An N-annulated perylene butyl tetraester for alcohol processed semiconducting organic thin films

Abstract

Herein, we report on the design and synthesis of an N-annulated perylene butyl tetraester (PTEN-H) for use in alcohol processed semiconducting films. PTEN-H was contrasted with the known N-annulated perylene diimide (PDIN-H) where the former has ring-opened imide positions which in turn lowers the electron affinity (i.e., rendering hole transporting) and improves polar green solvent solubility. PTEN-H can be solubilized in 1-butanol up to 10 mg/mL with gentle heating and can be spin-cast or slot-die coated to form uniform thin films on glass and/or plastic substrates. Organic field-effect transistors (OFETs) were fabricated using PTEN-H in the active material layer which was deposited from solution using 1-butanol as the solvent. While hole mobilities were achieved (0.39 x 10-4 cm2/Vs), blending the molecular material with a previously reported green solvent processable semiconducting polymer, IIG20-OH, was done to boost performance. This led to increased mobilities for not only the native molecular PTEN-H material, but for the native IIG20-OH polymer as well. Furthermore, a blend of PTEN-H and IIG20-OH were slot-die coated onto a polyethylene terephthalate (PET) substrate giving uniform thin films suitable for large area device fabrication.

Methods of changing low molecular weight gel properties through gelation kinetics

“…Using heat-cool cycles When LMWGs are heated, this increases their solubility and therefore, the molecules are more dispersed in solution due to reduced intermolecular interactions. 69 As a result, these molecules may reassemble differently after cooling as they are molecularly dissolved. Thus, the kinetics will be affected by both the temperature the solution is heated to and the cooling rate, directly influencing the structures formed.…”

Perylene-Based Smart Fluoroprobe with Dual Function: Ratiometric Response toward Hazardous Organic Peroxides and Pure White Light Generation via Self-Assembly

“…Encouraged by the abovementioned findings, in this work, we have designed and synthesized a fluorescent probe containing boronate ester conjugated with perylene (dibutyl perylene-3,4-dicarboxylate) with improved solubility, , abbreviated as PBE . The boronate group in our designed fluorescent probe PBE was chosen to functionalize at the peri position of the perylene core because of its highly selective reaction toward reactive oxygen/nitrogen species. − The fluorescent probe PBE shows a very fast response toward hazardous peroxide present in old ethereal solvents (like THF, 1,4-dioxane, and diethyl ether) via a visible color change from green to pale yellow.…”

Bright green electroluminescence with an EQE of 4.6% from a host–guest OLED fabricated from an unsymmetric liquid crystalline N-annulated perylene ester imide as a dopant

“…This combination positions them as frontrunners for propelling the domain of organic electronics forward. The last two decades have witnessed increased efforts devoted to the exploration of N -annulated perylene derivatives that can be utilized in the area of supramolecular self-assembly, 9 donor–acceptor (D-A) systems, 10 organic field effect transistors (OFETs), 6 c ,11 organic solar cells (OSCs), 12 dye-sensitized solar cells (DSSCs), 13 and organic light-emitting diodes (OLEDs). 7 a ,14…”