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InChI:InChI=1/C16H12O/c1-3-7-13-11(5-1)9-12-6-2-4-8-14(12)16(13)15-10-17-15/h1-9,15H,10H2

Upstream product

• 2444-68-0 9-vinylanthracene 
• 2181-42-2 trimethylsulphonium iodide 
• 642-31-9 9-anthracene aldehyde 

Downstream Products

• 874945-80-9 2-amino-2-(anthracen-9-yl)ethanol 
• 1284240-01-2 4-(anthracen-9-yl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole 

Relevant academic research and scientific papers

New strategies towards reversible and mendable epoxy based materials employing [4πs + 4πs] photocycloaddition and thermal cycloreversion of pendant anthracene groups

The present study highlights the design of reversibly crosslinkable epoxy based materials that undergo well-defined bond formation and bond cleavage in response to external stimuli. In this approach the controlled crosslinking relies on the highly reversible nature of [4πs + 4πs] cycloaddition reactions of anthracene derivatives. New epoxy monomers are synthesized which bear reactive anthracene groups that enable the formation of crosslinked networks due to concerted photocycloaddition reaction. A subsequent heating to temperatures up to 130°C leads to thermally induced cleavage of the photodimers again. The crosslink kinetics as well as the reversible bond formation of the new epoxy based resins are characterized by spectroscopic techniques and dynamic mechanical analysis. Along with the reversible network characteristics, the new epoxy based materials promote intrinsically healable material properties since the photodimers are mechanochemically cleaved upon crack insertion. In fluorescence micrographs the evolution of a strong fluorescence emission along the crack planes is observed which can be related to the regeneration of the original anthracene groups in the damage-zone. Repair of the macroscopic cracks across the restored anthracene groups is achieved upon re-irradiation with UV-light (λ > 300 nm) and simultaneous heating at temperatures which are above the glass transition temperature of the epoxy based materials. The ability of the new materials to restore their mechanical properties after a repeated inflicting of macroscopic cracks at the same fracture point is confirmed by three-point bending tests. Load-displacement curves reveal that in terms of force at break the reversibly crosslinkable networks promote healing efficiencies between 84 and 100% after the first repair step.

Copper based coordination polymers based on metalloligands: Utilization as heterogeneous oxidation catalysts

This work presents the synthesis and characterization of two Cu(ii)-based coordination polymers prepared by utilizing two different Co(iii)-based metalloligands offering appended arylcarboxylic acid groups. Both coordination polymers are three-dimensional in nature and present pores and channels filled with water molecules. Both coordination polymers function as heterogeneous catalysts for the epoxidation of various olefins using O2 while employing isobutyraldehyde as the coreductor and for peroxide-mediated oxidation of assorted benzyl alcohols. The catalytic results illustrate efficient oxidation reactions, whereas the hot-fltration test and leaching experiments indicate the true heterogeneous nature of the catalysis.

Manganese- and cobalt-based coordination networks as promising heterogeneous catalysts for olefin epoxidation reactions

We demonstrate the synthesis of Mn2+- and Co2+-based coordination networks using two Co3+-based metalloligands differing by the position of the appended arylcarboxylate groups. The structural analyses reveal topologically distinct networks with pores of variable dimensions allowing facile diffusion of substrates and/or reagents. All four networks function as heterogeneous catalysts for the olefin epoxidation reactions using tert-butyl-hydroperoxide without any requirement of solvent or additive. Control and optimization experiments illustrate recyclable network-based catalysts that make them attractive candidates for the "greener" oxidation chemistry processes.

Manganese Complexes of Pyrrole- and Indolecarboxamide Ligands: Synthesis, Structure, Electrochemistry, and Applications in Oxidative and Lewis-Acid-Assisted Catalysis

This work shows the synthesis and structural, spectroscopic, and electrochemical properties of MnIII complexes supported with pyrrole- and indolecarboxamide ligands. In all cases, the respective ligand constitutes a N4 coordination sphere about the MnIII ion. The MnIII complexes of pyrrolecarboxamide ligands are square pyramidal with a fifth Cl atom, whereas analogous complexes of indolecarboxamide ligands are essentially square planar. Electrochemical studies reveal highly negative MnIII/II and moderately positive MnIV/III redox potentials. In situ generated Mn4+ species of the pyrrolecarboxamide ligands were characterized by absorption and electron paramagnetic resonance spectroscopy. All complexes functioned as catalysts in olefin epoxidation reactions by using PhIO as the oxo-transfer agent. All complexes also acted as Lewis acid catalysts for ring-opening reactions of assorted epoxides with various nucleophiles. We also show a one-pot, two-step epoxidation reaction followed by ring opening, which illustrates the catalytic significance of the present complexes. Importantly, MnIII complexes carrying electron-donating substituents on the ligand were found to be better catalysts.

Mononuclear complexes of amide-based ligands containing appended functional groups: Role of secondary coordination spheres on catalysis

Amide-based ligands H2L1, H2L2 and H2L3 containing thiazole, thiazoline and benzothiazole appended groups have been used to synthesize Zn2+ (1 and 3), Cd2+ complexes (2 and 4), and a Mn2+ complex (5). In all cases, potentially multidentate ligands create a meridional N3 coordination environment around the M(ii) ion whereas additional sites are occupied by labile nitrate ions in 1-4 and MeOH in 5. Interestingly, metal complexation caused the migration of protons from amidic N-H sites to the appended heterocyclic rings in complexes 1-4. Structural studies show that the protonated heterocyclic rings in these complexes create a hydrogen bond based cavity adjacent to the metal ion. Importantly, binding studies confirm that the substrates are bound within the complex cavity closer to the Lewis acidic metal in all complexes including the oxidation-sensitive Mn ion in complex 5. All complexes have been utilized as the reusable and heterogeneous catalysts for ring-opening reactions of assorted epoxides, cyanation reactions of various aldehydes, and epoxidation reactions of several olefins. This journal is

Determining the enantioselectivity of chiral catalysts by mass spectrometric screening of their racemic forms

The enantioselectivity of a chiral catalyst can be determined from its racemic form by mass spectrometric screening of a nonequal mixture of two mass-labeled quasienantiomeric substrates. The presented method opens up new possibilities for evaluating catalyst structures that are not readily available in enantiomerically pure form.

Catalytic oxidation of alkenes with a surface-bound metalloporphyrin- peptide conjugate

A novel surface-bound metalloporphyrin-peptide conjugate was prepared and used to catalytically oxidize alkenes in the presence of iodosylbenzene. The catalyst was found to oxidize a number of alkene substrates in good yield under a variety of reaction conditions. Comparison to control experiments using surface-bound Mn(III)tetraphenylporphyrin showed differences in oxidation yields and ratios of oxidized products. Substrate competition experiments demonstrated the ability of the conjugate catalyst to discriminate between substrates on the basis of size. Both results suggest oxidative catalysis occurred between the porphyrin ring and the peptide chain with the peptide influencing the outcome of the reaction in accord with the catalyst design.