Chen, Qiang; Baumgarten, Martin; Wagner, Manfred; Hu, Yunbin; Hou, Ian Cheng-Yi; Narita, Akimitsu; Muellen, Klaus published the artcile< Dicyclopentaannelated Hexa-peri-hexabenzocoronenes with a Singlet Biradical Ground State>, Related Products of 576-83-0, the main research area is dicyclopentaannelated hexa peri hexabenzocoronene preparation singlet biradical ground state; hexabenzocoronene low bandgap optical electrochem ESR DFT; dicyclopentaannelation; hexa-peri-hexabenzocoronene; low energy gap; not-fully benzenoid PAH; open-shell biradical.
Synthesis of two dicyclopentaannelated hexa-peri-hexabenzocoronene (PHBC) regioisomers was carried out, using nonplanar oligoaryl precursors with fluorenyl groups: mPHBC I with two pentagons in the “”meta””-configuration was obtained as a stable mol., while its structural isomer with the “”para””-configuration, pPHBC II, could be generated and characterized only in situ due to its high chem. reactivity. Both PHBCs exhibit low energy gaps, as reflected by UV-vis-NIR absorption and electrochem. measurements. They also show open-shell singlet ground states according to ESR (EPR) measurements and d. functional theory (DFT) calculations The use of fully benzenoid HBC as a bridging moiety leads to significant singlet biradical characters (y0) of 0.72 and 0.96 for mPHBC I and pPHBC II, resp., due to the strong rearomatization tendency of the HBC π-system; these values are among the highest for planar carbon-centered biradical mols. The incorporation of fully unsaturated pentagons strongly perturbs the aromaticity of the parent HBC and makes the constituted benzene rings less aromatic or antiarom. These results illustrate the high impact of cyclopentaannelation on the electronic structures of fully benzenoid polycyclic aromatic hydrocarbons (PAHs) and open up a new avenue towards open-shell PAHs with prominent singlet biradical characters.
Angewandte Chemie, International Edition published new progress about Biradicals Role: FMU (Formation, Unclassified), RCT (Reactant), FORM (Formation, Nonpreparative), RACT (Reactant or Reagent). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Related Products of 576-83-0.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary