Electrochemical Synthesis, Deposition, and Doping of Polycyclic Aromatic Hydrocarbon Films

Abstract

Polycyclic aromatic hydrocarbons (PAHs) are employed as organic semiconductors because their delocalized πelectron systems and strong intermolecular interactions endow them with an exceptional charge-transport ability. However, the deposition of PAHs from solution onto high-quality thin films is often difficult. Here, we report a one-step electrochemical method to synthesize and deposit unsubstituted PAHs, starting from twisted oligophenyl precursors. The cyclodehydrogenated products were analyzed by matrix-assisted laser-desorption time-of-flight mass spectrometry as well as Fourier transform infrared and Raman spectroscopy. With this electrosynthesis and deposition, the PAHs stack into compact and ordered supramolecular structures along the π−π direction to form thin films with controllable thicknesses and doping levels. The direct fabrication of PAH films opens new pathways toward PAH-based optoelectronic devices.

In-situ electropolymerized bipolar organic cathode for stable and high-rate lithium-ion batteries

“…Completely utilizing the advantages of organic electrode materials is still a significant challenge. Recently, a novel preparation method, namely, insitu electropolymerization has been reported for the fabrication of polymer electrodes [30,31]. Traditional methods of polymer electrode fabrication require presynthesized polymer materials, and it is difficult to realize uniform distribution of these materials and conductive agents.…”

Scholl reaction as a powerful tool for the synthesis of nanographenes: a systematic review

“…In this methodology, anodic oxidation was used in order to replace already existing chemical oxidizing agents used in the Scholl reaction for the formation of a new C–C bond between the two arene units. The electrochemical oxidative characteristics of the triangle-shaped precursor 207 and the ribbon-shaped precursor 209 ( Scheme 90 ) 123 were first studied by cyclic voltammetry (CV) at a scan rate of 0.05 V s −1 using glassy carbon as a working electrode. The formation of π-conjugated discs of PAHs dramatically decreased the solubility, causing precipitation under the formation of homogeneous thin films in the neutral state.…”

Multi‐Redox Active Carbons and Hydrocarbons: Control of their Redox Properties and Potential Applications

“…Recently, Müllen's group reported the electrochemical synthesis and deposition of polycyclic aromatic hydrocarbons (PAHs) [92] . They succeeded in forming thin films of PAHs such as C 60 H 24 , C 78 H 26 , and C 96 H 30 by the electrochemical oxidative cyclodehydrogenation of each precursor in CH 2 Cl 2 solutions.…”