The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

Mechanism of the Anthracene-Transfer in a Topochemically Controlled Regiospecific Antipodal C60 Difunctionalization

Ever since the discovery of fullerenes, their mono- and multi-functionalization by exohedral addition chemistry has been a fundamental topic. A few years ago, a topochemically controlled regiospecific di-functionalization of C60 fullerene by anthracene in the solid state was discovered. In the present work, we analyze the mechanism of this unique reaction, where an anthracene molecule is transferred from one C60 mono-adduct to another one under exclusive formation of equal amounts of C60 and of the difficult to make, highly useful, antipodal C60 bis-adduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates only partially from one fullerene when already undergoing bonding interactions with a neighboring fullerene molecule, facilitating the reaction kinetically. Hence, the anthracene transfer occurs via a stabilized intermediate, in which a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong “double-decker” type π-π stacking interactions with both of these fullerenes. Analysis with the distortion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distortion. This analysis sheds light on the existence of simultaneous noncovalent interactions engaging both of the two faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented ‘inverted sandwich’ structure.

Bis-anthracene derived bis-pyridine: selective fluorescence sensing of Al3+ ions

A novel bis-anthracene molecule linked to bis-pyridine by xylylene dibromide (APC) was synthesized as a potent sensor for the detection of Al3+ ions.

A 2:1 co-crystal of 3,5-dibromo-4-cyanobenzoic acid and anthracene

The title co-crystal, C8H3Br2NO2·0.5C14H10, was self-assembled from a 2:1 mixture of the components in slowly evaporating dichloromethane. The molecules adopt a sheet structure parallel to (1-12) in which carboxy hydrogen-bonded dimers and anthracene molecules stagger in both dimensions. Within the sheets, six individual cyano acid molecules surround each anthracene molecule. Cyano acid molecules form one of the two possibleR22(10) rings between neighboring cyano and bromo groups. Compared to the dichloro analog [Britton (2012).J. Chem. Crystallogr.42, 851–855], the dihedral angle between the best-fit planes of acid and anthracene molecules has decreased from 7.1 to 0.9 (2)°.

Proliferating conduction by isomerism

The electrical conduction of isomers of anthracene molecule attached between two semi-infinite gold electrodes was simulated using extended Huckel theory (EHT)-based on semi-empirical model in this research work. The electron transport parameters were examined in two epochs by buffering anthracene and its isomer phenanthrene alternatively between gold electrodes using sulphur as an alligator clip, under variegated bias voltages. Differential NDR effect was observed in both the cases but phenanthrene exhibited more linear I–V curve than its counterpart, anthracene. The simulated results discovered phenanthrene as a better candidate than anthracene towards contributing to electrical conduction in molecular junctions. Phenanthrene reported maximum conductance of 0.74G0 whereas anthracene exhibited 0.03[Formula: see text]G0 at 0.8[Formula: see text]V.

Homoleptic 2,2′-bipyridine metalates(–I) of iron and cobalt, one cocrystallized with an anthracene radical anion and the other with neutral anthracene

Homoleptic 2,2′-bipyridine (bipy) metalates of iron and cobalt have been synthesized directly from the corresponding homoleptic anthracene metalates. In the iron structure, bis[([2.2.2]cryptand)potassium(I)] tris(2,2′-bipyridine)ferrate(–I) anthracene(–I), [K(C18H36N2O6)]2[Fe(C10H8N2)3](C14H10), the asymmetric unit contains one potassium complex cation in a general position, the Fe center and one and a half bipy ligands of the ferrate complex on a crystallographic twofold axis that includes the Fe atom, and one half of an anthracene radical anion whose other half is generated by a crystallographic inversion center. The cations and anions are well separated and the geometry about the Fe center is essentially octahedral. In the cobalt structure, ([2.2.2]cryptand)potassium(I) bis(2,2′-bipyridine)cobaltate(–I) anthracene hemisolvate tetrahydrofuran (THF) disolvate, [K(C18H36N2O6)][Co(C10H8N2)2]·0.5C14H10·2C4H8O, the asymmetric unit contains the cation, anion, and both cocrystallized THF solvent molecules in general positions, and one half of a cocrystallized anthracene molecule whose other half is generated by a crystallographic inversion center. The cation and anion are well separated and the ligand planes in the cobaltate anion are periplanar. Each anthracene molecule is midway between and is oriented perpendicular to a pair of symmetry-related bipy ligands such that aromatic donor–acceptor interactions may play a role in the packing arrangement. The lengths of the bonds that connect the bipy rings support the assertion that the ligands are bipy radical anions in the iron structure. However, in the case of cobalt, these lengths are between the known ranges for a bipy radical anion and a bipy dianion, and therefore no conclusion can be made from the crystallography alone. One cocrystallized THF solvent molecule in the cobalt structure was modeled as disordered over three positions with appropriate geometric and thermal restraints, which resulted in a refined component mass ratio of 0.412 (4):0.387 (3):0.201 (3).

CHARGE STABILITY AND CONDUCTANCE ANALYSIS OF ANTHRACENE-BASED SINGLE ELECTRON TRANSISTOR

The present paper discusses the investigation of electronic properties of anthracene-based single electron transistor (SET) operating in coulomb blockade region using Density Functional Theory (DFT) based Atomistix toolkit-Virtual nanolab. The charging energies of anthracene molecule in isolated as well as electrostatic SET environments have been calculated for analyzing the stability of the molecule for different charge states. Study also includes the analysis of SET conductance dependence on source/drain and gate potentials in reference to the charge stability diagram. Our computed charging energies for anthracene in isolated environment are in good agreement with the experimental values and the proposed anthracene SET shows good switching properties in comparison to other acene series SETs.