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.
Low-bandgap poly(4H-cyclopenta[def]phenanthrene) derivatives with 4,7-dithienyl-2,1,3-benzothiadiazole unit for photovoltaic cells
Kim, Jinwoo,Park, Sung Heum,Cho, Shinuk,Jin, Youngeup,Kim, Jaehong,Kim, Il,Lee, Jin Sook,Kim, Joo Hyun,Woo, Han Young,Lee, Kwanghee,Suh, Hongsuk
, p. 390 - 396 (2010)
A series of conjugated polymer bearing 4H-cyclopenta[def]phenanthrene (CPP) unit have been synthesized and was evaluated in bulk heterojunction solar cell. The alternating copolymers with CPP unit were incorporated with 4,7-dithienyl-2,1,3-benzothiadiazol
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%.
Synthesis of thiophene-based building blocks via facile α-monoiodination
Boas, Ulrik,Dhanabalan, Anantharaman,Greve, Daniel R.,Meijer
, p. 634 - 636 (2001)
A new procedure to selectively α-monoiodinate symmetrical thiophene-capped segments is described. The monoiodinated derivatives are further modified, giving access to a variety of thiophene-based building blocks, which are useful for e.g. oligomer synthesis via segmental coupling.
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
Synthesis of enantiomers of mononuclear Ru(II) complexes with 10,13-diaryl substituted dppz ligands
Li, Minna,Zhao, Ming,Peng, Shiqi
, p. 130 - 132 (2013)
An array of enantiomerically pure mononuclcear [Ru(bpy)2(dppz)] 2 + derivatives with 10,13-diaryl substituted dppz ligand has been synthesized and characterized (bpy = bipyridine, dppz = pyrido-[3,2-a:2′, 3′-c]phenazine). These new complexes exhibit substantially similar absorption spectra, resembling the parent complex [Ru(bpy)2(dppz)] 2 +, and the enantiomerically pure analogues show the similar CD spectra in buffer solution despite the structural difference.
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.
New conjugated alternating benzodithiophene-containing copolymers with different acceptor units: Synthesis and photovoltaic application
Keshtov,Marochkin,Kochurov,Khokhlov,Koukaras,Sharma
, p. 155 - 171 (2014)
Two new alternating low band gap D-A copolymers with different acceptor structures of 4,8-bis-(5-bromothiophene-2-yl)-benzo[1,2,5]thiadiazole (P1) and 4,8-dithiophene-2-yl-benzo[1,2-c;4,5-c′]-bis-[1,2,5]thiadiazole (P2) and a common BDT donor segment have been synthesized under Stille reaction conditions and characterized. The polymers showed good solubility, broad absorption bands and optical band gaps of 1.62 eV and 1.16 eV for P1 and P2, respectively. Bulk heterojunction (BHJ) polymer solar cells based on P1 and P2 as electron donors and fullerene derivatives (PC60BM and PC70BM) as acceptor were fabricated and their photovoltaic response was investigated. The overall power conversion efficieny (PCE) achieved for BHJ solar cells based on P1:PC60BM, P2:PC60BM, P1:PC70BM and P2:PC 70BM blends cast from THF solvent is about 2.17%, 0.80%, 3.45% and 1.19%, respectively. The higher PCE for the device based on P1 has been attributed to the high value of hole mobility for P1 as compared to P2 and a larger driving force i.e. LUMO-LUMO offset, for photo-induced charge transfer for P1:PCBM BHJ active layer. The PCE has been further increased up to 5.30% and 1.58% for P1:PC70BM and P2:PC70BM blends cast from DIO/THF solvent, which is attributed to the improved crystallinity and a more balanced charge transport in the device. The Royal Society of Chemistry.
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.
Strongly red-fluorescent novel donor-π-bridge-acceptor-π-bridge-donor (D-π-A-π-D) type 2,1,3-benzothiadiazoles with enhanced two-photon absorption cross-sections
Kato, Shin-Ichiro,Matsumoto, Taisuke,Ishi-I, Tsutomu,Thiemann, Thies,Shigeiwa, Motoyuki,Gorohmaru, Hideki,Maeda, Shuichi,Yamashita, Yoshiro,Mataka, Shuntaro
, p. 2342 - 2343 (2004)
Novel donor-π-bridge-acceptor-π-bridge-donor (D-π-A-π-D) type 2,1,3-benzothiadiazole fluorescent dyes connected to the N,N-diarylamino terminus via various type π-conjugate spacers exhibits large two-photon absorption cross-sections and high fluorescent quantum yields in orange-red color.
