Improving the Electropolymerization Properties of Fluorene-Bridged Dicarbazole Monomers through Polyfluoroalkyl Side Chains

Abstract

The facile functionalization of the fluorene scaffold at the 2,7-positions was utilized to provide access to two soluble carbazole-π-carbazole derivatives CFC-H1 and CFC-F1 featuring fully hydrogenated and polyfluorinated alkyl chains at the 9position of the fluorene π-bridging unit, respectively. The optical and electrochemical properties of the new dicarbazoles were investigated. Their electrochemical polymerization over Pt and indium tin oxide electrodes allowed the generation of electroactive polymeric films, whose physicochemical characteristics were strongly dependent on the kind of alkyl chain present on the fluorene bridge. In particular, the electropolymerization of the polyfluorinated monomer allowed the fabrication of thin films with good electrical conductivity, reversible electrochemical processes, good electrochromic properties, and enhanced water repellency with respect to its nonfluorinated analogue.

Benzothiadiazole‐Based Green Hybridized Local and Charge‐Transfer (HLCT) Fluorophores as Solution‐Processed Non‐Doped Emitters for Simple Structured Electroluminescent Devices

“…Additionally, the repeated CV scans exhibited unchanged CV traces, signifying that the generated radical cation species of both (4-(carbazol-9-yl)phenylbenzothiadiazole and 4-(7-(tertbutylcarbazol-9-yl)-fluoren-2-yl)benzothiadiazole moieties are relatively stable to radical-radical coupling reactions on the surface of glassy carbon working electrode which is often observed in most of the carbazole derivatives. [37] In our cases, the two radical cations could be stabilized by either radical delocalization along the conjugated backbone induced by the electron-accepting effect of the nearby Bz ring or deactivated or protected by the tert-butyl substituents, bringing about electrochemically stable CBzF and CBzFC. Based on the onset oxidation (E onset ox ) and reduction (E onset re ) potentials, the electrochemical bandgaps (E g ele ) of the two molecules were calculated to be 2.64 eV for CBzF and 2.45 eV for CBzFC, which are in the same trend as their optical bandgaps (E g opt = 2.49 eV for CBzF and 2.41 eV for CBzFC) estimated from the optical absorption edges of their UV-vis spectra in thin-film (Table 1).…”

Electron Donor‐Acceptor Spirobi[cyclopenta[2,1‐b : 3,4‐b′]dithiophene] Derivatives as Precursors of Electrodeposited Regioregular Thiophene‐based Polymers

“…Therefore, electrochemical deposition conditions provide an adequate surface morphology to be used in the manufacture of optoelectronic devices. The granulated surfaces evidenced by the images in Figure 4 are typical of electrodeposited films [55–58] . However, the grain size seems to be somewhat different, with better defined and larger size grains in the case of the SO7 film.…”

“…The granulated surfaces evidenced by the images in Figure 4 are typical of electrodeposited films. [55][56][57][58] However, the grain size seems to be somewhat different, with better defined and larger size grains in the case of the SO7 film. It has been reported that there is a correspondence between this kind of morphology and the conductive properties, which would position SO7 as the most conductive film.…”

Influence of Polyfluorinated Side Chains and Soft‐Template Method on the Surface Morphologies and Hydrophobic Properties of Electrodeposited Films from Fluorene Bridged Dicarbazole Monomers

“…Carbazole–Fluorene–Carbazole conjugated monomers ( CFC ) are a class of interesting precursors of electrodeposited coatings films over conductive substrates, thanks to repetitive electrochemically promoted oxidative homocoupling reactions occurring at the carbazole sites (see Figure S39, Supporting Information) [26,27] . Their molecular design easily allows to bond tailored substituents to the sp 3 carbon atom at the 9‐position of fluorene ring.…”