30272-74-3

Usage

Uses

Used in Organic Electronics:
Benzo[1,2-b:4,5-b']difuran-2,6(3H,7H)-dione is utilized as a precursor in the synthesis of organic electronic materials, leveraging its unique structure to contribute to the creation of devices with enhanced electronic properties.
Used in Materials Science:
In the field of materials science, benzo[1,2-b:4,5-b']difuran-2,6(3H,7H)-dione is employed as a component in the development of new materials with tailored electronic and optical characteristics, potentially leading to advances in various technological applications.
Used in Research and Development:
Due to its complex structure and limited availability, benzo[1,2-b:4,5-b']difuran-2,6(3H,7H)-dione is also used in research and development settings to explore its full potential and to understand its behavior in different chemical environments, which is essential for its safe and effective use.
Safety Considerations:
As with any chemical compound, benzo[1,2-b:4,5-b']difuran-2,6(3H,7H)-dione may present certain hazards, and safety considerations must be taken into account during its handling and use. This includes proper storage, handling procedures, and protective measures to ensure the safety of those working with the compound.

Upstream product

• 5488-16-4 2,2′-(2,5-dihydroxy-1,4-phenylene)diacetic acid 
• 106-51-4 p-benzoquinone 
• 2245-53-6 2,2'-[1,4-phenylenebis(oxy)]bisacetic acid 
• 57271-90-6 2,2'-dicyano-2,2'-(2,5-dihydroxy-p-phenylene)-di-acetic acid diethyl ester 

Relevant academic research and scientific papers

The effect of aromatic ring size in electron deficient semiconducting polymers for n-type organic thermoelectrics

N-type semiconducting polymers have been recently utilized in thermoelectric devices, however they have typically exhibited low electrical conductivities and poor device stability, in contrast to p-type semiconductors, which have been much higher performing. This is due in particular to the n-type semiconductor's low doping efficiency, and poor charge carrier mobility. Strategies to enhance the thermoelectric performance of n-type materials include optimizing the electron affinity (EA) with respect to the dopant to improve the doping process and increasing the charge carrier mobility through enhanced molecular packing. Here, we report the design, synthesis and characterization of fused electron-deficient n-type copolymers incorporating the electron withdrawing lactone unit along the backbone. The polymers were synthesized using metal-free aldol condensation conditions to explore the effect of enlarging the central phenyl ring to a naphthalene ring, on the electrical conductivity. When n-doped with N-DMBI, electrical conductivities of up to 0.28 S cm-1, Seebeck coefficients of -75 μV K-1 and maximum Power factors of 0.16 μW m-1 K-2 were observed from the polymer with the largest electron affinity of -4.68 eV. Extending the aromatic ring reduced the electron affinity, due to reducing the density of electron withdrawing groups and subsequently the electrical conductivity reduced by almost two orders of magnitude. This journal is

A BDOPV-based donor-acceptor polymer for high-performance n-type and oxygen-doped ambipolar field-effect transistors

An electron-deficient building block BDOPV is developed to construct a new donor-acceptor conjugated polymer BDOPV-2T for high-performance n-type and oxygen-doped ambipolar polymer field-effect transistors. A high electron mobility up to 1.74 cm2 V-1 s-1 is demonstrated under ambient conditions. Furthermore, the oxygen-doping effect and possible mechanism are discussed.

A bis(2-oxoindolin-3-ylidene)-benzodifuran-dione containing copolymer for high-mobility ambipolar transistors

A bis(2-oxoindolin-3-ylidene)-benzodifuran-dione (BIBDF)-based low band gap polymer (PBIBDF-BT), containing a solubilizing alkyl chain bithiophene unit as a donor, has been synthesized. The polymer with a low-lying LUMO/HOMO energy level (-4.03/-5.55 eV) exhibits efficient ambipolar charge transport. The electron and hole mobilities are as high as 1.08 and 0.30 cm2 V -1 s-1, respectively. The Royal Society of Chemistry 2014.

Vinylene and benzo[c] [1,2,5]thiadiazole: Effect of the π-spacer unit on the properties of bis(2-oxoindolin-3-ylidene)-benzodifuran-dione containing polymers for n-channel organic field-effect transistors

Two polymers based on (3E,7E)-3,7-bis(2-oxoindolin-3-ylidene)benzo[1,2-b:4,5-b′]difuran-2,6(3H,7H)-dione (BIBDF) coupled with (E)-2-(2-(thiophen-2-yl)vinyl)thiophene (TVT) or dithienylbenzothiadiazole (TBT), namely PBIBDF-TVT and PBIBDF-TBT were synthesized via the Stille coupling reaction. The effect of benzothiadiazole or vinylene-π spacer of the copolymers on optical properties, energy levels, electronic device performance and microstructure were studied. It was found that PBIBDF-TBT based OFET devices, annealed at 180 °C, showed better performance with the highest electron mobility of 2.9 × 10-2 cm2 V s-1 whereas PBIBDF-TVT polymer exhibited 5.0 × 10-4 cm2 V s-1. The two orders of magnitude higher electron mobility of PBIBDF-TBT over PBIBDT-TVT is a clear indicator of the better charge transport ability of this polymer semiconductor arising from its higher crystallinity and better donor-acceptor interaction.

Lactone Backbone Density in Rigid Electron-Deficient Semiconducting Polymers Enabling High n-type Organic Thermoelectric Performance

Three lactone-based rigid semiconducting polymers were designed to overcome major limitations in the development of n-type organic thermoelectrics, namely electrical conductivity and air stability. Experimental and theoretical investigations demonstrated that increasing the lactone group density by increasing the benzene content from 0 % benzene (P-0), to 50 % (P-50), and 75 % (P-75) resulted in progressively larger electron affinities (up to 4.37 eV), suggesting a more favorable doping process, when employing (N-DMBI) as the dopant. Larger polaron delocalization was also evident, due to the more planarized conformation, which is proposed to lead to a lower hopping energy barrier. As a consequence, the electrical conductivity increased by three orders of magnitude, to achieve values of up to 12 S cm and Power factors of 13.2 μWm?1 K?2 were thereby enabled. These findings present new insights into material design guidelines for the future development of air stable n-type organic thermoelectrics.

Multifunctional geometrical isomers of ferrocene-benzo[1,2-b:4,5-b′]difuran-2,6-(3H,7H)-dione adducts: second-order nonlinear optical behaviour and charge transport in thin film OFET devices

Geometrical isomers of a set of new ferrocene-benzo[1,2-b:4,5-b′]difuran-2,6-(3H,7H)-dione dyads were synthesized and their optical, nonlinear optical (NLO) and electrochemical properties were investigated. The compounds were fully characterized by spectroscopic data and single crystal X-ray analysis in few cases. The second-order nonlinear polarizabilities were measured in chloroform using a femtosecond hyper-Rayleigh scattering (HRS) method at 1300 nm. The dyads exhibit structure-dependent NLO properties, which could be rationalized by correlation with electrochemical and theoretical data. The (Z)-6 chromophore recorded higher βHRS values than the corresponding (E)-6 isomer, in the donor-acceptor (D-A) type dyads. Similarly, in D-A-D chromophore 7, the βHRS values of isomers follow the order (Z,Z) > (E,Z) > (E,E), which matches with the trend of the wavelength of their maximum absorption as well as an increasing band gap in that order. Owing to the inbuilt structural features, two of these D-A compounds were also explored as semiconducting materials in vacuum deposited top contact bottom gated thin film organic field-effect transistors (OFETs). Defying steric restrictions of the ferrocene unit, the triad (Z,Z)-7 depicted an unbalanced (μe: 3 × 10?3 cm?2 V?1 s?1 and μh: 7 × 10?5 cm?2 V?1 s?1) charge transport behaviour. Evaluation of the isomers of the type studied in this investigation constitutes one of very few reports, in particular this study reveals for the first time the semiconducting behaviour of thermally stable redox active Fc based semiconductors.

Electron-Deficient Poly(p-phenylene vinylene) Provides Electron Mobility over 1 cm2 V-1 s-1 under Ambient Conditions

Poly(p-phenylene vinylene) derivatives (PPVs) are one of the most widely investigated p-type polymers in organic electronics. PPVs generally exhibit electron mobilities lower than 10-4 cm2 V-1 s-1, thus hindering their applications in high-performance polymer field-effect transistors and organic photovoltaics. Herein, we design and synthesize a novel electron-deficient PPV derivative, benzodifurandione-based PPV (BDPPV). This new PPV derivative displays high electron mobilities up to 1.1 cm2 V-1 s-1 under ambient conditions (4 orders of magnitude higher than those of other PPVs), because it overcomes common defects in PPVs, such as conformational disorder, weak interchain interaction, and a high LUMO level. BDPPV represents the first polymer that can transport electrons over 1 cm2 V-1 s-1 under ambient conditions.

Colorant compounds, intermediates, and compositions

Colorants are disclosed that exhibit high color strength, bright shades, and high thermal stability. Such compounds have found application as colorants for polyethylene terephthalate (“PET”). Potential end uses include disperse dyes, non-warping pigments, decolorizable colorants, and the like. Compounds and methods for synthesis include benzodifuranone related compounds, benzene centered lactones, benzene centered lactams; benzene-centered thiolactones; naphthalene-centered lactones; naphthalene-centered lactams; naphthalene-centered thiolactones; anthraquinone-centered lactones; anthraquinone-centered lactams; anthraquinone-centered thiolactones; anthracene-centered lactones; anthracene-centered lactams; anthracene-centered thiolactones; hetero-aromatic-centered lactones; hetero-aromatic centered lactams and hetero-aromatic centered thiolactone compounds, and the like. Furthermore, resins such as PET or other polymeric resins containing the compounds are disclosed.