Pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells

Abstract

We introduce two novel solution-processable electron acceptors based on an isomeric core of the much explored diketopyrrolopyrrole (DPP) moiety, namely pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP). The newly designed and synthesized compounds, 6,6′-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione] (NAI-IsoDPP-NAI) and 5,5′-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)isoindoline-1,3-dione] (PI-IsoDPP-PI) have been synthesized via Suzuki couplings using IsoDPP as a central building block and napthalimide or phthalimide as end-capping groups. The materials both exhibit good solubility in a wide range of organic solvents including chloroform (CF), dichloromethane (DCM), and tetrahydrofuran (THF), and have a high thermal stability. The new materials absorb in the wavelength range of 300–600 nm and both compounds have similar electron affinities, with the electron affinities that are compatible with their use as acceptors in donor-acceptor bulk heterojunction (BHJ) organic solar cells. BHJ devices comprising the NAI-IsoDPP-NAI acceptor with poly(3-n-hexylthiophene) (P3HT) as the donor were found to have a better performance than the PI-IsoDPP-PI containing cells, with the best device having a VOC of 0.92 V, a JSC of 1.7 mAcm−2, a FF of 63%, and a PCE of 0.97%.

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

“…These modifications can introduce motifs that change the molecule’s properties and/or generate the possibility of obtaining polymeric chains. NAI-IsoDPP-NAI and PI-IsoDPP-PI were synthesized by Suzuki coupling reactions to introduce napthalimide or phthalimide as end-capping groups [ 134 ]. By using a Stille coupling reaction with organotin derivatives of thiophene, it was possible to introduce a different number of thiophene rings in the backbone [ 135 ].…”

Synthesis and Nanoarchitectonics of Novel Squaraine Derivatives for Organic Photovoltaic Devices

“…To obtain good performance with the OPVs, the electron donor absorbers are used in a bulk heterojunction (BHJ) configuration (maximizing the specific surface of the interface) with fullerene-based electron donors [ 6 ]. One of the most promising ways to boost the PCE of the OPV was found through the incorporation of non-fullerene and small molecule donors and acceptors, which exhibit high absorption spectra, resulting in high photocurrents [ 7 , 8 ], with PCEs above 18% in state-of-the-art solar cells [ 9 , 10 , 11 ], bringing them closer to the market. The most important factors affecting OPV performance are traps and recombination, charge carrier mobility, charge carrier density, and parasitic resistances.…”

Recent advances on visible light pyrrole-derived photoinitiators of polymerization

“…Pyrrole is a heterocyclic five-membered ring compound in which the involvement of the lone pair electrons of nitrogen to the aromaticity of pyrrole makes this heterocycle an excellent electron donating group when combined with the appropriate group. Pyrrole is extensively used in Organic Electronics for the design of semiconductors for organic field effect transistors, [230,231] as active layers for organic photovoltaics, [232][233][234], for the design of dyes with solvatochromic properties, [235] the design of dyes with non-linear optical properties [236][237][238][239] or electrochromes. [240] Recently, pyrrole was investigated in the photopolymerization field and used as an elemental building block for the design of dyes of various structures.…”