ABSTRACT
In a polymer analogous approach, large dendritic oligophenylenes containing benzene and tetraphenylmethane cores are transformed via oxidative cyclodehydrogenation to novel propeller-shaped molecules with large polycyclic aromatic hydrocarbon units as "blades". Structure analysis is performed by a combination of MALDI-TOF mass spectrometry, UV/vis, fluorescence, and Raman spectroscopy using solid-state sample preparation methods. These methods are also utilized to determine the degree of the cyclodehydrogenation reaction.
ABSTRACT
A mild pyrolytic method is proposed for the generation of different carbon micro- and nanoparticles that are either unprecedented or have never been reported under the present experimental conditions. A hexa-alkyl-substituted hexa-peri-hexabenzocoronene serves as a graphite-like starting compound that melts into a discotic liquid crystalline phase prior to heat-induced cross-linking and dehydrogenation. An essential feature of the process is that the liquid crystalline order persists even above 400 degrees C, i.e., during alkyl chain cleavage. The present approach bears a resemblance to carbomesophase formation during graphitization starting from pitch. The pyrolysis products are characterized by matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry, optical microscopy, selected area electron diffraction (SAED), scanning electron microscopy (SEM), and high-resolution transmission electron microscopy (HRTEM).