- A Distannylated Monomer of a Strong Electron-Accepting Organoboron Building Block: Enabling Acceptor–Acceptor-Type Conjugated Polymers for n-Type Thermoelectric Applications
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Acceptor–acceptor (A-A) copolymerization is an effective strategy to develop high-performance n-type conjugated polymers. However, the development of A-A type conjugated polymers is challenging due to the synthetic difficulty. Herein, a distannylated monomer of strong electron-deficient double B←N bridged bipyridine (BNBP) unit is readily synthesized and used to develop A-A type conjugated polymers by Stille polycondensation. The resulting polymers show ultralow LUMO energy levels of ?4.4 eV, which is among the lowest value reported for organoboron polymers. After n-doping, the resulting polymers exhibit electric conductivity of 7.8 S cm?1 and power factor of 24.8 μW m?1 K?2. This performance is among the best for n-type polymer thermoelectric materials. These results demonstrate the great potential of A-A type organoboron polymers for high-performance n-type thermoelectrics.
- Deng, Sihui,Dong, Changshuai,Liu, Jun,Meng, Bin,Wang, Lixiang
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p. 16184 - 16190
(2021/06/18)
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- A method for synthesizing DBTPD
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The invention discloses a synthetic method of 1,3-dibromo-5-alkyl-4H-thiophene [3,4-c]-pyrroles-4,6(5H)-dione (DBTPD), which is characterized by comprising the following steps: taking 3,4-thiophene dimethylbenzene anhydride and alkylamine as raw materials, taking toluene as a solvent, reacting for 15-24 hours under 90-130 DEG C and then cooling to room temperature, then adding thionyl bromide and organic base under 0 DEG C, stirring for 1-5 hours under room temperature, and heating to 110-130 DEG C and reacting for 15-24 hours. The method can realize one-step synthesis, further separation and purification of an intermediate are not required; thionyl bromide during a synthesis process has dehydration effect and has effect as a brominating agent, anhydrous organic base is taken as a catalyst, so that usage of strong acid such as concentrated sulfuric acid and trifluoroacetic acid can be avoided, reaction security is greatly increased, and the products yield by the method can reach 90%.
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Paragraph 0038; 0040; 0042
(2017/02/17)
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- Thieno[3,4- c ]pyrrole-4,6-dione-based polymer semiconductors: Toward high-performance, air-stable organic thin-film transistors
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We report a new p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stille coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (~1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest Egopt in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituents (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of ~0.6 cm2 V-1 s-1 is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.
- Guo, Xugang,Ortiz, Rocio Ponce,Zheng, Yan,Kim, Myung-Gil,Zhang, Shiming,Hu, Yan,Lu, Gang,Facchetti, Antonio,Marks, Tobin J.
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p. 13685 - 13697
(2011/10/09)
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- Synthesis and characterization of new thieno[3,4-c]pyrrole-4,6-dione derivatives for photovoltaic applications
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A new class of low-bandgap copolymers based on benzodithiophene (BDT) and thieno[3,4-c]pyrrole-4,6-dione (TPD) units is reported. Chemical modifications of the conjugated backbone promote both high molecular weights and processability while allowing for tuning of the electronic properties. Copolymers with substituted thiophene spacers (alkyl chains facing the BDT unit) or unsubstituted thiophene spacers tend to have low power conversion efficiencies (PCE less than 1%) due to a bad morphology of the active layer, whereas copolymers with substituted thiophene spacers (alkyl chains facing TPD unit) show enhanced morphology and PCEs up to of 3.9%. Finally, BDT-TPD copolymers without any thiophene spacers still show the best performances with power conversion efficiencies up to 5.2%. The synthesis and characterization of new electroactive and photoactive copolymers based on benzodithiophene (BDT) and thieno[3,4-c]pyrrole-4,6-dione (TPD) units are described. The copolymers are synthesized with or without thiophene spacers in order to tune the electronic properties and to control the morphology of the active layer in bulk heterojunction solar cells. The potential of these new materials in photovoltaic devices is investigated.
- Najari, Ahmed,Beaupre, Serge,Berrouard, Philippe,Zou, Yingping,Pouliot, Jean-Remi,Lepage-Perusse, Charlotte,Leclerc, Mario
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p. 718 - 728
(2012/01/06)
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- Low bandgap polymers with benzo [1,2-b:4,5-b′] dithiophene and bisthiophene-dioxopyrrolothiophene units for photovoltaic applications
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New donor/acceptor polymers PBDTTPT1 and PBDTTPT2 with alternating benzodithiophene (BDT) and bisthiophene-dioxopyrrolothiophene (TPT) units were synthesized by Stille coupling reaction. The polymers had optical bandgaps of 1.78 and 1.82 eV, and HOMO energy levels of -5.30 and -5.35 eV for PBDTTPT1 and PBDTTPT2, respectively. Polymeric solar cell devices based on these copolymers as donors and PC71BM as acceptor showed the highest open circuit voltage of 0.95 V and power conversion efficiency of 2.68% under the illumination of AM 1.5, 100 mW/cm2.
- Zhang, Guobing,Fu, Yingying,Xie, Zhiyuan,Zhang, Qing
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p. 415 - 421
(2012/01/05)
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- DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME
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The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.
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- DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME
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The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.
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Page/Page column 18; 19
(2008/12/08)
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- New regiosymmetrical dioxopyrrolo- and dihydropyrrolo-functionalized polythiophenes
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(Chemical Equation Presented) We present the synthesis of two N-alkylated poly(dioxopyrrolothiophene)s and two N-alkylated poly(dihydropyrrolothiophene)s with potential application in the field of conducting polymers. The polymers are synthesized from the corresponding 2,5-dibromothiophenes by an Ullmann-type polymerization and a Stille-type polymerization, respectively. The two N-alkylated poly(dihydropyrrolothiophene)s are the first examples of amino-functionalized polythiophenes built from regiosymmetrical thiophene monomers.
- Nielsen, Christian B.,Bjornholm, Thomas
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p. 3381 - 3384
(2007/10/03)
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