24243-32-1

Usage

Uses

Used in Organic Electronics:
Benzo[1,2-b:6,5-b']dithiophene-4,5-dione is utilized as a key component in the development of organic semiconducting materials due to its high electron mobility, good stability, and efficient charge transport capabilities.
Used in Optoelectronic Applications:
In the field of optoelectronics, benzodithiophene-4,5-dione is employed as a building block for the synthesis of materials used in organic photovoltaics (solar cells) and organic light-emitting diodes (OLEDs), where its structural versatility and potential for functionalization contribute to the advancement of these technologies.
Used in Materials Science:
Benzo[1,2-b:6,5-b']dithiophene-4,5-dione is also used in materials science for the design and synthesis of advanced organic electronic materials, leveraging its promising properties to enhance the performance of various electronic devices.

Upstream product

• 1187970-52-0 2,7-bis-trimethylsilyl-benzo [1,2-b:6,5-b’] dithiophene-4,5-dione 
• 19690-70-1 2,2'-bithiophene-3,3'-biscarboxaldehyde 
• 7333-08-6 3,3'-Thenil 

Downstream Products

• 1407511-37-8 2,7'-bis(4-(4'-(nonyloxy)biphenyl))-benzo[2,1-b:3,4-b']dithiophene-4,5-dione 
• 1415761-37-3 5,8-dibromodithieno[3′,2’:3,4;2′′,3’’:5,6]benzo[1,2-c][1,2,5]thiadiazole 
• 1256138-50-7 dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]thiadiazole 
• 1415761-30-6 2H-dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-d][1,2,3]triazole 
• 1546975-13-6 5,8-dibromo-2-(p-octyloxyphenyl)-1-pentyldithieno[3',2':3,4:2'',3'':5,6]benzimidazole 
• 104542-90-7 ((C₄H₂S)2(CO)2)B(C₆H₅)2 
• 79845-38-8 C₁₆H₉AsClO₂S₂ 
• 79845-39-9 C₂₂H₁₄AsO₂S₂ 

Relevant academic research and scientific papers

Synthesis, characterization, charge transport, and photovoltaic properties of dithienobenzoquinoxaline- and dithienobenzopyridopyrazine-based conjugated polymers

Two donor-acceptor polymers (P1 and P2) based on dithienobenzoquinoxaline (M1) and dithienobenzopyridopyrazine (M2) as acceptor and indacenodithiophene as donor were synthesized via Stille polycondensation. The fused dithienobenzene unit in M1 and M2 units can improve the intermolecular stacking of polymer and also decrease the steric hindrance. P1, with dithienobenzoquinoxaline acceptor, shows a band gap of 1.61 eV. The band gap of P2 was reduced to 1.48 eV after changing to dithienobenzopyridopyrazine as the acceptor unit. The mobilities of P1 and P2 reach 5.6 × 10-2 and 1.5 × 10-2 cm2 V-1 s-1, respectively. The results from photovoltaic measurements showed a very promising PCE of 6.06% for the P1/PC71BM blend system without any thermal or solvent treatments, showing a great offer for the roll-to-roll manufacturing of PSCs.

Novel wide band gap polymers based on dithienobenzoxadiazole for polymer solar cells with high open circuit voltages over 1 v

A new monomer dithieno-[3′,2′:3,4;2′′,3′′:5,6]benzo[1,2-c]xadiazole (fDTBO) is first used as an electron-deficient acceptor to build D-A copolymers in a photovoltaic field. Two polymers PBDTT-fDTBO and PBDTO-fDTBO consist of fDTBO with thienyl-substituted-benzodithiophene (BDTT) or alkoxy-substituted benzodithiophene (BDTO). Both polymers show a deep HOMO around -5.5 eV with a wide band gap of over 1.9 eV. The polymer solar cells (PSCs) based on two polymers both show over 1 V high open circuit voltage (Voc) independent of polymer/PCBM ratios and solvent additives content in the PSCs active layer. The power conversion efficiency (PCE) based on PBDTT-fDTBO devices is 4.5% for single junction PSCs, and these polymers can be applied in tandem PSCs due to their wide band gap (up to 1.99 eV). This work demonstrates that the fDTBO unit is a promising building block to design wide band gap photovoltaic polymers with high Voc.

Mechanophotonics: Flexible Single-Crystal Organic Waveguides and Circuits

We present the one-dimensional optical-waveguiding crystal dithieno[3,2-a:2′,3′-c]phenazine with a high aspect ratio, high mechanical flexibility, and selective self-absorbance of the blue part of its fluorescence (FL). While macrocrystals exhibit elasticity, microcrystals deposited at a glass surface behave more like plastic crystals due to significant surface adherence, making them suitable for constructing photonic circuits via micromechanical operation with an atomic-force-microscopy cantilever tip. The flexible crystalline waveguides display optical-path-dependent FL signals at the output termini in both straight and bent configurations, making them appropriate for wavelength-division multiplexing technologies. A reconfigurable 2×2-directional coupler fabricated via micromanipulation by combining two arc-shaped crystals splits the optical signal via evanescent coupling and delivers the signals at two output terminals with different splitting ratios. The presented mechanical micromanipulation technique could also be effectively extended to other flexible crystals.

