Fluorenone

About: Fluorenone is a research topic. Over the lifetime, 1067 publications have been published within this topic receiving 17162 citations. The topic is also known as: Diphenylene ketone & 9-Oxofluorene.

Luminescence of molecular and block copolymeric 2,7-Bis(phenylethenyl)-fluorenones; identifying green-band emitter sites in a fluorene-based luminophore

Abstract: 2,7-Bis(3,4,5-trimethoxyphenylethenyl)fluorenone (OFOPV) and a segmented oligomer analogue linking OFOPV units with polymethylene flexible spacersalt-poly(2,6-dimethoxylphenylene-4-vinylene-[9-fluorenone-2-yl-7-vinylene]3,5-dimethoxyphenylene-4-[1,6-hexanedioxyl]) (pFOPV)were synthesized and their luminescence properties studied. Solution-phase photoluminescence (PL) of OFOPV and pFOPV shows concentration-dependent relative intensities of a fine-structured higher energy band and a featureless lower energy band, consistent with solution excimer formation. Neat film PL and electroluminescence (EL) spectra using 100% OFOPV and pFOPV emitter layers show red emission bands (λmax ∼ 610 nm). Solid film PL spectra of OFOPV diluted in PMMA or Zeonex are significantly blue-shifted relative to the neat film spectra. PL and EL spectra of 2,7-bis(3,4,5-trimethoxyphenylethenyl)-9,9-diethylfluorene (OFPV) blended with <1% by weight of OFOPV gives significant green region (g-band) emission in addition to the normal blue ...

Self-assembly polymorphism of 2,7-bis-nonyloxy-9-fluorenone: solvent induced the diversity of intermolecular dipole-dipole interactions.

Abstract: In this present work, a scanning tunneling microscope (STM) operated under ambient conditions was utilized to probe the self-assembly behavior of 2,7-bis-nonyloxy-9-fluorenone (F–OC9) at the liquid–solid (l/s) interface. On the highly oriented pyrolytic graphite (HOPG) surface, two-dimensional (2D) polymorphism with diversity of intermolecular dipole interactions induced by solvent was found. Solvents ranged from hydrophilic solvating properties with high polarity, such as viscous alkylated acids, to nonpolar alkylated aromatics and alkanes. 1-Octanol and dichloromethane were used to detect the assembly of F–OC9 at the gas–solid (g/s) interface. The opto-electronic properties of F–OC9 were determined by UV-vis and fluorescence spectroscopy in solution. Our results showed that there were tremendous solvent-dependent self-assemblies in 2D ordering for the surface-confined target molecules. When a homologous series of alkanoic acids ranging from heptanoic to nonanoic acid were employed as solvents, the self-assembled monolayer evolved from low-density coadsorbed linear lamellae to a semi-circle-like pattern at relatively high concentrations, which was proven to be the thermodynamic state as it was the sole phase observed at the g/s interface after the evaporation of solvent. Moreover, by increasing the chain length of the alkylated acids, the weight of the carboxylic group, also being the group responsible for the dielectric properties, diminished from heptanoic to nonanoic acid, which could make the easier/earlier appearance of a linear coadsorption effect. However, this was not the case for nonpolar 1-phenyloctane and n-tetradecane: no concentration effect was detected. It showed a strong tendency to aggregate to generate coexistence of separate domains of different phases due to the fast nucleation sites. Furthermore, thermodynamic calculations indicated that the stable structural coexistence of the fluorenone derivative was attributed to synergistic intermolecular dipole–dipole and van der Waals (vdWs) forces at l/s interface. It is believed that the results are of significance to the fields of solvent induced polymorphism assembly and surface science.

D-A-D-type orange-light emitting thermally activated delayed fluorescence (TADF) materials based on a fluorenone unit: simulation, photoluminescence and electroluminescence studies.

Abstract: The design of orange-light emitting, thermally activated, delayed fluorescence (TADF) materials is necessary and important for the development and application of organic light-emitting diodes (OLEDs). Herein, two donor-acceptor-donor (D-A-D)-type orange TADF materials based on fluorenone and acridine, namely 2,7-bis(9,9-dimethylacridin-10(9H)-yl)-9H-fluoren-9-one (27DACRFT, 1) and 3,6-bis(9,9-dimethylacridin-10(9H)-yl)-9H-fluoren-9-one (36DACRFT, 2), were successfully synthetized and characterized. The studies on their structure-property relationship show that the different configurations have a serious effect on the photoluminescence and electroluminescence performance according to the change in singlet-triplet splitting energy (ΔEST) and excited state geometry. This indicates that a better configuration design can reduce internal conversion and improve triplet exciton utilization of TADF materials. Importantly, OLEDs based on 2 exhibited a maximum external quantum efficiency of 8.9%, which is higher than the theoretical efficiency of the OLEDs based on conventional fluorescent materials.

Single-molecule studies of a model fluorenone.

Abstract: Single-molecule fluorescence measurements of 2,7-bis(3,4,5-tri-methoxyphenylethenyl)fluorenone (OFOPV) reveal narrow emission spectra concentrated around 540 nm, with weak emission at longer wavelengths. The wide scattering of emission-maximum wavelengths is attributed to varying molecular environments, with dimers or higher-order aggregates contributing to the low-energy emission. This spectral distribution indicates that emission from monomers of this model fluorenone is mostly green, which is consistent with contaminant emission (g-bands) often observed in fluorene- and polyfluorene-based organic light emitting diode (OLED) devices. A histogram of center wavelengths from 118 single-molecule spectra shows good agreement with the green emission previously observed in thermally stressed 2,7-bis(3,4,5-trimethoxyphenylethenyl)-9,9-diethylfluorene (OFPV). Whereas bulk OFPV exhibits blue fluorescence at about 480 nm, OFOPV bulk thin film measurements reveal red luminescence shifted to 630 nm. This unexpected peak position for bulk OFOPV shifts to higher energies (ca. 540 nm) upon dilution in a solid-state matrix, suggesting that the bulk red emission finds its origins in interactions between fluorenone molecules. Explanations for this red emission include aggregate or excimer formation or intermolecular energy transfer between fluorenone molecules.