165190-76-1Relevant articles and documents
Benzochalcogendiazole-based conjugated molecules: Investigating the effects of substituents and heteroatom juggling
Patel, Heta A.,Bhanvadia, Viraj J.,Mande, Hemant M.,Zade, Sanjio S.,Patel, Arun L.
, p. 9467 - 9478 (2019)
A convenient and effective synthetic approach for benzochalcogendiazole-based small molecules has been achieved using polyaniline (PANI)-anchored palladium as a heterogeneous catalyst. The photophysical properties of the synthesized benzochalcogendiazole-based small molecules, having different terminal substituents, have been compared. Moreover, the structural aspects, including the packing patterns and non-bonding interactions of the conjugated molecules, have been investigated using the single crystal X-ray diffraction (SCXRD) technique.
A solution-processable deep red molecular emitter for non-doped organic red-light-emitting diodes
Wang, Zhiming,Lu, Ping,Xue, Shanfeng,Gu, Cheng,Lv, Ying,Zhu, Qing,Wang, Huan,Ma, Yuguang
, p. 356 - 363 (2011)
A new solution-processable deep red emitter, TCTzC, containing dithienylbenzothiadiazole unit and four alkyl-linked peripheral carbazole groups, is designed and synthesized in high yield by Suzuki coupling reaction. The four peripheral carbazole substituents enhance the hole-transport ability, glass transition temperature, decompose temperature and film forming ability of TCTzC. The single-layered device based on TCTzC shows saturated deep red electroluminescence with a CIE coordinate of (0.70, 0.30). The current efficiency and quantum efficiency of TCTzC is two times higher than the compound without the four peripheral carbazole groups. The higher device performance is obtained when TPBi is applied and the external quantum efficiency could reach to 0.93%.
Structure modification and annealing effect of polymer bulk heterojunction solar cells based on polyfluorene derivatives
Lee, Jung-Feng,Hsu, Steve Lien-Chung,Lee, Po-I,Chuang, Hung-Yi,Chen, Jen-Sue,Chou, Wei-Yang
, p. 4618 - 4625 (2011)
Three low bandgap polyfluorene copolymers containing a donor-acceptor-donor moiety have been synthesized via Suzuki and Stille polymerization reactions. Their bandgaps and molecular energy levels (highest occupied molecular orbital and lowest unoccupied molecular orbital) varied with different polymerization methods. The molecular weight of the copolymer increased significantly through copolymerizing with a monomer having a long alkyl side chain. In order to investigate their photovoltaic properties, polymer solar cell devices based on the copolymers were fabricated with a structure of indium tin oxide/poly(styrene sulfonic acid)-doped poly(ethylene dioxythiophene)/copolymers:[6,6]-phenyl-C61- butyric acid methyl ester (PCBM)/LiF/Al under the illumination of AM 1.5G, 100 mW/cm2. We found that the annealing temperature had a profound effect on the power conversion efficiency (PCE) of the devices with a blend of poly[9,9-didodecylfluorene-alt-(bis-thienylene) benzothiadiazole] (PF12-TBT) and PCBM. The PCE of the solar cell based on PF12-TBT/PCBM (1:4) annealing at 70 °C for 20 min was 4.13% with an open-circuit voltage (Voc) of 1.02 V, fill factor of 55.9%, and a short-circuit current (Jsc) of 7.24 mA/cm2. Copyright
Combination of donor characters in a donor-acceptor-donor (DAD) type polymer containing benzothiadiazole as the acceptor unit
Sendur, Merve,Balan, Abidin,Baran, Derya,Karabay, Baris,Toppare, Levent
, p. 1877 - 1885 (2010)
A benzothiadiazole bearing donor-acceptor-donor (D-A-D) type monomer (M3) was synthesized using the combination of 3, 4- ethylenedioxythiophene (EDOT) and thiophene donor units to understand the effect of donor strength on the optoelectronic and electrochemical properties. The resulting monomer was polymerized electrochemically (P3) and compared with its symmetrical thiophene (P1) and EDOT (P2) bearing homologues whether there exists a combination of the electrochemical and optical characteristics. Also, copolymer studies were performed with symmetrical thiophene (M1) and EDOT (M2) containing monomers in order to compare the results with P3. Cyclic voltammetry (CV) and spectroelectrochemistry results revealed that P3 is a low band gap polymer (1.18 eV) having both p-and n-type property which is superior to the copolymers synthesized using M1 and M2.
