1245928-51-1Relevant articles and documents
O-Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes
Dor?evi?, Luka,Allain, Magali,Bonifazi, Davide,Coronado, Eugenio,Demitri, Nicola,Folli, Andrea,Mézière, Cécile,Ma?as-Valero, Samuel,Murphy, Damien,Sallé, Marc,Valentini, Cataldo
, p. 4106 - 4114 (2020)
Herein we report an efficient synthesis to prepare O-doped nanographenes derived from the π-extension of pyrene. The derivatives are highly fluorescent and feature low oxidation potentials. Using electrooxidation, crystals of cationic mixed-valence (MV) complexes were grown in which the organic salts organize into face-to-face π-stacks, a favorable solid-state arrangement for organic electronics. Variable-temperature electron paramagnetic resonance (EPR) measurements and relaxation studies suggest a strong electron delocalization along the longitudinal axis of the columnar π-stacking architectures. Electric measurements of single crystals of the MV salts show a semiconducting behavior with a remarkably high conductivity at room temperature. These findings support the notion that π-extension of heteroatom-doped polycyclic aromatic hydrocarbons is an attractive approach to fabricate nanographenes with a broad spectrum of semiconducting properties and high charge mobilities.
O-Annulation to Polycyclic Aromatic Hydrocarbons: A Tale of Optoelectronic Properties from Five- To Seven-Membered Rings
Dordevi?, Luka,Milano, Domenico,Demitri, Nicola,Bonifazi, Davide
supporting information, p. 4283 - 4288 (2020/06/24)
We take advantage of the Pummerer oxidative annulation reaction to extend PAHs through the formation of an intramolecular C-O bond with a suitable phenol substituent. Depending on the peripheral topology of the PAH precursor (e.g., pyrene, boron-dipyrromethene, or perylene diimide) five-, six-, and seven-membered O-containing rings could be obtained. The effect of the O-annulations on the optoelectronic properties were studied by various methods with the pyrano-annulated pyrene and BODIPY derivatives depicting quantitative emission quantum yields.