Dodecacyclic-Fused Electron Acceptors with Multiple Electron-Deficient Units for Efficient Organic Solar Cells

Fused aromatic cores in non-fullerene electron acceptors (NFEAs) play a significant role in determining their optoelectronic properties and photovoltaic performance. In this work, a dodecacyclic-fused core with three electron-deficient units is synthesized through a double intramolecular Cadogan reduction cyclization. Terminal groups with different halogen substitution (F or Cl) are grafted onto the dodecacyclic-fused core to afford MS-4F and MS-4Cl, both of which showed strong and broad absorption, narrow bandgaps around 1.40 eV, and variable molecular packing model in pristine and blend films. Photovoltaic performance of solar cells containing MS-4F and MS-4Cl as NFEAs were investigated with resultant power conversion efficiencies (PCEs) of 11.75 % and 11.79 %, respectively. The mechanism study indicates that both of PBDB-T : MS-4F- and PBDB-T : MS-4Cl-based devices displayed high hole and electron mobility values, efficient charge transfer, and low charge recombination etc. These results indicate that designing multiple-fused aromatic cores with multiple electron-deficient units is a promising strategy to obtain high-performance NFEAs.

A Facile Synthesized Polymer Featuring B-N Covalent Bond and Small Singlet-Triplet Gap for High-Performance Organic Solar Cells

High-efficiency organic solar cells (OSCs) largely rely on polymer donors. Herein, we report a new building block BNT and a relevant polymer PBNT-BDD featuring B-N covalent bond for application in OSCs. The BNT unit is synthesized in only 3 steps, leading to the facile synthesis of PBNT-BDD. When blended with a nonfullerene acceptor Y6-BO, PBNT-BDD afforded a power conversion efficiency (PCE) of 16.1 % in an OSC, comparable to the benzo[1,2-b:4,5-b′]dithiophene (BDT)-based counterpart. The nonradiative recombination energy loss of 0.19 eV was afforded by PBNT-BDD. PBNT-BDD also exhibited weak crystallinity and appropriate miscibility with Y6-BO, benefitting of morphological stability. The singlet–triplet gap (ΔEST) of PBNT-BDD is as low as 0.15 eV, which is much lower than those of common organic semiconductors (≥0.6 eV). As a result, the triplet state of PBNT-BDD is higher than the charge transfer (CT) state, which would suppress the recombination via triplet state effectively.

Dithienobenzimidazole-containing conjugated donor–acceptor polymers: Synthesis and characterization

The synthesis of two new conjugated polymers based on the relatively under-exploited monomer, 5,8-dibromo-2-[5-(2-hexyldecyl)-2-thienyl]-1H-dithieno[3,2-e:2′,3′-g]benzimidazole (dithienobenzimidazole, DTBI), and either 4,7-bis[4-hexyl-5-(trimethylstannyl)-2-thienyl]-2,1,3-benzothiadiazole (BTD) or 2,6-bis(trimethylstannyl)-4,8-bis(5-(2-ethylhexyl) thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene (BDT) is described. The polymers were synthesized via Stille polycondensation and characterized by traditional methods (1H NMR, gel-permeation chromatography, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, thermal gravimetric analysis, differential scanning calorimetry, ultraviolet–visible spectroscopy, photoluminescence, and cyclic voltammetry). Prior to their synthesis, trimer structures were modeled by DFT calculations facilitating a further understanding of the systems' electronic and geometric structure. Polymers were titrated with acid and base to take advantage of their amphiprotic imidazole moiety and their optical response monitored with ultraviolet–visible spectroscopy. Finally, pristine polymer thin-films were treated with acid and base to evaluate (de)protonation's effect on system electronics, but thin-film degradation was encountered.

New Quinoxaline-Containing Monomers for Narrow-Bandgap Polymers

Two new fused quinoxaline-containing monomers—2,3-bis(9-(2-decyltetradecyl)-9H-carbazol-3-yl)dithieno[3,2-f:2'3'-h]quinoxaline (М1) and 2,5-di(nonadecan-3-yl)bis[1,3]thiazolo[4,5-a:5',4'-c]bisthieno[3,2-h:2',3'-j]phenazine (М2)—have been synthesized in high yields of 88 and 83% as promising building blocks of D-A polymers for photovoltaic applications. The optical bandgaps, found from the absorption edge, are 2.79 and 2.88 eV, respectively. The HOMO/LUMO energies of М1 and М2 are–5.83/–2.96 and–5.83/–2.98 eV, respectively. Both monomers have low-lying HOMO levels, which is favorable for a high open-circuit voltage and a high stability in air in the development of PSCs. The Egec values of monomers М1 and М2 are 2.87 and 2.85 eV and are consistent well with the optical bandgap (2.79 and 2.88 eV, respectively).