Easily attainable phenothiazine-based polymers for polymer solar cells: Advantage of insertion of S,S-dioxides into its polymer for inverted structure solar cells
Kim, Gyoungsik,Yeom, Hye Rim,Cho, Shinuk,Seo, Jung Hwa,Kim, Jin Young,Yang, Changduk
, p. 1847 - 1857 (2012)
Two donor-(D-) acceptor (A) type polymers based on a soluble chromophore of phenothiazine (PT) unit that is a tricyclic nitrogen-sulfur heterocycle, have been synthesized by introducing an electron-deficient benzothiadiazole (BT) building block copolymerized with either PT or phenothiazine-S,S-dioxide (PT-SS) unit as an oxidized form of PT. The resulting polymers, PPTDTBT and PPTDTBT-SS are fully characterized by UV-vis absorption, electrochemical cyclic voltammetry, X-ray diffraction (XRD), and DFT theoretical calculations. We find that the maximum absorption of PPTDTBT is not only markedly red-shifted with respect to that of PPTDTBT-SS but also its band gap as well as molecular energy levels are readily tuned by the insertion of S,S-dioxides into the polymer. The main interest is focused on the electronic applications of the two polymers in organic field-effect transistors (OFETs) as well as conventional and inverted polymeric solar cells (PSCs). PPTDTBT is a typical p-type polymer semiconductor for OFETs and conventional PSCs based on this polymer and PC71BM show a power conversion efficiency (PCE) of 1.69%. In case of PPTDTBT-SS, the devices characteristics result in: (i) 1 order of magnitude higher hole mobility (μ = 6.9 × 10-4 cm2 V-1 s -1) than that obtained with PPTDTBT and (ii) improved performance of the inverted PSCs (1.22%), compared to its conventional devices. Such positive features can be accounted for in terms of closer packing molecular characteristics owing either to the effects of dipolar intermolecular interactions orientated from the sulfonyl groups or the relatively high coplanarity of PPTDTBT-SS backbone.
A low band gap donor-acceptor copolymer containing fluorene and benzothiadiazole units: Synthesis and photovoltaic properties
Pei, Jianing,Wen, Shanpeng,Zhou, Yinhua,Dong, Qingfeng,Liu, Zhaoyang,Zhang, Jibo,Tian, Wenjing
, p. 385 - 393 (2011)
A new low band gap copolymer containing dialkylfluorene and 4,7-dithienyl-2,1,3-benzothiadiazole (TBT), poly(fluorenevinylene-alt-4,7- dithienyl-2,1,3-benzothiadiazole) (PF-TBT) was synthesized by Heck cross-coupling polymerization. The copolymer is soluble in common organic solvents such as chloroform, tetrahydrofuran and chlorobenzene. The TGA result indicated that the copolymer possesses good thermal stability. The absorption, electrochemical and photovoltaic properties of PF-TBT were investigated and compared with those of poly(fluorenevinylene-alt-4,7-diphenyl-2,1,3- benzothiadiazole) (PF-DBT) whose structure is similar to PF-TBT. The copolymer exhibited a broad absorption band with an absorption edge close to 700 nm and an optical band gap of 1.82 eV. Cyclic voltammetry studies indicated that the relatively low HOMO energy level assured a higher open circuit voltage (V oc) when PF-TBT is used as the donor material in a photovoltaic cell. The bulk heterojunction (BHJ) solar cell using PF-TBT as the donor and [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as the acceptor with the structure of ITO/PEDOT:PSS/copolymer:PCBM/LiF/Al, exhibited a Voc of 0.86 V, short-circuit current density (Jsc) of 3.97 mA cm -2, fill factor (FF) of 0.35, and a power conversion efficiency (PCE) of 1.18% under one sun of AM 1.5 solar simulator illumination (100 mW cm -2).
A polymer gel electrolyte to achieve ≥6% power conversion efficiency with a novel organic dye incorporating a low-band-gap chromophore
Kim, Jeum-Jong,Choi, Hyunbong,Lee, Ji-Won,Kang, Moon-Sung,Song, Kihyung,Kang, Sang Ook,Ko, Jaejung
, p. 5223 - 5229 (2008)
A quasi-solid-state dye-sensitized solar cell with novel organic sensitizers incorporating a benzothiadiazole chromophore showed excellent long-term stability, which exhibited 10% decrease during the 1000 h light soaking; the optimized cell gave a short circuit photocurrent density of 12.03 mA cm-2, an open circuit voltage of 0.720 V and a fill factor of 0.76, corresponding to an overall conversion efficiency of 6.61% under standard global AM 1.5 solar conditions. The Royal Society of Chemistry 2008.
