Synthesis of an H-aggregated thiophene–phthalimide based small molecule via microwave assisted direct arylation coupling reactions

High open circuit voltage organic solar cells based upon fullerene free bulk heterojunction active layers

“…These values were comparable with those reported by our group and others. 39,63 Table 1 shows the melting and crystallization temperatures of the drop-cast blends. In comparison with the endotherms of the pure materials, melting temperatures of the blends were lower than the two components.…”

“…Both spectra were comparable with those reported elsewhere in the literature. 39,45,46 The absorption maximum of PthTh 2 Pth at 380 nm was assigned to the -* transition. The absorption onset at 514 nm corresponds to an optical gap of 2.4 eV.…”

An Electron‐Deficient Small Molecule Accessible from Sustainable Synthesis and Building Blocks for Use as a Fullerene Alternative in Organic Photovoltaics

“…[54] Further modification can occur at the nitrogena tom, which can be functionalized with alkyl side chains to influence solubility ands elf-assembly. Isoindigo has been included within the structure of many electron acceptor organic polymers, [56,62,63] while phthalimide has an extensiveh istory as an electron transport material; [43,45,47,64] thus, al ogical combinations for new electron deficient materials. [57][58][59] To extend the chromophore, the isoindigo core is flanked with electron-rich thiophene (Th)b ridging units to tailor the band gap and promote backbonep lanarity,w hile also effectively applying the intramolecular donor-acceptor approach of charge transfer for the design of p-conjugated materials.…”

“…The commercial availability of brominated starting indoles makes this av ery attractive synthesis, occurring in near-quantitative yields of ab rominated product already functionalized for subsequentreactions. [43,[70][71][72][73][74][75] The procedure was adjusted accordingly for microwavei rradiation, which was found to dramatically reduce reactiont ime from 24 hc onventional heatingt oj ust 22 minutes, returning comparable yields (90 %, 0.41 g).C onsidering the significant success of transitioning from conventional heatingt om icrowavea ssisted synthesis, subsequent reactions were optimized under microwavei rradiation when possible. Successfulm icrowave-assisted synthesis vastly reduces the long reactiont imes that typically plaguec onventional procedures while also providing more uniform heating, often resulting in higher yields.…”

“…Phthalic anhydride derivatives are common plasticizers anda re widely availablef rom the xylenes feedstock, while phthalimide is produced almoste xclusively from phthalic anhydride and ammonia and constitutes an important intermediate in the production of agricultural pesti-An electron-deficient small molecule accessible from sustainable isoindigo and phthalimide building blocks was synthesized via optimized synthetic procedures that incorporate microwave-assisted synthesis and ah eterogeneousc atalystf or Suzuki coupling, and direct heteroarylation carbon-carbon bond forming reactions. [43][44][45][46][47][48] Herein we detail an optimized and sustainable synthesis, materialc haracterization, and preliminaryO PV characterization of an isoindigo-based small molecule incorporating electrondeficient phthalimide end-capping units. Further investigation of the material revealed ad iffering solid-state morphology with the use of three well-known processing conditions:t hermala nnealing, solvent vapor annealing and small volumef ractionso f1 , 8- cides and pharmaceuticals.…”