1269004-56-9

Usage

Uses

Used in Organic Electronics Industry:
3,6-bis(2,2'-bithiophene-5-yl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione is used as a key component in the development of organic solar cells due to its efficient charge transport and light absorption properties.
Used in Photovoltaic Devices:
In the photovoltaic industry, 3,6-bis(2,2'-bithiophene-5-yl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione serves as a promising candidate for the production of high-performance organic photovoltaic materials, contributing to the advancement of solar energy technology.
Used in the Production of Flexible Solar Cells:
3,6-bis(2,2'-bithiophene-5-yl)-2,5-bis(2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione is utilized as a vital ingredient in the creation of flexible solar cells, thanks to its good solubility and film-forming properties, which are crucial for the fabrication of efficient and adaptable solar energy systems.

Upstream product

• 1185885-86-2 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione 
• 1269004-43-4 2,5-bis(2-ethylhexyl)-3,6-bis(5-iodothiophene-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione 
• 37496-13-2 2-(trimethylstannyl)thiophene 
• 1003-31-2 thiophene-2-carbonitrile 
• 6165-68-0 thiophene boronic acid 
• 1000623-95-9 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 54663-78-4 tributyl(thien-2-yl)stannane 

Relevant academic research and scientific papers

Towards Highly-Efficient Phototriggered Data Storage by Utilizing a Diketopyrrolopyrrole-Based Photoelectronic Small Molecule

A cooperative photoelectrical strategy is proposed for effectively modulating the performance of a multilevel data-storage device. By taking advantage of organic photoelectronic molecules as storage media, the fabricated device exhibited enhanced working parameters under the action of both optical and electrical inputs. In cooperation with UV light, the operating voltages of the memory device were decreased, which was beneficial for low energy consumption. Moreover, the ON/OFF current ratio was more tunable and facilitated high-resolution multilevel storage. Compared with previous methods that focused on tuning the storage media, this study provides an easy approach for optimizing organic devices through multiple physical channels. More importantly, this method holds promise for integrating multiple functionalities into high-density data-storage devices.

Phthalimide and Naphthalimide end-Capped Diketopyrrolopyrrole for Organic Photovoltaic Applications

Two small molecules named PI-DPP and NI-DPP with a DPP core as the central strong acceptor unit and phthalimide/naphthalimide as the terminal weak acceptor were designed and synthesized. The effects of terminal phthalimide/naphthalimide units on the thermal behavior, optical and electrochemical properties, as well as the photovoltaic performance of these two materials were systematically studied. Cyclic voltammetry revealed that the lowest unoccupied molecular orbitals (LUMO) (~ -3.6 eV) of both molecules were intermediate to common electron donor (P3HT) and acceptor (PCBM). This indicated that PI-DPP and NI-DPP may uniquely serve as electron donor when blended with PCBM, and as electron acceptor when blended with P3HT, where sufficient driving forces between DPPs and PCBM, as well as between P3HT and DPPs should be created for exciton dissociation. Using as electron donor materials, PI-DPP and NI-DPP devices exhibited low power conversion efficiencies (PCEs) of 0.90% and 0.76% by blending with PCBM, respectively. And a preliminary evaluation of the potential of the NI-DPP as electron acceptor material was carried out using P3HT as a donor material, and P3HT:NI-DPP device showed a PCE of 0.6%, with an open circuit voltage (VOC) of 0.7 V, a short circuit current density (JSC) of 1.91 mA?cm-2, and a fill factor (FF) of 45%.

Substituent-eliminable diketopyrrolopyrrole derivative, organic semiconductor material precursor solution, organic semiconductor material, and organic semiconductor material film

A substituent-eliminable diketopyrrolopyrrole derivative represented by the following formula (I) is provided. In the formula (I), R represents a substituted or unsubstituted alkyl group; X represents a substituted or unsubstituted alkyl group; Ar represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group; and n represents an integer of from 1 to 4.

Air-stable ambipolar organic field-effect transistors based on naphthalenediimide-diketopyrrolopyrrole copolymers

Two air-stable polymeric semiconductors were rationally designed and synthesized, namely PNDI-DPP and PNDI-T(DPP)T, containing naphthalenediimide (NDI) units and diketopyrrolopyrrole (DPP). The coplanar thiophene-substituted DPP moieties act as donors rather than acceptors, even though DPP is an electron-deficient core. In a bottom-gate/top-contact device architecture, the effect of changing the number of thiophene linkers on the performance of the two completely different OFETs was investigated. PNDI-T(DPP)T presented unipolar p-type behaviour with an average hole mobility of 0.02 cm2 V-1 s-1, while PNDI-DPP exhibited ambipolar transport with average electron and hole mobilities of 5.7 × 10-3 and 1.6 × 10-3 cm2 V-1 s-1, respectively. Moreover, OFETs based on the two polymers showed good air-stability with negligible changes after being stored under ambient conditions for over 3 months. This journal is

Synthesis and characterization of optical and redox properties of bithiophene-functionalized diketopyrrolopyrrole chromophores

A series of six new 2,2′-bithiophene-functionalized diketopyrrolopyrrole (DPP) dyes 7a-f bearing different electron-donating and electron-withdrawing substituents at the terminal thiophene units was synthesized by palladium-catalyzed cross-coupling reactions. The to date unknown diiodinated DPP 2 and the corresponding boronic ester derivative 3 could be prepared in high yields, and these are shown to be versatile building blocks for the synthesis of DPP-based molecular materials by Negishi, Stille, and Suzuki coupling. The influence of the peripheral substituents on the optical and electrochemical properties of the present series of DPP dyes 7a-f were investigated by UV/vis and steady-state fluorescence spectroscopy and cyclic voltammetry, revealing an appreciable effect on the electronic nature of these dyes. The diamino-substituted DPP derivative 7e exhibits a strong absorption band reaching in the near-infrared (NIR) region, which is a highly desirable feature for application in organic photovoltaics.