Synthesis of thieno[3,4-b]pyrazine-based and 2,1,3-benzothiadiazole-based donor-acceptor copolymers and their application in photovoltaic devices
Zhou, Erjun,Cong, Junzi,Yamakawa, Shimpei,Wei, Qingshuo,Nakamura, Motoshi,Tajima, Keisuke,Yang, Chunhe,Hashimoto, Kazuhito
, p. 2873 - 2879 (2010)
Two kinds of thieno[3,4-6]pyrazine-based monomers, 2,3-dimethyl-5,7-di(2- bromothien-5-yl)-thieno[3,4-b]pyrazine and 2,3-diphenyl-5,7-di(2-bromothien-5- yl)-thieno[3,4-p]pyrazine, were synthesized via an improved synthetic route. These two monomers and 4,7-di(2-bromothien-5-yl)-2,l,3-benzothiadiazole were copolymerized with three donor segments (fluorene, carbazole, and indolocarbazole) separately by a Suzuki cross-coupling reaction to give six types of 5,7-dithien-2-yl-thieno[3,4-p]pyrazine (DTTP)-based donor- acceptor (D-A) copolymers (TP1-6) and three types of 5,7-dithien-2-yl-2,l,3- benzothiadiazole (DTBT)-based D-A copolymers (PF-DTBT, PC-DTBT, and PIC-DTBT). The optical properties, electrochemical behavior, and energy levels of these nine copolymers were investigated. The photovoltaic performance of the copolymers was compared and discussed considering their energy levels.
A versatile approach to organic photovoltaics evaluation using white light pulse and microwave conductivity
Saeki, Akinori,Yoshikawa, Saya,Tsuji, Masashi,Koizumi, Yoshiko,Ide, Marina,Vijayakumar, Chakkooth,Seki, Shu
, p. 19035 - 19042 (2012)
State-of-the-art low band gap conjugated polymers have been investigated for application in organic photovoltaic cells (OPVs) to achieve efficient conversion of the wide spectrum of sunlight into electricity. A remarkable improvement in power conversion efficiency (PCE) has been achieved through the use of innovative materials and device structures. However, a reliable technique for the rapid screening of the materials and processes is a prerequisite toward faster development in this area. Here we report the realization of such a versatile evaluation technique for bulk heterojunction OPVs by the combination of time-resolved microwave conductivity (TRMC) and submicrosecond white light pulse from a Xe-flash lamp. Xe-flash TRMC allows examination of the OPV active layer without requiring fabrication of the actual device. The transient photoconductivity maxima, involving information on generation efficiency, mobility, and lifetime of charge carriers in four well-known low band gap polymers blended with phenyl-C61-butyric acid methyl ester (PCBM), were confirmed to universally correlate with the PCE divided by the open circuit voltage (PCE/Voc), offering a facile way to predict photovoltaic performance without device fabrication.
Synthesis and photovoltaic studies on novel fluorene based cross-conjugated donor-acceptor type polymers
Sharma, Bhavna,Alam, Firoz,Dutta, Viresh,Jacob, Josemon
, p. 42 - 50 (2017)
Direct arylation polymerization (DAP) is emerging as a promising green, cheap, simple, and efficient environment friendly method for synthesizing conjugated polymers without involving any organometallic reagent. We report fluorene based novel cross-conjugated alternate and random copolymers for polymer solar cells (PSCs), which were synthesized by DAP and/or Yamamoto polymerization under appropriate reaction conditions to obtain high molecular weight. These cross-conjugated polymers possess absorption maxima in the range of 490–520 nm and have narrow band gap (1.7–2.05 eV) which is suitable for bulk heterojuntion (BHJ) type organic solar cells. Among the synthesized polymers, the highest number average molecular weight (Mn) i.e. 43.1 kg mol?1 was obtained for polymer P2b (poly((9H-fluoren-9-ylidene)methylene)bis((2-ethylhexyl)sulfane)-alt-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole)), and so good polymeric films were formed for P2b. Thus, BHJ films were prepared for P2b for device performance studies and the morphology of these films was studied by atomic force microscopy (AFM). Polymer P2b was blended with the fullerene derivative [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) in different ratios and under the illumination of solar simulator with Air Mass global (AM 1.5G) irradiated at 100 mW cm?2. Power conversion efficiency (PCE) of 1.4% has been achieved for BHJs in ratio of 1:2 of P2b: PC71BM in simply processed devices. This result indicates that cross-conjugated polymers can be tapped as potential donors for BHJs as the PCE obtained is the highest among this type of cross-conjugated polymers.
