42824-53-3

Usage

Uses

Used in Organic Synthesis:
9,10-Di(p-carboxyphenyl)anthracene is utilized as a key intermediate in the synthesis of various organic compounds due to its structural features and reactivity, contributing to the development of new chemical entities with specific properties.
Used in Materials Science:
In the field of materials science, 9,10-Di(p-carboxyphenyl)anthracene is employed as a component in the creation of novel materials, leveraging its thermal stability and other physical-chemical attributes to enhance material performance.
Used in Biological Research as a Fluorescent Probe:
9,10-Di(p-carboxyphenyl)anthracene is used as a fluorescent probe in biological studies, allowing researchers to track and visualize specific biological processes or interactions within complex systems due to its fluorescent properties.
Used in Organic Electronic Devices:
9,10-Di(p-carboxyphenyl)anthracene is applied in the development of organic electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs), where its光电特性 contribute to improved device performance and efficiency.
Each of these applications takes advantage of the unique characteristics of 9,10-Di(p-carboxyphenyl)anthracene, highlighting its versatility and potential impact across different scientific and industrial domains.

Upstream product

• 24672-72-8 9,10‐bis(4‐bromophenyl)anthracene 
• 1156005-02-5 dimethyl-4,4′-(anthracene-9,10-diyl)-dibenzoate 
• 523-27-3 9,10-Dibromoanthracene 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 14047-29-1 4-carboxyphenylboronic acid 
• 55517-98-1 9,10-bis-(4-bromo-phenyl)-9,10-dihydro-anthracene-9,10-diol 

Relevant academic research and scientific papers

Unprecedented Ultralow Detection Limit of Amines using a Thiadiazole-Functionalized Zr(IV)-Based Metal-Organic Framework

A luminescent Zr(IV)-based metal-organic framework (MOF), with the underlying fcu topology, encompassing a ?-conjugated organic ligand with a thiadiazole functionality, exhibits an unprecedented low detection limit of 66 nM for amines in aqueous solution.

Engineering COFs as smart triggers for rapid capture and controlled release of singlet oxygen

Capture and controlled release of singlet oxygen (1O2) are of great significance but very challenging due to its very short lifetime and high reactivity. To address this challenge, we rationally designed and fabricated a highly crystalline, robust, and porous three-dimensional covalent organic framework (3D COF) by installing functional anthracene moieties on its skeleton for1O2related applications. Attributed to its open networks, regular channels, and light skeletal density, the active anthracene sites in the 3D COF can be easily and fully accessed, hence affording superior performance compared with other materials such as 2-dimensional COFs and amorphous polymers. Notably, the 3D COF displays the current record-high1O2capture rate among all reported porous materials, verified by various characterization techniques and rational analysis. Furthermore, we used the 3D COF platform as a stimuli-responsive smart material for anti-fake applications. This study not only provides an outstanding platform for1O2capture and release but also extends the application scope of COFs.

A dendritic DPA annihilator—syntheses, photophysical properties and application for co-assembling enhanced triplet-triplet annihilation upconversion

A dendritic annihilator D-2 containing 18 peripherical methyl ester units was synthesized by attaching the branches on the phenyl unit of 9,10-diphenylanthracene (DPA). The absorption and emission spectra of D-2 are very similar to the unbranched DPA diacid 5 and the lower branched homolog D-1, while the fluorescence quantum yield increased with the degrees of the branching and was determined to be 86.9percent for D-2 in MeOH. D-2 was used as the annihilator for triplet-triplet annihilation upconversion with a Schiff-base Pt(II) complex serving as the sensitizer. It was found that D-2 showed very weak UC emission in MeOH with a UC quantum yield of only 1.4percent. Interestingly, the UC emission intensity increased significantly by adding different amounts of water in MeOH, the UC intensity was enhanced by more than 9 fold by adding 40percent water into MeOH, and the UC quantum yield was determined to be 10.2percent in MeOH with 40percent water. A mechanism for the enhancing of UC emission was proposed: When in MeOH, the large molecule size of the dendrimer limited the movability of the acceptor, and the shielding effect of the dendritic branches on the DPA core limited the intimate contacts among DPA cores or between DPA core and the sensitizer. When the water was added, D-2 aggregated to nanoparticles with internal hydrophobic cavities induced by the hydrophobic effect and π-π stacking of DPA core, the sensitizer Pt-1 was captured in the internal hydrophobic cavities, and thus, both the TTET and TTA processes were greatly accelerated which attributed to the enhanced TTA-UC.

Stepwise Assembly of Turn-on Fluorescence Sensors in Multicomponent Metal–Organic Frameworks for in Vitro Cyanide Detection

The controlled synthesis of multicomponent metal–organic frameworks (MOFs) allows for the precise placement of multiple cooperative functional groups within a framework, leading to emergent synergistic effects. Herein, we demonstrate that turn-on fluorescence sensors can be assembled by combining a fluorophore and a recognition moiety within a complex cavity of a multicomponent MOF. An anthracene-based fluorescent linker and a hemicyanine-containing CN?-responsive linker were sequentially installed into the lattice of PCN-700. The selective binding of CN? to hemicyanine inhibited the energy transfer between the two moieties, resulting in a fluorescence turn-on effect. Taking advantage of the high tunability of the MOF platform, the ratio between anthracene and the hemicyanine moiety could be fine-tuned in order to maximize the sensitivity of the overall framework. The optimized MOF-sensor had a CN?-detection limit of 0.05 μm, which is much lower than traditional CN? fluorescent sensors (about 0.2 μm).

