267220-47-3

Usage

Uses

Used in Organic Electronics:
Tetracenequinone is utilized as a semiconducting material in the development of electronic devices such as organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs). Its unique structure and properties contribute to the performance and efficiency of these devices.
Used in Chemical Synthesis:
As a building block, Tetracenequinone is employed in the synthesis of more complex organic compounds. Its reactivity and structural features make it a valuable component in creating advanced materials with specific properties for various applications.
Used in Antioxidant and Anticancer Research:
Tetracenequinone has been studied for its potential antioxidant properties, which could be beneficial in protecting against oxidative stress and related conditions. Additionally, its anticancer properties are of interest, as it may offer a new avenue for the development of cancer treatments by targeting specific biological pathways involved in cancer progression.

Upstream product

• 73540-76-8 N,N-diethylfuran-3-carboxamide 
• 14757-80-3 N,N-dimethylfuran-3-carboxamide 

Downstream Products

• 1404437-40-6 2,6-(trimethyltin)-4,8-bis(4-decylphenylethynyl)-benzo[1,2-b:4,5-b']difuran 
• 1404437-39-3 2,6-dibromo-4,8-bis(4-decylphenylethynyl)-benzo[1,2-b:4,5-b']difuran 
• 1404437-38-2 4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']difuran 
• 1391764-83-2 2,6-bis(trimethyltin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]difuran 
• 1618093-18-7 C₄₄H₄₄BrNO₄ 
• 1618093-17-6 C₅₄H₆₀BrNO₂Si₂ 
• 1618093-22-3 C₄₉H₄₇NO₅S 
• 1618093-21-2 C₅₉H₆₃NO₃SSi₂ 

Relevant academic research and scientific papers

Synthesis of copolymers based on benzo[1,2-b:4,5-b′]difuran and fluorinated quinoxaline derivatives and their photovoltaic properties

Two alternating polymers based on two-dimensional conjugated benzo[1,2-b:4,5-b′]difuran and fluorinated quinoxaline derivatives were synthesized. Their structures are poly{4,8-bis(2,3-(dioctyl)thiophen-5-yl)-benzo[1,2-b:4,5-b′]difuran-alt-5,8-bis(thiophen-2-yl)-6-fluoro-2,3-bis(3-octyloxyphenyl) quinoxaline} (P1, mono F) and poly{4,8-bis(2,3-(dioctyl)thiophen-5-yl)-benzo[1,2-b:4,5-b′]difuran-alt-5,8-bis(thiophen-2-yl)-6,7-difluoro-2,3-bis(3-octyloxyphenyl) quinoxaline} (P2, double F). UV-vis absorption measurements show that the difluorinated polymer P2 exists a higher absorption in comparison with the mono fluorinated polymer P1 either in the solution or in the film. Electrochemical measurements confirm that the polymer P2 displays low energy levels (-5.30 eV and -3.25 eV) of both highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) in comparison with those of P1 (-5.25 eV and -3.20 eV). Photovoltaic cells with conventional device configuration of ITO/PEDOT:PSS/polymer:PC71BM/PFN/Al were fabricated. The power conversion efficiency (PCE) of the optimized polymer solar cells (PSCs) based on P1 reaches 2.22% with a current density of 5.28 mA/cm2. However, a high PCE of 4.44% with a high current density of 8.74 mA/cm2 was obtained for the double fluorinated polymer P2 based device.

Method for efficiently preparing high-quality benzodifuranone

The invention discloses a method for efficiently preparing high-quality benzodifuranone, belonging to the field of optimization of post-treatment routes of organic synthesis. The method comprises thefollowing specific steps: (1) putting N,N-diethyl-furan-3-formamide into anhydrous THF, dropwise adding a hexane solution of n-BuLi at 4 DEG C to -10 DEG C in a protective atmosphere, and after the addition is finished, raising the temperature to room temperature and performing stirring for 4.0 h to 6.0 h; (2) pouring a mixed solution obtained in the previous step into deionized water, and performing stirring for 2.0-5.0 hours at room temperature; (3) removing deionized water and THF by rotating through a rotary evaporator; (4) pouring a residual viscous material into a sand core funnel provided with a separation layer, and performing washing with dichloromethane multiple times until the color of a filtrate becomes transparent; (5) removing dichloromethane in the filtrate in the manner ofrotating through the rotary evaporator; and (6) carrying out drying in vacuum to obtain the high-quality benzodifuranone.

Benzo[1,2-b:4,5-b′]dithiophene and benzo[1,2-b:4,5-b′]difuran based organic dipolar compounds for sensitized solar cells

Novel organic dyes that consist of either a benzo[1,2-b:4,5-b′] dithiophene or a benzo[1,2-b:4,5-b′]difuran core exhibited remarkable solar-to-energy conversion efficiency in dye-sensitized solar cells. The planar geometry of bridge moiety and its bulky substituents helped the dyes to form a high quality monolayer on the surface of titanium oxide. A typical device displayed photon-to-current conversion efficiency 60% in the region of 380-575 nm, a short-circuit photocurrent density 13.45 mA cm-2, an open-circuit photovoltage 0.72 V, and a fill factor 0.63, corresponding to an overall conversion efficiency 6.12%. In a test of using deoxycholic acid as a co-absorbent, an improvement of quantum efficiencies 8.37% was observed for certain compounds. However, for others the quantum efficiency decreased in 6.60-7.91%. The latter result indicated that the quality of some films cannot be further improved by the addition of deoxycholic acid. The photophysical properties were analyzed with the aid of TDDFT.

