1293389-28-2Relevant academic research and scientific papers
Synthesis of 5H-dithieno[3,2-b:2′,3′-d]pyran as an electron-rich building block for donor-acceptor type low-bandgap polymers
Dou, Letian,Chen, Chun-Chao,Yoshimura, Ken,Ohya, Kenichiro,Chang, Wei-Hsuan,Gao, Jing,Liu, Yongsheng,Richard, Eric,Yang, Yang
, p. 3384 - 3390 (2013)
We describe the detailed synthesis and characterization of an electron-rich building block, dithienopyran (DTP), and its application as a donor unit in low-bandgap conjugated polymers. The electron-donating property of the DTP unit was found to be the strongest among the most frequently used donor units such as benzodithiophene (BDT) or cyclopentadithiophene (CPDT) units. When the DTP unit was polymerized with the strongly electron-deficient difluorobenzothiadiazole (DFBT) unit, a regiorandom polymer (PDTP-DFBT, bandgap = 1.38 eV) was obtained. For comparison with the DTP unit, polymers containing alternating benzodithiophene (BDT) or cyclopentadithiophene (CPDT) units and the DFBT unit were synthesized (PBDT-DFBT and PCPDT-DFBT). We found that the DTP based polymer PDTP-DFBT shows significantly improved solubility and processability compared to the BDT or CPDT based polymers. Consequently, very high molecular weight and soluble PDTP-DFBT can be obtained with less bulky side chains. Interestingly, PDTP-DFBT shows excellent performance in bulk-heterojunction solar cells with power conversion efficiencies reaching 8.0%, which is significantly higher than PBDT-DFBT and PCPDT-DFBT based devices. This study demonstrates that DTP is a promising building block for high-performance solar cell materials.
Effective design of A-D-A small molecules for high performance organic solar cells via F atom substitution and thiophene bridge
He, Anwang,Qin, Yuancheng,Dai, Weili,Zhou, Dan,Zou, Jianping
, p. 2263 - 2265 (2019)
Three novel small molecules with acceptor-donor-acceptor (A-D-A) configuration, SBDT1, SBDT2 and SBDT3, where 4,8-bis(octyloxy)benzo[1,2-b:4,5-b′]dithiophene (BDT) as the electron-donating core connecting to thiophene-substituted benzothiadiazole (BT) as electron-withdrawing are reported. The effects of fluorine atoms on the photophysical properties by introducing different fluorine atoms into the benzothiadiazole unit were investigated. These SBDTs exhibit good thermal stability, excellent panchromatic absorption in solution and film. SBDT2 and SBDT3 with fluorine-substituted BT possess a relatively deeper the highest occupied molecular orbital (HOMO). These A-D-A type molecules were treated as donor and PC71BM as acceptor in bulk heterojunction (BHJ) small-molecule organic solar cells (SMOSCs). Among them, device based on SBDT2 gave the best device performance with a PCE of 5.06% with Jsc of 10.56 mA/cm2, Voc of 0.85 V, fill factor (FF) of 56.4%. These studies indicate that proper incorporation of fluorine atoms is an effective way to increase the efficiency of organic solar cells.
Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7% efficiency
Zhou, Huaxing,Yang, Liqiang,Stuart, Andrew C.,Price, Samuel C.,Liu, Shubin,You, Wei
, p. 2995 - 2998 (2011)
High-powered polymer: Fluorinated benzothiadiazole was incorporated into a polymer that was used in a high-performance solar cell. The model polymer 2 has decreased HOMO and LUMO energy levels and a similar band gap when compared with its nonfluorinated analogue 1. A bulk heterojunction device derived from 1 demonstrated a high power conversion efficiency of 7.2% (5.0% for 1). (Chemical Equation Presented).
Chlorination: Vs. fluorination: A study of halogenated benzo [c] [1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging
Chao, Pengjie,He, Feng,Lai, Hanjian,Lin, Li,Mo, Daize,Tian, Leilei,Zhang, Qingwen
, p. 7740 - 7748 (2020)
Red/near-infrared organic dyes are becoming increasingly widespread in biological applications. However, designing these dyes with long-wavelength emission, large Stokes shifts, and high fluorescence quantum efficiency is still a very challenging task. In this work, five donor-acceptor (D-A) red/near-infrared fluorophores based on different chlorinated/fluorinated benzo[c][1,2,5]thiadiazole units are designed and synthesized. The photophysical, theoretical calculations, and electrochemical properties explored in this study have proved that the introducing of chlorine atoms will lead to a lower HOMO level, stronger steric hindrance, and a relatively lower quantum yield in solutions. When the organic dots are fabricated, the chlorinated dots demonstrate much higher fluorescence quantum yield, larger Stokes shift, and better photostability than that of the fluorinated dots. After labeling A549 cells, all the chlorinated/fluorinated dots exhibit high red emission intensities. All these results indicated that the subtle change in the halogen atom of the benzo[c][1,2,5]thiadiazole unit is a unique method to tune the photophysical properties of those materials, and also provides good guidelines to design highly efficient red/near-infrared molecules for cellular imaging applications.
Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2
Maciejewska, Agnieszka Monika,Paprocki, Daniel,Poznański, Jaros?aw,Speina, El?bieta,Winiewska‐szajewska, Maria
, (2021)
Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.
Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications
Arslan Udum, Yasemin,Aslan, Sultan Taskaya,Bolay?r, Eda,Cevher, Duygu,Cirpan, Ali,Hizalan Ozsoy, Gonul,Toppare, Levent,Y?ld?r?m, Erol
, (2021/10/05)
A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were performed on model tetramer structures to shed light on how substituting the fluorine atom to the acceptor building block affects the structural, electronic and optical properties of the polymers. The results of computational studies were compared with experimental studies. The structure adjustment accomplished by fluorine substitution on the benzothiadiazole moiety reveals an influence on the electronic structure of polymers with a more negative HOMO energy level. A high VOC for the resulting photovoltaic device was examined for PBDTSe-FFBT. Difluorinated polymer PBDTSe-FFBT:PC71BM organic solar cell exhibited the highest photovoltaic performance of 2.63% with JSC of 7.24 mA cm-2, VOC of 0.72 V and FF of 50.6%. PBDTSe-BT:PC71BM revealed the best PCE as 2.39%, and the device reached the highest efficiency up to 1.68% for PBDTSe-FBT:PC71BM.
Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges
Karaman, Cansu Zeytun,G?ker, Seza,Hacio?lu, Serife O.,Haciefendio?lu, Tu?ba,Yildirim, Erol,Toppare, Levent
, (2021/04/23)
Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as -5.68 eV/-3.91 eV, -5.71 eV/-3.72 eV, -5.61 eV/-4.04 eV, and -5.51 eV/-3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.
Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes
Yu, Chin-Yang,Hsu, Chia-Chieh,Weng, Hsi-Chen
, p. 12619 - 12627 (2018/04/16)
Compounds consisting of unsubstituted, monofluoro and difluoro substituted benzothiadiazole bonded to two tetraphenylethenes were successfully prepared by palladium catalyzed Suzuki-Miyaura cross-coupling reaction of their corresponding co-monomers. All compounds exhibited aggregation-induced emission characteristics when the water fraction was higher than 60% in the THF/water mixtures. The emission maximum for the three compounds was blue-shifted when the water content reached 90% compared to that in THF solution. The intensity of emission maximum of difluorinated benzothiadiazole linked with two tetraphenylethenes was 2.5 times higher in 90% water compared to those in THF solution. Surprisingly, two liquid crystal phases with two distinct emission colors were observed only for the compound containing difluorinated benzothiadiazole bonded to two tetraphenylethene. All compounds showed remarkable solvatochromic properties in selected solvents with different polarities. The powder XRD results and mechanochromism of the compounds suggested that the solid state structures can change from one form to another by grinding, fuming or annealing processes.
Boron compound
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Paragraph 0101, (2017/08/23)
PROBLEM TO BE SOLVED: To provide a method for producing a boron compound represented by a formula (II) from a compound represented by a formula (I) in a short reaction time with good yield.SOLUTION: There is provided a method for producing a boron compound represented by a formula (II), the method comprising: a step of producing a first intermediate obtained by reacting a compound represented by a formula (I) and a lithium amide compound or an alkyllithium compound and a second intermediate from the first intermediate; and a step of reacting the second intermediate and an alcohol or a divalent carboxylic acid. (I) (II) [Y represents a divalent group; and Y represents a boric acid ester residue.]
Fluoro monomers, oligomers, and polymers for inks and organic electronic devices
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Page/Page column 35-36, (2016/08/07)
High performance organic photovoltaic cells based on donor acceptor polymers in the active layer. A composition comprising: at least one copolymer comprising at least one first donor moiety and at least one first acceptor moiety in the copolymer backbone, wherein the first acceptor moiety comprises at least one first ring which is bivalently linked to the copolymer backbone and at least one second ring fused to the first ring and not bivalently linked to the copolymer backbone, wherein the first ring or the second ring comprises two adjacent fluoro ring substituents, and optionally, wherein the donor comprises at least one fused ring system. High efficiency, high Voc, and a combination of both can be achieved.
