7218-35-1

Usage

Physical state

Solid

Color

Colorless to pale yellow

Crystal form

Crystals

Solubility

Soluble in organic solvents

Uses

a. Precursor in the synthesis of dyes and pigments
b. Production of pharmaceuticals
c. Production of photovoltaic materials

Importance

Important building block in the chemical industry for creating a wide range of products

Structure

Unique structure and reactivity

Therapeutic applications

Studied for potential use in the treatment of cancer and other diseases

Upstream product

• 635-12-1 1,4-anthraquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 36831-84-2 2,3-dihydro-anthracene-1,4-dione 
• 123-91-1 1,4-dioxane 
• 24301-50-6 anthracene-1,4-diacetate 

Downstream Products

• 13076-29-4 1,4-dimethoxyanthracene 
• 24301-50-6 anthracene-1,4-diacetate 
• 74751-38-5 Methyl-(4-hydroxy-anthryl-⁽¹⁾)-aether 
• 914922-86-4 tetraceno[2,3-b]thiophene-5,12-dione 

Relevant academic research and scientific papers

Functionalized higher acenes: Hexacene and heptacene

We have extended our functionalization strategy for pentacene to the higher acenes hexacene and heptacene. Provided a large enough alkyne substituent is used, these large aromatic rods are both stable and soluble and can be characterized spectroscopically as well as by single-crystal X-ray diffraction. Copyright

Development and mechanistic studies of an optimized receptor for trimethyllysine using iterative redesign by dynamic combinatorial chemistry

A new small molecule receptor, A2N, has been identified that binds specifically to trimethyllysine (Kme3) with sub-micromolar affinity. This receptor was discovered through the iterative redesign of a monomer known to incorporate through dynamic combinatorial chemistry (DCC) into a previously reported receptor for Kme3, A2B. In place of monomer B, the newly designed monomer N introduces an additional cation-π interaction into the binding pocket, resulting in more favorable binding to Kme3 by 1.3 kcal mol-1, amounting to a 10-fold improvement in affinity and a 5-fold improvement in selectivity over Kme2. This receptor exhibits the tightest affinity and greatest selectivity for KMe 3-containing peptides reported to date. Comparative studies of A 2B and A2N provide mechanistic insight into the driving force for both the higher affinity and higher selectivity of A2N, indicating that the binding of KMe3 to A2N is both enthalpically and entropically more favorable. This work demonstrates the ability of iterative redesign coupled with DCC to develop novel selective receptors with the necessary affinity and selectivity required for biological applications. This journal is the Partner Organisations 2014.

Acyclic Cucurbit[n]uril-Type Receptors: Aromatic Wall Extension Enhances Binding Affinity, Delivers Helical Chirality, and Enables Fluorescence Sensing

We report the linear extension from M1 to M2 to anthracene walled M3 which adopts a helical conformation (X-ray) to avoid unfavorable interactions between sidewalls. M3 is water soluble (=30 mm) and displays enhanced optical properties (?=1.28×105 m?1 cm?1, λmax=370 nm) relative to M2. The binding properties of M3 toward guests 1–29 were examined by 1H NMR and ITC. The M3?guest complexes are stronger than the analogous complexes of M2 and M1. The enhanced binding of M3 toward neuromuscular blockers 25, 27–29 suggests that M3 holds significant promise as an in vivo reversal agent. The changes in fluorescence observed for M3?guest complexes are a function of the relative orientation of the anthracene sidewalls, guest concentration, Ka, and guest electronics which rendered M3 a superb component of a fluorescence sensing array. The work establishes M3 as a next generation sequestering agent and a versatile component of fluorescence sensors.

Fluorescent molecule for recognizing copper ions, preparation method and application

The invention discloses a fluorescent molecule for recognizing copper ions, a preparation method and application. Polycyclic aromatic hydrocarbons such as naphthalene rings or anthracene rings are used as initial raw materials; through a series of optimized organic synthesis reaction (substitution and addition), after the connection with different recognition sites, molecular clamp body tweezer host compounds with different recognition performance can be obtained. The fluorescent molecule can be used for copper ion detection and solves the problems that the existing molecule device is difficult to effectively recognize object molecules.

