9,10-Dihydroanthracene is a chemical compound belonging to the polycyclic aromatic hydrocarbon (PAH) family, characterized by its unique fused-ring structure. This molecular entity consists of four aromatic rings arranged in a linear fashion, with the 9 and 10 positions being saturated with two hydrogen atoms, hence its name. This structural feature distinguishes it from other anthracene derivatives, which typically have unsaturated bonds at these positions.
The compound exhibits certain physical and chemical properties that make it intriguing for scientific research and industrial applications. It is typically a solid at room temperature, with a melting point varying depending on its purity and crystalline form. The aromatic nature of its rings allows for various chemical reactions, such as substitutions, additions, and oxidations, making it a versatile building block in synthetic organic chemistry.
In the field of materials science, 9,10-dihydroanthracene and its derivatives have shown potential in the development of luminescent materials due to their ability to emit light under certain conditions. Furthermore, its structure mimics certain biological molecules, making it a useful tool in studying molecular interactions and biological processes.
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| Chemical Formula | C14H12 |
| Exact Mass | 180.09 |
| Molecular Weight | 180.25 |
| m/z | 180.09 (100.0%), 181.10 (15.1%), 182.10 (1.1%) |
| Elemental Analysis | C, 93.29; H, 6.71 |
- Structural and Physical Property Studies: Possessing a molecular formula of C14H12 and a molecular weight of 180.24/180.25. Its specific physical properties, such as a melting point of approximately 111°C (or 104-107°C according to some sources) and a boiling point of 305°C, make it a subject of interest for studies on aromatic hydrocarbons. Researchers often investigate its molecular structure, bonding patterns, and electronic configurations to gain insights into the behavior of similar compounds.
- Reaction Mechanisms: Understanding the reaction mechanisms involving it can contribute to advancements in organic chemistry. Studies on its synthesis, decomposition, and reaction with other compounds can provide valuable information for designing new synthetic pathways and improving existing chemical processes.
- Organic Electronics: Recent research has explored the potential and its derivatives in organic electronics, particularly in organic electroluminescent (EL) materials and organic light-emitting diodes (OLEDs). The luminescent properties of these compounds make them attractive for applications in display technologies and lighting systems.
- Luminescent Devices: Dihydroanthracene derivatives have been reported to exhibit luminescent properties that can be tailored through chemical modifications. This makes them promising candidates for the development of novel luminescent devices with improved efficiency and stability.
- Environmental Impact Assessment: As with any chemical compound, assessing the environmental impact is crucial. Studies on its biodegradability, aquatic toxicity, and persistence in the environment can help determine appropriate disposal methods and regulatory measures to minimize its potential harm to ecosystems.
- Pollutant Detection and Remediation: Given its aromatic structure, it may be present in certain industrial waste streams or environmental contaminants. Research on its detection and removal methods can contribute to the development of effective pollution control strategies.
- Potential Drug Candidates: Although direct applications in pharmaceuticals are limited, its structural similarity to certain bioactive compounds may inspire the design of new drug candidates with desired therapeutic properties.
- Biomedical Research Tools: Modified versions could serve as fluorescent probes or markers in biomedical research, aiding in the visualization and study of biological processes and structures.
- Synthesis of Complex Molecules: Serving as an intermediate in the synthesis of more complex molecules with specific functional groups and properties. Its reactivity and stability make it a suitable starting point for the preparation of a variety of organic compounds.
About Aromatic hydrocarbons
Aromatic hydrocarbons, also known as arenes, constitute a significant class of organic compounds characterized by the presence of one or more aromatic rings in their molecular structures. These rings are typically six-membered carbon rings with a unique electronic configuration that includes delocalized π electrons, contributing to their stability and distinct chemical properties.
Key Features
Aromaticity: The defining feature of aromatic hydrocarbons is their aromaticity, which arises from the cyclic and planar arrangement of carbon atoms with alternating single and double bonds. This configuration allows for the delocalization of π electrons, creating a resonance structure that stabilizes the molecule.
Structure: The simplest aromatic hydrocarbon is benzene (C6H6), which serves as the foundational building block for more complex aromatic compounds. Other aromatic hydrocarbons can include naphthalene (C10H8), anthracene (C14H10), and phenanthrene (C14H10), which contain fused aromatic rings.
Properties: Aromatic hydrocarbons are generally colorless, flammable liquids or solids with distinctive aromas (hence the name). They are relatively stable and resistant to chemical reactions under normal conditions but can undergo substitution, addition, and oxidation reactions under specific conditions.
Occurrence: Naturally, aromatic hydrocarbons are found in coal tar, petroleum, and some essential oils. They are also produced industrially through various synthetic processes, such as catalytic cracking and reforming of hydrocarbons.
Applications: Due to their unique properties, aromatic hydrocarbons have a wide range of applications. Benzene, for instance, is a precursor for numerous chemicals including styrene, phenol, and nylon. Naphthalene is used in the production of phthalic anhydride, which is further used in the manufacture of plastics and dyes. Polycyclic aromatic hydrocarbons (PAHs) are components of asphalt and coal tar, and some have been implicated in environmental pollution and health concerns.
Health and Safety: Many aromatic hydrocarbons are toxic and can pose significant health risks, including carcinogenicity. Exposure to these compounds, particularly through inhalation or ingestion, can lead to adverse health effects. Therefore, proper handling, storage, and disposal practices are crucial to minimize their potential hazards.
Research on 9,10-dihydroanthracene has primarily focused on its cytotoxic properties and potential applications in the medical field.
A notable research case is the study of its cytotoxicity against human cancer cells. Specifically, 9,10-dihydrophenanthrenes, which share structural similarities with it, have been isolated from various natural sources and tested for their anti-proliferative effects on cancer cells. These compounds have demonstrated significant cytotoxic activity against HepG2 cells by arresting the cell cycle at the G2/M phase. This mechanism of action suggests their potential use as anticancer agents.
In terms of future prospects, it and related compounds may pave the way for new therapeutic strategies in cancer treatment. Their cytotoxic properties make them attractive candidates for further development as anticancer drugs. Additionally, with the increasing emphasis on drug repurposing, researchers may explore the possibility of repurposing existing drugs that contain 9,10-dihydroanthracene-like structures for new medical applications.
Furthermore, as the understanding of the molecular mechanisms of aging and chronic diseases progresses, it and its derivatives may also find applications in anti-aging therapies and the treatment of other diseases. However, further research is needed to fully elucidate the biological activities and mechanisms of action of these compounds, as well as to optimize their therapeutic potential.
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