Zbigniew Marcinow

‘Buckybowls’—introducing curvature by solution phase synthesis

Abstract New, non-pyrolytic methods are presented for the synthesis of curved-surface, polynuclear aromatic hydrocarbons related to the fullerenes. Tetrabromocorannulene is conveniently prepared on a large scale and then converted to corannulene, and also used as a synthon for further elaboration.

Chemistry on the rim of buckybowls: derivatization of 1,2,5,6-tetrabromocorannulene

Abstract Synthesis of a number of substituted corannulenes and dibenzo[ a , g ]corannulenes starting from 1,2,5,6-tetrabromocorannulene 3 is described. Since 3 is conveniently obtained by a large scale, non-pyrolytic route, it may serve as a synthon for the further elaboration of this bowl-shaped system.

Concerning the structure of the corannulene tetraanion.

Abstract The question of an anion within an anion structure for corannulane tetraanion is examined by ab initio and semi-empirical calculations, as well as by the behavior of corannulene anionic intermediates in anhydrous ammonia. Calculations do not lend much support to a central cyclopentadienyl anion in the tetraanion, and a tetraanion is either not formed or does not resist protonation in liquid ammonia.

BENZENESELENINIC ANHYDRIDE OXIDATION OF 1,2-DIARYLETHANES AND 1,2-DIARYLETHYLENES TO 1,2-DIARYLDIKETONES

Abstract 1,2-Diarylethanes and 1,2-diarylethylenes can be oxidized directly to 1,2-diaryldiketones in good yields by reaction with benzeneseleninic anyhdride (BSA) at 120 °C in chlorobenzene.

1,2,5,6-Tetraketopyracene : synthesis, and structure by ab initio calculation and X-ray analysis

Abstract The title compound is conveniently synthesized from the known 1,2-diketopyracene via NBS bromination followed by reaction with silver nitrate in acetonitrile, and treatment with sodium acetate trihydrate in DMSO. Its structure determined by semiempirical PM3 and ab initio calculations is in excellent agreement with the x-ray analysis, and suggests that the bond alternation observed in pyracylene and related compounds is probably not due to antiaromaticity.

Bowl stacking in curved polynuclear aromatic hydrocarbons: crystal and molecular structure of cyclopentacorannulene

Cyclopentacorannulene (dibenzo[ghi,mno]cyclopenta[cd]fluoranthene) exhibits long-range concave–convex bowl stacking in the crystal; its molecular structure is satisfactorily described by ab initio calculations at both HF/3-21G and HF/6-31G* levels.

The first crystal structure characterization of a semibuckminsterfullerene, and a novel synthetic route

Tetrabromosemibuckminsterfullerene 6, obtained by a novel synthetic route, is converted to the tetramethyl derivative 7; X-ray crystal structure determination of the latter reveals a highly nonplanar, bowl-shaped molecule with solvating CCl4 molecules separating the hydrocarbon moieties.