141215-32-9Relevant articles and documents
Potentiometric, electronic structural, and ground- and excited-state optical properties of conjugated bis[(porphinato)zinc(II)] compounds featuring proquinoidal spacer units
Susumu, Kimihiro,Duncan, Timothy V.,Therien, Michael J.
, p. 5186 - 5195 (2005)
We report the synthesis, optical, electrochemical, electronic structural, and transient optical properties of conjugated (porphinato)zinc(II)-spacer- (porphinato)zinc(II) (PZn-Sp-PZn) complexes that possess intervening conjugated Sp structures having varying degrees of proquinoidal character. These supermolecular PZn-Sp-PZn compounds feature Sp moieties {(4,7-diethynylbenzo[c] [1,2,5]thiadiazole (E-BTD-E), 6,13-diethynylpentacene (E-PC-E), 4,9-diethynyl-6,7-dimethyl[1,2,5]thiadiazolo[3,4-g]quinoxaline (E-TDQ-E), and 4,8-diethynylbenzo[1,2-c:4,5-c′]bis([1,2,5]thiadiazole) (E-BBTD-E)} that regulate frontier orbital energy levels and progressively increase the extent of the quinoidal resonance contribution to the ground and electronically excited states, augmenting the magnitude of electronic communication between terminal (5,-10,20-di(aryl)porphinato)zinc(II) units, relative to that evinced for a bis[(5,5′,-10,20-di(aryl)porphinato)zinc(II)]butadiyne benchmark (PZnE-EPZn). Electronic absorption spectra show significant red-shifts of the respective PZn-Sp-PZn x-polarized Q state (S0 → S1) transition manifold maxima (240-4810 cm-1) relative to that observed for PZnE-EPZn. Likewise, the potentiometrically determined PZn-Sp-PZn HOMO-LUMO gaps (E1/20/+ - E1/2-/0) display correspondingly diminished energy separations that range from 1.88 to 1.11 eV relative to that determined for PZnE-EPZn (2.01 eV). Electronic structure calculations provide insight into the origin of the observed PZn-Sp-PZn electronic and optical properties. Pump-probe transient spectral data for these PZn-Sp-PZn supermolecules demonstrate that the S1 → S n transition manifolds of these species span an unusually broad spectral domain of the NIR. Notably, the absorption maxima of these S 1 → Sn manifolds can be tuned over a 1000-1600 nm spectral region, giving rise to intense excited-state transitions ～4000 cm-1 lower in energy than that observed for the analogous excited-state absorption maximum of the PZnE-EPZn benchmark; these data highlight the unusually large quinoidal resonance contribution to the low-lying electronically excited singlet states of these PZn-Sp-PZn species. The fact that the length scales of the PZn-Sp-PZn species (～25 A) are small with respect to those of classic conducting polymers, yet possess NIR S1 → Sn manifold absorptions lower in energy, underscore the unusual electrooptic properties of these conjugated structures.
Design, synthesis and amplified spontaneous emission of 1,2,5-benzothiadiazole derivatives
Martín, Raúl,Prieto, Pilar,Carrillo, José R.,Rodríguez, Ana M.,De Cozar, Abel,Boj, Pedro G.,Díaz-García, María A.,Ramírez, Manuel G.
, p. 9996 - 10007 (2019)
The design, synthesis and evaluation of the amplified spontaneous emission (ASE) properties of a series of arylalkynyl-benzo[c][1,2,5]thiadiazole (BTD) and [1,2,5]thiadiazolo[3,4-g]quinoxaline (TDQ) derivatives are described. The synthetic strategy entailed the use of Sonogashira and Stille reactions based on the different aromatic natures of the two cores. The ASE properties were measured in thin polystyrene (PS) films doped with different concentrations of the synthesised compounds. BTD derivatives showed narrowing of the photoluminescence spectra (PL), thus revealing their potential laser applications. Only one TDQ derivative showed ASE. X-ray diffraction analysis was carried out to understand the observed results and to establish structure-property relationships. Molecules that showed strong molecular packing quenched the PL emission, thus giving rise to higher ASE thresholds. This is the first study in which ASE has been studied in BTD and TDQ derivatives and it represents a step forward in understanding this class of compounds for laser applications.