Charge Transfer from Upconverting Nanocrystals to Semiconducting Electrodes: Optimizing Thermodynamic Outputs by Electronic Energy Transfer

Light-harvesting inorganic nanocrystals play an important role in emerging solar energy conversion and optoelectronic devices. We describe here a strategy for a new family of photoelectrodes with upconverting nanocrystal assemblies as the photosensitizer. The assemblies consist of oleic acid-capped cadmium selenide (CdSe) nanocrystals that coordinate directly onto a layer of surface-bound, carboxylic acid-derivatized anthracenes through displacement of the oleic acid capping ligands. Steady-state emission and transient absorption measurements show that the upconverting nanocrystal assemblies, selectively excited by green light, generate singlet excitons that enable efficient charge injection into both the conduction band of TiO2 at the photoanode and the valence band of NiO at the photocathode. The singlet excitons form by sensitized triplet-triplet annihilation within the compact layer of anthracenes on the electrode surfaces. Density of state analysis reveals that the electronic coupling between the anthracene singlet excited states and the oxides provides a thermodynamic basis for light-induced charge transfer. The interplay between the excited-state populations at the surface-bound molecules and the assembled nanocrystals presents new design rules that can potentially overcome the limitations of previous dye-sensitized photoelectrochemical cells for catalytic applications.

Assembly-enhanced triplet-triplet annihilation upconversion in the aggregation formed by Schiff-base Pt(II) complex grafting-permethyl-β-CD and 9, 10-diphenylanthracence dimer

Water-soluble triplet sensitizer with permethyl-β-cyclodextrin (PMCD) grafting on a Schiff-base Pt(II) complex (Pt-2), in which PMCD unit serves as a host for binding the acceptors and the Schiff-base Pt(II) complex serves as a triplet sensitizer, was syn

Structural Transformation in Metal–Organic Frameworks for Reversible Binding of Oxygen

Polycyclic aromatic derivatives can trap 1O2 to form endoperoxides (EPOs) for O2 storage and as sources of reactive oxygen species. However, these materials suffer from structural amorphism, which limit both practical applications and fundamental studies on their structural optimization for O2 capture and release. Metal–organic frameworks (MOFs) offer advantages in O2 binding, such as clear structure–performance relationships and precise controllability. Herein, we report the reversible binding of O2 is realized via the chemical transformation between anthracene-based and the corresponding EPO-based MOF. It is shown that anthracene-based MOF, the framework featuring linkers with polycyclic aromatic structure, can rapidly trap 1O2 to form EPOs and can be restored upon UV irradiation or heating to release O2. Furthermore, we confirm that photosensitizer-incorporated anthracene-based MOF are promising candidates for reversible O2 carriers controlled by switching Vis/UV irradiation.

Supramolecular Assembly-Improved Triplet–Triplet Annihilation Upconversion in Aqueous Solution

Water-soluble 9,10-diphenylanthracene-modified γ-cyclodextrin derivatives A1 and A2, in which the γ-cyclodextrin unit serves as a molecular host for a binding sensitizer, and the 9,10-diphenylanthracene moiety plays a role as an emitter/annihilator, were synthesized to investigate the supramolecular triplet–triplet annihilation (TTA) upconversion in aqueous solution. Both A1 and A2 readily aggregate and form nanoscale assemblies in water as a combined result of host–guest complexation and π–π stacking among the 9,10-diphenylanthracenes. The aggregation behavior of the supramolecular emitters was fully characterized by using a diversity of methods, including dynamic light scattering (DLS), SEM, NMR, fluorescence, and circular dichroism studies. Fluorescence spectroscopic analysis reveals that the emitters have high fluorescence quantum yields in water (82 and 90 % for A1 and A2, respectively), thus demonstrating that aggregation does not quench the fluorescence. By using a coordinated ruthenium sensitizer, a high TTA upconversion quantum yield of up to 6.9 % was observed for this supramolecular TTA system, which is significantly higher than the value (0.5 %) obtained with nonassembled emitters in organic solvent and in contrast to the fact that TTA upconversion emission in aqueous solution is usually low or negligible. We ascribe the strong TTA upconversion emission in the present supramolecular assembly system to an efficient TTA process, which is facilitated along the stacked emitters by triplet energy migration and improved triplet–triplet energy transfer through host–guest complexation.

One-dimensional networks formed via the self-assembly of anthracenedibenzoic acid with zinc(II)

Self-assembly of metal–organic coordination polymers occurs because of enthalpically favorable interactions. In the case of the bulky 4,4′-(anthracene-9,10-diyl)dibenzoic acid ligand (abdH2), we demonstrate that the presence of numerous π–π and

3D Long-Range Triplet Migration in a Water-Stable Metal-Organic Framework for Upconversion-Based Ultralow-Power in Vivo Imaging

Triplet-triplet annihilation upconversion (TTA-UC) has gained increasing attention because it allows for harvesting of low-energy photons in the solar spectrum with high efficiency in relevant applications including solar cells and bioimaging. However, the utilization of conventional TTA-UC systems for low-power bioapplications is significantly hampered by their general incompatibility and low efficiency in aqueous media. Herein we report a metal-organic framework (MOF) as a biocompatible nanoplatform for TTA-UC to realize low-power in vivo imaging. Our MOF consists of a porphyrinic sensitizer in an anthracene-based Zr-MOF as a TTA-UC platform. In particular, closely aligned chromophores in the MOF facilitate a long-range 3D triplet diffusion of 1.6 μm allowing efficient energy migration in water. The tunable ratio between sensitizer and annihilator by our synthetic method also allows an optimization of the system for maximized TTA-UC efficiency in water at a very low excitation power density. Consequently, the low-power imaging of lymph node in a live mouse was successfully demonstrated with an excellent signal-to-noise ratio (SNR > 30 at 5 mW cm-2).