Pyrene-1,5,6,10-tetracarboxyl diimide: a new building block for high-performance electron-transporting polymers

Abstract

Both naphthalene and perylene derivatives bearing six-membered-ring dicarboximide groups are proven valuable modules for preparing organic electron-transporting semiconductors. However, obtaining their analogue with pyrene appeared challenging, as all previous endeavors...

Imide‐Functionalized Fluorenone and Its Cyanated Derivative Based n‐Type Polymers: Synthesis, Structure–Property Correlations, and Thin‐Film Transistor Performance

“…Clearly, the highly planar framework of both FOI and FCNI can facilitate strong π-π interaction which is beneficial to the charge transport. [19] The ultraviolet-visible (UV/Vis) absorption and photoluminescence (PL) spectra of C4FOI and C4FCNI were investigated; the C4FOI solution in DCM exhibits a strong absorption band in the range of 300-350 nm and C4FCNI shows red-shifted absorption compared to C4FOI (Figure 3a) with the absorption in the range of 300-400 nm. Besides, a very weak absorbance in the range of 400-500 nm (Figure S33) of the spectrum found for C4FIDCN is attributed to intramolecular charge transfer (ICT) transitions between the core unit and the dicyanovinyl group.…”

Synthesis and charge-transport properties of novel π-conjugated polymers incorporating core-extended naphtho[2,1-b:3,4-b′]dithiophene diimides

“…The combined benefits of large π-extended conjugation and the near-coplanar backbone observed here enable the polymeric main-chains to achieve effective intermolecular interactions or uniform solid-state organizations, generally both of which facilitate their film crystallization and charge carrier transport. 1,61 As for the three polymeric models, the largest coefficients in HOMO orbitals are distributed over all the molecular backbones, indicating good backbone conjugation for such polymer systems. In addition, a similar distribution characteristic can be observed for their LUMO clouds that are solely localized on the central NTI acceptor unit.…”

Electron-Transporting Conjugated Polymers from Novel Aromatic Five-Membered Diimides: Naphtho[1,2-b:4,3-b′]-dithiophene and -Diselenophene Diimides

“…The utilization of these species in donor–acceptor (D–A)-conjugated polymers has also received increasing attention during the past few decades owing to their high electron deficiencies, desirable optoelectronic properties, high carrier mobilities, as well as fine-tunable solubility and solid-state packing via imide N -alkylation . These types of polymers, therefore, are heavily applied in a majority of solution-processable organic optoelectronic devices, such as organic light-emitting diodes, organic solar cells (OSCs), organic field-effect transistors (OFETs), , and organic thermoelectrics …”

“…17 The utilization of these species in donor−acceptor (D−A)-conjugated polymers has also received increasing attention during the past few decades owing to their high electron deficiencies, desirable optoelectronic properties, high carrier mobilities, as well as fine-tunable solubility and solid-state packing via imide N-alkylation. 18 These types of polymers, therefore, are heavily applied in a majority of solution-processable organic optoelectronic devices, such as organic light-emitting diodes, 19 organic solar cells (OSCs), 20 organic field-effect transistors (OFETs), 21,22 and organic thermoelectrics. 23 It is widely accepted that the intrinsic energy levels of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of aromatic imides/ diimides have an important influence on charge transport behaviors of the resulting polymers, 1 whose comprehensive properties are highly related to the structural differences, such as the size and numbers of imide rings, parent aromatic cores, and comonomer units.…”