiconductor which can be used for all new applied to monomolecular polymer and alkyl alkyl novel organic semiconductor material have been introduced having improved solubility is due to various solvent added spin coating, die casting, printing of fluid, e.g., process fabrication of one end of the end, the type and volume of the film element characteristics for modulating determined the objective compound..
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Paragraph 0087-0090
(2016/10/27)
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- Influence of side chain length and bifurcation point on the crystalline structure and charge transport of diketopyrrolopyrrole-quaterthiophene copolymers (PDQTs)
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The influence of the side chain on the molecular organization and charge transport performance of diketopyrrolopyrrole-quaterthiophene copolymers (PDQTs) was studied. It was found that, by increasing the side chain length from 2-octyldodecyl (PDQT-20) to 2-decyltetradecyl (PDQT-24), the mobility increased from 2.10 cm2 V-1 s-1 up to 3.37 cm2 V-1 s-1 in organic thin film transistors (OTFTs). The increase was found to be due to the improved surface morphology, rather than the changes in crystallinity and π-π stacking distance. A new side chain substituent, 4-decylhexadecyl, was developed for studying the effects of the bifurcation point of the branched side chains in comparison with 2-octyldodecyl and 2-decyltetradecyl. The 4-decylhexadecyl substituted PDQT (PDQT-26) showed a surge in mobility up to 6.90 cm2 V-1 s-1. The remarkably enhanced charge transport performance observed for PDQT-26 was believed to originate from its much shorter π-π distance (3.68 A) than those of PDQT-20 (3.79 A) and PDQT-24 (3.86 A). The improvement was the result of a farther distance of the bifurcation point of 4-decylhexadecyl from the polymer backbone, which could effectively minimize the steric interference of the bulky side chain branches with the backbone to facilitate the co-facial π-π stacking.
- Chen, Shaoyun,Sun, Bin,Hong, Wei,Aziz, Hany,Meng, Yuezhong,Li, Yuning
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p. 2183 - 2190
(2014/03/21)
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- Enhancing field-effect mobility of conjugated polymers through rational design of branched side chains
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The design of polymer semiconductors possessing effective π-π intermolecular interactions coupled with good solution processability remains a challenge. Structure-property relationships associated with side chain structure, π-π intermolecular interactions, polymer solubility, and charge carrier transport are reported for a donor-acceptor(1)-donor-acceptor(2) polymer: 5-Decylheptadecyl (5-DH), 2-tetradecyl (2-DT), and linear n-octadecyl (OD) chains are substituted onto a polymer backbone consisting of terthiophene units (T) between two different electron acceptors, benzothiadiazole (B), and diketopyrrolopyrrole (D), pTBTD, to afford pTBTD-5DH, pTBTD-2DT, and pTBTD-OD, respectively. In the 5-DH side chain, the branching position is remote from the polymer backbone, whereas it is proximal in 2-DT. This study demonstrates that incorporation of branched side chains where the branching position is remote from the polymer backbone merges the advantages of improved solubility from branched units with effective π-π intermolecular interactions normally associated with linear chains on conjugated polymers. pTBTD-5DH exhibits superior qualities with respect to the degree of polymerization, solution processability, π-π interchain stacking, and charge carrier transport relative to the other analogs. pTBTD-5DH exhibits a field-effect hole mobility of up to 2.95 cm2 V-1 s-1, a factor of 3-7 times that achieved with pBDT6-DT and pBDT6-OD. 5-Decylheptadecyl (5-DH), 2-tetradecyl (2-DT), and n -octadecyl (OD) side chains are substituted into pTBTD polymer backbone. The branching position is remote or close to pTBTD in 5-DH and 2-DT. 5-DH merges advantages of branched units (2-DT) for improving solubility with those of linear chains (OD) in providing effective π-π intermolecular interactions. 5-DH substituted pTBTD exhibits a field-effect hole mobility reaching 2.95 cm2 V-1 s-1.
- Fu, Boyi,Baltazar, Jose,Sankar, Ashwin Ravi,Chu, Ping-Hsun,Zhang, Siyuan,Collard, David M.,Reichmanis, Elsa
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p. 3734 - 3744
(2014/07/07)
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- Iron(II) spin crossover complexes with branched long alkyl chain
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The bzimpy iron(II) complexes, 1-3, containing branched long alkyl chains were synthesized and characterized in detail. The temperature-dependant magnetic susceptibility of 1 showed gradual spin crossover behavior from low spin to high spin state, while 2
- Lee, Young Hoon,Ohta, Asuka,Yamamoto, Yuki,Komatsu, Yasuka,Kato, Kazuya,Shimizu, Tetsuya,Shinoda, Hideaki,Hayami, Shinya
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experimental part
p. 3001 - 3005
(2012/01/12)
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- Conjugated polymers from naphthalene bisimide
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(Chemical Equation Presented) Stille coupling of regioisomerically pure dibromonaphthalene bisimides (NBI) with various stannylated thiophene-based monomers yields (very) high molecular weight donor-acceptor conjugated polymers. Electrochemical and optica
- Guo, Xugang,Watson, Mark D.
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supporting information; experimental part
p. 5333 - 5336
(2009/06/06)
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- Sulfonium salts as photoinitiators
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Sulfonium salt photoinitiator compositions, precursors useful in the preparation of such photoinitiators and the use of these photoinitiators in, e.g., UV curable adhesives, UV curable sealants, UV curable coating compositions, such as printing inks and v
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(2008/06/13)
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