New narrow-bandgap polymer composed of benzobis(1,2,5-thiadiazole) and thiophenes
Karikomi, Michinori,Kitamura, Chitoshi,Tanaka, Shoji,Yamashita, Yoshiro
, p. 6791 - 6792 (1995)
-
Synthesis and characterization of star-shaped donor-acceptor-donor structures
Pelz, Simon,Zhang, Jinming,Kanelidis, Ioannis,Klink, Dennis,Hyzak, Lukas,Wulf, Volker,Schmitz, Oliver J.,Gasse, Jan-Christoph,Frahm, Ronald,Puetz, Andreas,Colsmann, Alexander,Lemmer, Uli,Holder, Elisabeth
, p. 4761 - 4769 (2013)
A Sonogashira coupling reaction led to star-shaped 1,3,5-tris({5-[7- (thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl]thiophen-2-yl}ethynyl)benzene derivatives. The star-shaped molecules were optically analyzed, and - depending on their substitution pattern - they displayed bathochromically shifted absorptions, which were compared to their nonlinked arm precursors. The materials displayed a highly interesting morphology in bulk when blended with [6,6]-phenyl-C61-butyric acid methyl ester (PCBM). One derivative formed columnar structures and revealed prospective use in photodiodes. Copyright
Highly π-extended polymers based on phenanthro-pyrazine: Synthesis, characterization, theoretical calculation and photovoltaic properties
Wang, Zhiming,Gao, Zhao,Feng, Ying,Liu, Yulong,Yang, Bing,Liu, Dandan,Lv, Ying,Lu, Ping,Ma, Yuguang
, p. 6191 - 6199 (2013)
Two novel narrow bandgap conjugated polymers containing phenanthro-pyrazine unit have been successfully synthesized by the Stille coupling reaction. Comparing to the common polymers containing dithiophen-quinoxaline or dithiophen-thieno[3,4-b]pyrazine moi
Highly Efficient Luminescent Solar Concentrators Based on Benzoheterodiazole Dyes with Large Stokes Shifts
Gao, Sheng,Balan, Bamisha,Yoosaf, Karuvath,Monti, Filippo,Bandini, Elisa,Barbieri, Andrea,Armaroli, Nicola
, p. 11013 - 11023 (2020)
Five extended π-conjugated systems with electron donor (D) and acceptor (A) moieties have been synthesized. Their basic D-A-D structural motif is a benzothiadiazole unit symmetrically equipped with two thiophene rings (S2T). Its variants include 1) the same molecular framework in which sulfur is replaced by selenium (Se2T), also with four thiophene units (Se4T) and 2) a D’-D-A-D system having a N-carbazole donor moiety at one end (CS2T) and a D’-D-A-D-A’ array with a further acceptor carbonyl unit at the other extremity (CS2TCHO). The goal is taking advantage of the intense luminescence and large Stokes shifts of the five molecules for use in luminescent solar concentrators (LSCs). All of them exhibit intense absorption spectra in the UV/Vis region down to 630 nm, which are fully rationalized by DFT. Emission properties have been studied in CH2Cl2 (298 and 77 K) as well as in PMMA and PDMS matrices, measuring photoluminescence quantum yields (up to 98 percent) and other key optical parameters. The dye–PMMA systems show performances comparable to the present state-of-the-art, in terms of optical and external quantum efficiencies (OQE=47.6 percent and EQE=31.3 percent, respectively) and flux gain (F=10.3), with geometric gain close to 90. LSC devices have been fabricated and tested in which the five emitters are embedded in PDMS and their wave-guided VIS luminescence feeds crystalline silicon solar cells.
Organic dyes end-capped with perfluorophenyl anchors: Synthesis, electrochemical properties and assessment of sensitization capacity of titania photoanodes
Giannopoulos, Panagiotis,Raptis, Dimitrios,Theodosiou, Krystallia,Andreopoulou, Aikaterini K.,Anastasopoulos, Charalampos,Dokouzis, Alexandros,Leftheriotis, George,Lianos, Panagiotis,Kallitsis, Joannis K.
, p. 167 - 179 (2018)
In the present work, organic sensitizers are synthesized and attached on TiO2 photoanodes via Ti-O-C bonds. All sensitizers, designed for this purpose are symmetrical and have two perfluorophenyl end groups, which can lead to stable non-hydroly
Triazole derivative containing boron-nitrogen group, polymer and preparation methods and applications of triazole derivative and polymer
-
Paragraph 0052; 0055-0056, (2020/07/07)
The invention belongs to the technical field of organic photoelectricity, and discloses a triazole derivative containing a boron-nitrogen group, a polymer and preparation methods and applications of the triazole derivative and the polymer. The chemical st