INDACEN-4-ONE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND POLYMERS CONTAINING THEM

Indacen-4-one derivative having general formula (I) in which: - W and W1, which are the same or different, preferably the same, represent an oxygen atom; a sulfur atom; an N-R3 group in which R3 represents a hydrogen atom, or is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups; - Z and Y, which are the same or different, preferably the same, represent a nitrogen atom; or a C-R4 group in which R4 represents a hydrogen atom, or is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, linear or branched C1-C20, preferably C2-C10, alkoxyl groups, R5-O-[CH2-CH2-O]n- polyethyleneoxyl groups in which R5 is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, and n is an integer ranging from 1 to 4; -R6-OR7 groups in which R6 is selected from linear or branched C1-C20, preferably C2-C10, alkylene groups and R7 represents a hydrogen atom or is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, or is selected from R5-[-OCH2-CH2-]n- polyethyleneoxyl groups in which R5 has the same meanings as above reported and n is an integer ranging from 1 to 4, -COR8 groups in which R8 is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, -COOR9 groups in which R9 is selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, or represent a -CHO group, or a cyano group (-CN); - R1 and R2, which are the same or different, preferably the same, are selected from linear or branched C1-C20, preferably C2-C10, alkyl groups, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted heteroaryl groups, linear or branched C1-C20, preferably C2-C10, alkoxyl groups, R5-O-[CH2-CH2-O]n- polyethyleneoxyl groups in which R5 has the same meanings as above reported and n is an integer ranging from 1 to 4, -R6-OR7 groups in which R6 and R7 have the same meanings as above reported, -COR8 groups in which R8 has the same meanings as above reported, -COOR9 groups in which R9 has the same meanings as above reported, or represent a -CHO group, or a cyano group (-CN). Said indacen-4-one derivative may advantageously be used in the synthesis of electron-donor polymers, said polymers being a further object of the present invention. Said polymers may advantageously be used in the construction of photovoltaic devices (or solar devices) such as, for example, photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), on either a rigid or flexible support.

Dithienobenzochalcogenodiazole-based electron donor-acceptor polymers for organic electronics

Appositely functionalized dithienobenzo-thiadiazole and dithienobenzo-oxadiazole-monomers were prepared and used in the synthesis of conjugated electron donor-acceptor (D-A) polymers. Detailed systematic investigations were carried out to study the effects of chalcogen atoms and three donor units on the optical and electrochemical properties as well as photovoltaic and field-effect transistor performance of the D-A polymers. All polymers displayed good thermal properties. Polymers containing benzooxadiazole moiety showed deeper LUMO levels as compared to their benzothiadiazole-containing analogues, whereas those derived from weak donor unit exhibited deeper HOMO levels than those with stronger donors. Photovoltaic power conversion efficiency of over 2% and hole field-effect mobility of 2.6 × 10-2 cm2V-1s-1 and on/off ratio of over 105 were obtained. These results demonstrate that dithienobenzo-chalcogenodiazole structures are potentially useful electron acceptor building blocks for the construction of D-A polymers for organic electronics applications.

A family of donor-acceptor photovoltaic polymers with fused 4,7-dithienyl-2,1,3-benzothiadiazole units: Effect of structural fusion and side chains

A new optoelectronic building block, dithieno[3′,2′:3, 4;2″,3″:5,6]benzo[1,2-c][1,2,5]thiadiazole, was designed by applying a fusion strategy on 4,7-dithienyl-2,1,3-benzothiadazole (DTBT) and named as fDTBT. In combination with benzo[1,2-b:4,5-b′]dithiophene (BDT), fDTBT was used for the construction of a family of donor-acceptor copolymers, P(BDT n-fDTBT), with different side chains (n is carbon number of the side chain and varies from 8, 10, 12, 16, 20, to 24). It was found that the side chains have great impact on processing and photovoltaic properties of the polymers. P(BDTn-fDTBT) (n = 8, 10, and 12) bearing small alkyl side chains show poor solubility even in hot solvents. P(BDTn-fDTBT) (n = 20 and 24) have good solubility but inferior photovoltaic performance with an efficiency of 1.04% and 0.49%, respectively. Only P(BDT16-fDTBT) having 2-hexyldecyl side chain possesses both suitable solution processability and good photovoltaic properties with an efficiency around 4.36%. The comparison between P(BDT16-fDTBT) with the nonfused reference polymer P(BDT20-DTBT) reveals that the structural fusion on DTBT endows the polymer a deeper HOMO energy level and a better film morphology when blending with [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM), finally resulting in improved photovoltaic performance.