A new benzo[1,2-b:4,5-b′]difuran-based copolymer for efficient polymer solar cells

A new donor-acceptor type copolymer, namely poly{4,8-bis(2-ethylhexyloxy) benzo[1,2-b:3,4-b′]difuran-alt-6-octylnaphtho[2,3-c]thiophene-4,9-dione} (PBDFNTDO) was synthesized by a Stille coupling reaction and characterized by 1H NMR, GPC, TGA, UV-Vis absorption spectroscopy and cyclic voltammetry. PBDFNTDO is readily soluble in common organic solvents with a number-average molecular weight (Mn) of 10.7 kDa mol-1 and a polydispersity index of 1.71. TGA analysis shows the copolymer exhibits good thermal stability with 5% weight loss at a temperature of 341 °C. PBDFNTDO possesses a broad absorption band at 300-750 nm with an optical bandgap of 1.65 eV. Cyclic voltammetry gives HOMO and LUMO energy levels of -5.33 eV and -3.40 eV, respectively. The hole mobility of PBDFNTDO:PC71BM (1:1.5, w/w) reaches up to 5.0 × 10-3 cm2 V-1 s -1 by the space-charge-limited current (SCLC) method. A polymer solar cell with the configuration of ITO/PEDOT:PSS/PBDFNTDO:PC71BM (1:1.5, w/w)/Ca/Al demonstrates a promising power conversion efficiency of 4.71% under the illumination of AM 1.5 G, 100 mW cm-2.

Synthesis and optoelectronic properties of novel benzodifuran semiconducting polymers

Two new semiconducting polymers poly{4,8-bis(4-decylphenylethynyl)benzo[1, 2-b:4,5-b']difuran} (P1) and poly {4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5- b']difuran-alt-4,8-bis(4-decylphenylethynyl)benzo[1,2-b:4,5-b']dithiophene} (P2) have been synthesi

Synthesis of a 4,8-dialkoxy-benzo[1,2-b:4,5-b′]difuran unit and its application in photovoltaic polymer

A new building block of benzo[1,2-b:4,5-b′]difuran (BDF) was firstly designed and synthesized. The newly designed unit was applied for constructing a new photovoltaic low band gap polymer, PBDFDTBT, which exhibited promising power conversion efficiency of 5.0%. The Royal Society of Chemistry 2012.

Conjugated and nonconjugated substitution effect on photovoltaic properties of benzodifuran-based photovoltaic polymers

In order to investigate the influence of two-dimensional (2D) conjugated structure on photovoltaic properties of benzo[1,2-b:4,5-b']difuran (BDF)-based polymers, two low band gap photovoltaic polymers, named PBDFTT-CF-O and PBDFTT-CF-T, were designed and synthesized. These two polymers have the same backbones and different side groups. Although these two polymers show similar optical band gaps (ca. 1.5 eV), the polymer with alkylthienyl side groups, PBDFTT-CF-T, exhibits stronger absorption in long wavelength direction than the polymer with alkoxyl side groups, PBDFTT-CF-O. Meanwhile, PBDFTT-CF-T exhibits a HOMO level of -5.21 eV, which is 0.23 eV lower than that of PBDFTT-CF-O due to weaker electron-donating ability of alkylthienyl side groups than that of aloxyl side groups. The hole mobility of the blend of PBDFTT-CF-T/PC71BM (1:1.5, w/w) is 0.128 cm2 V-1 s-1, which is 1 order of magnitude higher than that of the blend of PBDFTT-CF-O/PC 71BM. Density functional theory (DFT) model shows thiophene pendants on dithienyl-BDF are more coplanar than it on dithienyl-BDT. These results indicate that the 2D-conjugated structure is helpful for molecular structure design of the BDF-based polymers in enhancing the intermolecular π-π stacking and improving charge transport property. Furthermore, the photovoltaic devices based on these two polymers show similar short circuit density and fill factor values, while the open circuit voltage of the PBDFTT-CF-T-based device is 0.78 V, which is 0.15 V higher than that of the PBDFTT-CF-O-based device. Therefore, the efficiencies of the devices based PBDFTT-CF-T/PC71BM and PBDFTT-CF-O/PC71BM are 6.26% and 5.22%, respectively. The results in this work demonstrate that the weak electron-donating ability of alkylthienyl side groups can be seen as an effective strategy to improve photovoltaic properties of the BDF-based polymers and the 2D-conjugated molecular structure is favorable to improve hole mobility.