Synthetic Antenna Functioning As Light Harvester in the Whole Visible Region for Enhanced Hybrid Photosynthetic Reaction Centers
Hassan Omar, Omar,La Gatta, Simona,Tangorra, Rocco Roberto,Milano, Francesco,Ragni, Roberta,Operamolla, Alessandra,Argazzi, Roberto,Chiorboli, Claudio,Agostiano, Angela,Trotta, Massimo,Farinola, Gianluca M.
, p. 1614 - 1623 (2016)
The photosynthetic reaction center (RC) from the Rhodobacter sphaeroides bacterium has been covalently bioconjugated with a NIR-emitting fluorophore (AE800) whose synthesis was specifically tailored to act as artificial antenna harvesting light in the entire visible region. AE800 has a broad absorption spectrum with peaks centered in the absorption gaps of the RC and its emission overlaps the most intense RC absorption bands, ensuring a consistent increase of the protein optical cross section. The covalent hybrid AE800-RC is stable and fully functional. The energy collected by the artificial antenna is transferred to the protein via FRET mechanism, and the hybrid system outperforms by a noteworthy 30% the overall photochemical activity of the native protein under the entire range of visible light. This improvement in the optical characteristic of the photoenzyme demonstrates the effectiveness of the bioconjugation approach as a suitable route to new biohybrid materials for energy conversion, photocatalysis, and biosensing.
Organic memory effect from donor-acceptor polymers based on 7-perfluorophenyl-6H-[1,2,5]thiadiazole[3,4-g]benzoimidazole
Hu, Benlin,Wang, Chengyuan,Zhang, Jing,Qian, Kai,Lee, Pooi See,Zhang, Qichun
, p. 77122 - 77129 (2015)
A novel D-A conjugated polymer (PIBT-BDT) with 7-perfluorophenyl-6H-[1,2,5]thiadiazole[3,4-g]benzoimidazole is synthesized by the Stille coupling reaction. A memory device with PIBT-BDT as the active layer shows a large on/off ratio (>105), good endurance (>100 cycles), and long retention (>104 s). Through simulating the I-V curves and analysing energy barriers in the device structure, we suggest that the memory effect of Au/PIBT-BDT/ITO originates from the charge transfer between the strong acceptor (IBT) units and the donor BDT units.
Azacyclopentacene compound and preparation method thereof
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Paragraph 0045-0047; 0053-0060; 0061; 0064, (2021/10/30)
The azacyclopentacene compound has the chemical name of 4,9 - dibromo -6, 7 - dimethyl - [1,5] thiadiazole [3, 4-g] quinoxaline, the structural formula is shown 1, and the preparation method is as follows: S1. Under acidic conditions, 4,7 - dibromo -5, 6 -dinitrobenzene [c] [1,5] thiadiazole is reacted with a reducing agent, the reaction temperature is 45 - 55 °C, and the reaction time is 1 - 1.5h. S2. Under acidic conditions 3,4 - hexanedione reacts with the material prepared in step S1 to prepare azacyclopentacene compound, the reaction temperature is 45 - 50 °C, the reaction time is 7 - 8h, and the compound can be used for preparing large and benzene compounds. Formula 1.
Ester-substituted heterocyclic aromatic conjugated skeleton and polymer material and application thereof
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Paragraph 0033; 0051; 0056, (2021/08/19)
The invention belongs to the technical field of conjugated polymers, and particularly relates to an ester-substituted aromatic heterocyclic conjugated skeleton and a polymer material and application thereof. The ester-substituted heterocyclic aromatic conjugated skeleton and the polymer material thereof have a larger conjugated plane structure and are more beneficial to intramolecular charge transfer, and compared with the traditional heterocyclic aromatic polymer material, the ester-substituted heterocyclic aromatic conjugated skeleton has the advantages that on the basis of the original chemical structure of the polymer, two strong electron-withdrawing functional groups, namely ester groups, are introduced, so that the aromatic heterocyclic conjugated skeleton has stronger electron-withdrawing capability, the polymer has lower LUMO energy level, redder absorption spectrum and excellent long-wave range light absorption performance, and the ester-substituted aromatic heterocyclic conjugated skeleton and the polymer material thereof are used as photothermal conversion materials to be applied to the field of photoacoustic imaging, and have the advantages of higher photothermal conversion efficiency, better light stability, better imaging effect and the like.