Conformational Planarization versus Singlet Fission: Distinct Excited-State Dynamics of Cyclooctatetraene-Fused Acene Dimers

A set of flapping acene dimers fused with an 8π cyclooctatetraene (COT) ring showed distinct excited-state dynamics in solution. While the anthracene dimer showed a fast V-shaped-to-planar conformational change within 10 ps in the lowest excited singlet state, reminding us of extended Baird aromaticity, the tetracene dimer and the pentacene dimer underwent intramolecular singlet fission (SF) in different manners: A fast and reversible SF with a characteristic delayed fluorescence (FL), and a fast and quantitative SF, respectively. Conformational flexibility of the fused COT linkage plays an important role in these ultrafast dynamics, demonstrating the utility of the flapping molecular series as a versatile platform for designing photofunctional systems.

Water-soluble fluorescent polymers that respond to singlet oxygen

Although acenes with more than three fused rings can both fluoresce efficiently and react with singlet oxygen (1O2) rapidly, their hydrophobic nature presents a challenge to their use in aqueous environments. Herein we report a series of fluorescent, water-soluble random copolymers that each comprise (oligoethylene glycol) methacrylate (OEGMA) and one of several diarylacene methacrylates, including a tetracene methacrylate and a tetraceneothiophene methacrylate. Exposure to 1O2 in water oxidizes the pendant acenes, resulting in diminution of their fluorescence intensities. The observed rate of oxidation of the tetracene-containing polymers compares favorably with a commercial 1O2-sensitive dye. Polymers that also include energy-donating coumarin side chains show ratiometric fluorescence changes in response to 1O2.

Syntheses and bioactivities of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones. Unusual reactivities with amines

A number of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones have been synthesized and their anticancer and antimalarial activities evaluated. A one-pot synthesis of 2,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione (4) was achieved by heating a mixture of 1,4-dimethoxyanthracene, methoxyhydroquinone, silver oxide, and zinc iodide in toluene. Regioselective bromination of 4 and 2-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (7) with N-bromosuccinimide provided 2-bromo-3,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]-benzenoanthracene-1,4-dione and 2-bromo-3-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (1), respectively. The reactions of 1 with aliphatic primary amines and secondary amines, respectively, produced different products, a result most likely attributed to the different basicities (or nucleophilicities) and steric effects of the two kinds of amines. The structure of the displacement product, 2-bromo-3- [2-(tert-butoxycarbonyl)ethylamino]-9,10-dihydro-9,10-[1,2] benzenoanthracene-1,4,5,8-tetrone, from the reaction of 1 with tert-butyl 3-aminopropanoate was unequivocally determined by a single-crystal X-ray analysis. IC50 values of triptycene bisquinones for the inhibition of L1210 leukemia cell viability are in the 0.11-0.27 μM range and for the inhibition of Plasmodium falciparum 3D7 are in the 4.7-8.0 μM range.

Triptycene analogs

This invention provides analogs of triptycene which are useful as anticancer drugs, as well as for other uses. The potency of these compounds is in a similar magnitude as daunomycin, a currently used anticancer drug. Each compound of the invention produces one or more desired effects (blocking nucleoside transport, inhibiting nucleic acid or protein syntheses, decreasing the proliferation and viability of cancer cells, inducing DNA fragmentation or retaining their effectiveness against multidrug-resistant tumor cells).

Novel seco cyclopropa[c]pyrrolo[3,2-e]indole bisalkylators bearing a 3,3′-arylenebisacryloyl group as a linker

We synthesized the novel seco cyclopropa[c]pyrrolo[3,2-e]indole (CPI) bisalkylators and evaluated their antitumor activity. Among these derivatives, 11a (AT-760), in which the two seco 3-methoxycarbonyl-2-trifluoromethyl CPI (MCTFCPI) moieties are connected with a 3,3′-(1,4-phenylene)bisacryloyl group, was found to exhibit more potent cytotoxicity and antitumor activity against HeLaS3 human uterine cervix carcinoma cells and Colon 26 adenocarcinoma cells, respectively, than 8 (bizelesin, U-77,779). It also appeared that compound 11a exhibits improved in vivo efficacy in the human colon CX-1 model when compared to either compound 8 or mitomycin C (MMC). Efficacious doses for 11a were found to be 2-fold lower than those for 8.

Photochemical properties of aromatic carbonyl compounds belonging to different spectral luminescence groups of molecular systematics

The photochemical activity in photo-reduction reactions of a series of carbonyl compounds in ethanol and heptane solutions has been studied at room temperature.The quantum yields of the photo-dissociation of the molecules have been determined.The relative positions of the electronic states of different orbital nature and multiplicity have been compared with the efficiency of the photo-conversion and the mechanism of the photo-reaction in the case of 1,4-quinones and aromatic diketones.