Hexa-(2-ethylhexyl)-hexa-peri-hexabenzocoronene as archetypal model compound of asphaltenes and MAONs

Hexa(ethylhexyl)-hexa-(peri)-hexabenzocoronene (HEH-HBC) was selected as model compound of asphaltenes. In fact, in the “island” model the asphaltenes are described with a relatively large aromatic core surrounded by aliphatic chains attached to the edges of the core. In their turn the asphaltenes are considered model compounds of MAONs (Mixed Aromatic-aliphatic Organic Nanoparticles), the possible carriers of the Unidentified Infrared Bands (UIBs), i.e. a set of certain infrared features found in very different astrophysical objects. The differential scanning calorimetric analysis (DSC) shows that HEH-HBC displays a discotic liquid crystal behavior, similar to that observed also in a selected authentic petroleum asphaltene sample. The electronic absorption spectrum of HEH-HBC was recorded for the first time in hydrocarbon solvents fully transparent in the UV, permitting to observe the UV part of HEH-HBC and to compare it with that of unsubstituted HBC. The FT-IR spectrum of HEH-HBC was recorded not only at room temperature but also at higher resolution at the liquid nitrogen temperature. The molar extinction coefficients and integrated molar absorptivity of the main bands were also estimated. The results are briefly discussed from an astrochemical perspective.