Infrared organic light-emitting material based on benzobisthiadiazole derivative
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Paragraph 0037; 0040; 0042, (2020/03/17)
The invention discloses an infrared organic light-emitting material based on benzobisthiadiazole derivative; in the invention, a characteristic compound, in which the type of connecting groups with benzobisthiadiazole and symmetric or asymmetric bonding modes are defined, serves as the infrared organic light-emitting material, so that charge balance in a luminescent layer in an organic electroluminescent material is achieved, and the organic electronic component is improved in luminous efficiency, thermal stability, color purity and luminescent life, and the driving voltage of the device is reduced. The infrared organic light-emitting material based on benzobisthiadiazole derivative is a potential TADF (thermal-activated delayed fluorescence) material, is high in performance and high in external quantum efficiency, and has a potential application prospect.
Photosensitizer based on thiadiazolo [3, 4-g] quinoxaline structure as well as preparation method and application of photosensitizer
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Paragraph 0083; 0088; 0089, (2020/09/16)
The invention relates to a photosensitizer, which comprises a compound with a thiadiazolo[3, 4-g]quinoxaline structural unit, and the photosensitizer has structural characteristics of an intramolecular electron donor and an electron acceptor, has a relati
Thiadiazoloquinoxaline and benzodithiophene bearing polymers for electrochromic and organic photovoltaic applications
Hacioglu, Serife O.,Ataoglu, Emre,Hizalan, Gonul,Depci, Tolga,Cirpan, Ali,Toppare, Levent
, p. 937 - 946 (2019/03/11)
Two novel thiadiazoloquinoxaline and benzodithiophene (BDT) bearing copolymers were designed and synthesized. Different BDT units (alkoxy and thiophene substituted) were used as donor materials and the effect of alkoxy and thiophene substitution on the electrochemical, spectroelectrochemical and photovoltaic properties were investigated. Both polymers exhibited low oxidation potentials at around 0.90 V and low optical band gaps at around 1.00 eV due to the insertion of electron poor thiadiazoloquinoxaline unit into the polymer backbone. Both P1 (poly-6,7-bis(3,4-bis(decyloxy)phenyl)-4-(4,8-bis(nonan-3-yloxy)benzo[1,2-b:4,5-b']dithiophen-2-yl)-[1, 2, 5]thiadiazolo[3,4-g]quinoxaline) and P2 (poly- 4-(4,8-bis(5-(nonan-3-yl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophen-2-yl)-6,7-bis(3,4-bis(decyloxy)phenyl)-[1, 2, 5]thiadiazolo[3,4-g]quinoxaline) exhibited multichromic behavior with different tones of greenish yellow and gray in the neutral and fully oxidized states, respectively. In addition, both polymers revealed very high optical contrasts (～87%) in the NIR region which make these promising polymers good candidates for NIR applications. Finally, in order to explore the organic photovoltaic performances, P1 and P2 were mixed with PC71BM in the active layer of organic solar cells (OSCs) by conventional device structure. As a result P1 and P2 based devices revealed power conversion efficiencies (PCEs) of 0.33% and 0.60% respectively. However, the additive treatment enhanced PCE from 0.49 to 0.73% for P2 based devices.
Novel mitochondrial-targeted thiadiazolo[3,4-g] quinoxaline dyes as efficient photosensitizers for ultra-low dose operable photodynamic therapy
Kang, Lin,Li, Xianqiang,Zhang, Li-Peng,Zhao, Yuxia
supporting information, p. 11390 - 11393 (2019/09/30)
Two novel thiadiazolo[3,4-g]quinoxaline (TQ) photosensitizers (PSs), TQs-3 and TQs-4, were designed and synthesized. Both of them presented ultra-high singlet oxygen quantum yields under red light irradiation. By carrying out in vitro photodynamic therapy (PDT) experiments using TQs-4 loaded nanoparticles (TQs-4 NPs) to treat three kinds of tumor cell lines: 4T1, HeLa and MCF-7 cells, it was demonstrated that TQs-4 NPs had outstanding PDT efficacies. An ultra-low dose of TQs-4 (0.14 μg mL-1) can realize the death of more than 90percent HeLa cells (635 nm, 60 mW cm-2, 10 min), which indicated that TQs-4 show promising potential as a novel PS for PDT applications.
