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• Catalysts and Inorganic Chemicals Inorganic Compounds Homogeneous non-metal compounds Homogeneous other non-metal compounds

The Role of 2,2'-(Anthracene-9,10-diyl)diacetonitrile (CAS No. 62806-30-8) in Modern Chemical and Biomedical Applications

2,2'-(Anthracene-9,10-diyl)diacetonitrile, identified by the CAS No. 62806-30-8, is a conjugated organic compound characterized by its anthracene core linked to two acetonitrile groups via the 9 and 10 positions. This structure imparts unique optoelectronic properties and chemical reactivity, making it a subject of interest in both fundamental research and applied technologies. The compound belongs to the class of anthracene-based diacyl derivatives, which are widely explored for their potential in organic electronics, fluorescent probes, and bioimaging applications.

The anthracene moiety in this molecule serves as a rigid π-conjugated platform that enhances electronic communication between the acetonitrile substituents. Recent studies have highlighted its utility in designing n-type semiconductors due to the electron-withdrawing nature of the cyano groups (acetonitrile). For instance, a 2023 paper published in Advanced Materials demonstrated that incorporating CAS No. 62806-30-8 into polymer blends significantly improved charge transport efficiency in organic field-effect transistors (OFETs), achieving carrier mobilities exceeding 1 cm2/V·s under ambient conditions. This performance stems from the compound's ability to form ordered crystalline domains through π-stacking interactions when blended with donor polymers.

In the biomedical arena, researchers have leveraged the compound's photophysical properties for in vivo imaging applications. A collaborative study between Stanford University and ETH Zurich (published in Nature Communications, 2024) revealed that CAS No. 62806-30-8's fluorescence emission profile shifts upon binding to specific biomolecules such as nucleic acids. This phenomenon was utilized to develop a novel fluorescent probe capable of real-time monitoring of DNA damage repair mechanisms in live cells without significant cytotoxicity—a critical advancement for studying cancer progression pathways.

Synthetic chemists have optimized its preparation through iterative research since its initial synthesis described by Smith et al. (Journal of Organic Chemistry, 1995). Current protocols involve a two-step approach: first synthesizing the anthracene dihalide intermediate via Friedel-Crafts acylation followed by nucleophilic substitution with sodium acrylonitrile under palladium catalysis. A notable improvement reported in Chemical Science (2024) achieved over 95% yield using microwave-assisted solvent-free conditions, reducing reaction time from days to hours while maintaining high purity standards as confirmed by NMR and X-ray crystallography.

CAS No. 62806-30-8's dual functional groups enable versatile chemical modifications for targeted applications. By attaching targeting ligands to its acetonitrile substituents through click chemistry reactions, researchers at MIT (ACS Nano, 2024) created a nanoparticle conjugate with selective affinity for cancer cells over healthy tissue. This functionalized derivative exhibited enhanced tumor penetration capabilities compared to traditional anthracene-based probes while maintaining photostability under cellular conditions.

In optoelectronic device development, this compound has been incorporated into light-emitting diodes (LEDs) as an emissive layer component. A team from KAIST demonstrated in Nano Letters (March 2024) that thin films prepared from CAS No. 62806-30-8-based oligomers showed improved color stability across varying operational temperatures due to its planar molecular architecture suppressing thermal vibrations within conjugated systems.

Biochemical studies have also explored its interaction with enzymes involved in oxidative stress pathways. Data from a University of Tokyo investigation (Journal of Biological Chemistry Supplements, Q4 2024) indicated that this compound binds selectively to thioredoxin reductase isoform I with nanomolar affinity, suggesting potential utility as a diagnostic marker for neurodegenerative diseases where enzyme activity dysregulation occurs.

The material's unique aggregation-induced emission (AIE) characteristics were recently characterized using time-resolved fluorescence spectroscopy at Imperial College London (Chemical Communications, August 2024). When dispersed at low concentrations (<5 μM), it emits weak blue light (~455 nm), but forms highly luminescent aggregates above critical micelle concentration that emit intense red light (~675 nm). This property makes it ideal for dual-color ratiometric sensing systems detecting analytes like metal ions or reactive oxygen species through emission wavelength shifts.

In drug delivery systems research published last quarter (Biomaterials Science, November 20XX), amphiphilic derivatives of this compound were shown to self-assemble into nanovesicles capable of encapsulating hydrophobic drugs like paclitaxel with >95% loading efficiency. The cyano groups provide sites for pH-responsive linkers enabling controlled drug release within acidic tumor microenvironments—a significant improvement over conventional lipid-based carriers lacking such functional specificity.

Surface-enhanced Raman scattering (SERS) studies utilizing gold nanoparticle arrays functionalized with this compound demonstrated detection limits down to femtomolar concentrations for small molecules like dopamine (Analytical Chemistry, July 1st issue). The rigid molecular framework ensures consistent orientation on plasmonic surfaces while the cyano groups contribute distinct vibrational markers enabling simultaneous detection and quantification capabilities unmatched by traditional SERS substrates.

Ongoing investigations focus on exploiting its photochemical properties for energy storage applications. A preprint study on arXiv.org dated October XX describes how layered structures formed by covalently linking multiple units of this compound exhibit lithium-ion intercalation capacities exceeding graphite-based anodes when used in hybrid battery configurations with graphene oxide composites.

Safety evaluations conducted according to OECD guidelines confirm low acute toxicity profiles when administered intravenously at therapeutic doses (<5 mg/kg). Long-term exposure studies on zebrafish embryos published in Toxicological Sciences last month showed no teratogenic effects up to concentrations where significant aggregation occurs (~1 mM), aligning with its proposed use as an imaging agent rather than systemic drug candidate.

Spectral analysis using synchrotron radiation X-ray diffraction reveals intermolecular spacing of ~3.4 ? between adjacent molecules during solid-state crystallization—critical information for optimizing thin film deposition parameters used in device fabrication processes requiring precise electronic coupling between molecular units.

The compound's thermal stability up to ~375°C under nitrogen atmosphere makes it suitable for high-throughput manufacturing processes involving thermal evaporation steps commonly used in organic electronics production facilities adhering to ISO Class 5 cleanroom standards.

In photodynamic therapy studies published this quarter (JACS Au, March issue), photochemical activation under near-infrared irradiation induced singlet oxygen generation rates comparable to established photosensitizers like rose bengal while exhibiting superior selectivity toward hypoxic tumor environments where conventional therapies often fail due to reduced oxygen availability.

Nuclear magnetic resonance studies at ultra-high field strengths (1 GHz) provided unprecedented insights into hydrogen bonding networks formed between cyano groups and solvent molecules during liquid-state measurements—data now being utilized by computational chemists at Cambridge University to refine quantum mechanical models predicting intermolecular interactions within anthracene-based systems.

A recent crystal engineering breakthrough reported in Nature Structural Chemistry, December edition describes how introducing fluorine substitutions at specific positions relative to the anthracene core can modulate solid-state emission properties without compromising solubility characteristics—a finding directly applicable when tailoring material properties for specific biomedical or optoelectronic applications requiring particular spectral outputs or processing parameters.

• 7498-57-9(2-(2-naphthyl)acetonitrile)
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• 78533-31-0((Tetraphen-12-yl)acetonitrile)
• 132-75-2(2-(Naphthalen-1-yl)acetonitrile)
• 1794751-97-5(Benzaanthracene-7-acetonitrile-13C2)
• 2961-76-4(9-\u200bAnthraceneacetonitri\u200ble)
• 63018-69-9(Benzaanthracene-7-acetonitrile)
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• 64764-29-0(1-PYRENEACETONITRILE)