Air stable electron-transporting and ambipolar bay substituted perylene bisimides

Reghu, Renji R.; Bisoyi, Hari Krishna; Gražulevičius, Juozas V.; Anjukandi, Padmesh; Gaidelis, Valentas; Jankauskas, Vygintas

doi:10.1039/c1jm11091h

Cited by 58 publications

(39 citation statements)

References 46 publications

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“…The TPEPPDI solution could emit strong red fluorescence at 640 nm, further verifying its highly twisted architecture. [14b,14c] For TPAPPDI, similar to literature results, [20] the fluorescence emission was weak due to intramolecular electron transfer effect.…”

Section: Optical Propertiessupporting

confidence: 81%

Pyrene‐Fused Perylene Diimides: New Building Blocks to Construct Non‐Fullerene Acceptors With Extremely High Open‐Circuit Voltages up to 1.26 V

et al. 2017

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Great efforts have been devoted to seeking alternative non‐fullerene acceptors for efficient polymer solar cells (PSCs). Achieving a high open‐circuit voltage (Voc) is quite challenging but is essential for practical application. Here, pyrene‐fused perylene diimide was first used as a periphery building block to construct non‐fullerene acceptors. Due to the high‐lying lowest unoccupied molecular orbitals (LUMOs) as well as balanced transport properties, the normal devices with the acceptors exhibited ultrahigh Voc values of up to 1.26 V. In addition, the achieved power‐conversion efficiency (PCE) of 5.10% is among the highest values for non‐fullerene PSCs with a Voc > 1.20 V, indicating that the pyrene‐fused perylene diimide (PDI) unit is a useful building block for the design of non‐fullerene PSCs with high Voc values. This study could benefit the realization of both a high PCE and Voc in PSCs.

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Section: Optical Propertiessupporting

confidence: 81%

Pyrene‐Fused Perylene Diimides: New Building Blocks to Construct Non‐Fullerene Acceptors With Extremely High Open‐Circuit Voltages up to 1.26 V

et al. 2017

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“…2,6-Bis(trimethyltin)-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene (>98%, compound 5) was purchased from Shenzhen Derthon Optoelectronic Materials Science & Technology Co., LTD (China). The syntheses of compound 1-4 were from the reported literature, 9,17,22,25 and detailed in Supporting Information. Three conjugated polymers were synthesized by Stille coupling reaction.…”

Section: Methodsmentioning

confidence: 99%

Conjugated polymers based on modified benzo[1,2-b:4,5-b′]dithiophene and perylene diimide derivatives: Good optical properties and tunable electrochemical performance

et al. 2015

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Three original conjugated polymers were devised and synthesized via the alternating conjugated polymerization of the electron-donating monomer of the modified benzo[1,2-b:4,5-b']dithiophene (BDT) and electronaccepting monomers of perylene diimide (PDI), dithienyl-perylene diimide (DTPDI) and dithienocoronene diimide (DTCDI), respectively. The synthesized conjugated polymers presented excellent thermal stability (T d >400 o C) as well as broad absorption in visible region and narrow gap of energy level (1.80 to 2.01 eV). Moreover, P(BDT-DTCDI) exhibited strong fluorescence properties ( =736 nm with excitation at 680 nm). According to the theoretical calculations, P(BDT-PDI) and P(BDT-DTPDI) displayed significant polymer backbone torsion (41.44 o and 39.64 o ), and P(BDT-DTCDI) had highly coplanar backbone with negligible angle between BDT and DTCDI. The results indicated that P(BDT-DTCDI) had potential applications in the fields of organic thin-film transistors (OTFTs) and fluorescence materials, and P(BDT-PDI) and P(BDT-DTPDI) could be used as a stable n-type semiconductor for polymer solar cells.

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“…Synthesized dyes should have suitable thermal stabilities at industrial process temperatures to be used as color filter colorants. It has been found that dye aggregation has a significant effect on the thermal stabilities of dyes [16]. Dye aggregation primarily occurs due to (1) p-p stacking interactions between aromatic rings, (2) packing of molecules with planar structures, (3) intermolecular interactions, such as Van der Waals and dipole-dipole interactions between large molecules or those containing polar substituents, and (4) intermolecular hydrogen bonding.…”

Section: As Shown Inmentioning

confidence: 99%

Synthesis and characterization of novel perylene dyes with new substituents at terminal-position as colorants for LCD color filter

Kim

Choi

Namgoong

et al. 2015

J Incl Phenom Macrocycl Chem

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Six novel red perylene dyes were synthesized by modifying the bay-and terminal-positions of perylene main body to improve the optical performances of liquid crystal display (LCD) color filters. The absorption properties, solubility in industrial solvents and thermal stabilities of the dyes were examined to evaluate the dyes for dye-based LCD color filter. Mill bases and spin-coated color filters were formulated and fabricated using the synthesized dyes. Transmittance, dye aggregation and thermal stabilities of the prepared color filters were investigated using a color spectrophotometer. Geometric structures of the synthesized dyes were optimized by using Gaussian program. Five of the synthesized dyes showed acceptable optical properties as colorants for LCD color filters. Also, the synthesized dyes and prepared color filters exhibited suitable thermal stability for the application. Furthermore, the prepared color filters exhibited superior transmittances than pigment-based color filters at 650 nm. Their physical properties were closely related with chemical structures investigated by geometry optimization.

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Air stable electron-transporting and ambipolar bay substituted perylene bisimides

Cited by 58 publications

References 46 publications

Pyrene‐Fused Perylene Diimides: New Building Blocks to Construct Non‐Fullerene Acceptors With Extremely High Open‐Circuit Voltages up to 1.26 V

Pyrene‐Fused Perylene Diimides: New Building Blocks to Construct Non‐Fullerene Acceptors With Extremely High Open‐Circuit Voltages up to 1.26 V

Conjugated polymers based on modified benzo[1,2-b:4,5-b′]dithiophene and perylene diimide derivatives: Good optical properties and tunable electrochemical performance

Synthesis and characterization of novel perylene dyes with new substituents at terminal-position as colorants for LCD color filter

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