ИСТИНА

Bowl-shaped polycyclic aromatic hydrocarbons (PAH) or buckybowls are pyramidalized polyenes composed of fused hexagons and pentagons which can be considered as substructures of fullerenes. Buckybowls demonstrates superior acceptor properties as compared to planar PAH [1]. Their moderate solubility and stability during sublimation comparable with planar PAH are of key relevance for fabrication of thin film organoelectronic devices. Recently reported efficient strategy for the direct synthesis of functional buckybowls via fluorine promoted Aryl-Aryl coupling with quantitative yields [2] significantly broaden scope of synthetically available buckybowls with desired carbon frameworks. Here we report the features of molecular and electronic structures of indaceno[3,2,1,8,7,6-pqrstuv]picene (I) and diindeno[4,3,2,1-cdef:4’,3’,2’,1’-lmno]chrysene (II) frameworks prepared via fluorine promoted Aryl-Aryl coupling. The derivatives were spectroscopic characterized, their electrochemical behavior, reduction and oxidation potentials were measured by means of cyclic voltammetry. The estimated ELUMO energy levels of the compounds and electrochemical reversible behavior evidence the potential applicability of these derivatives as acceptor material for polymer solar cells (PSCs). Fabricated buckybowl-based PSC devices demonstrated higher the open-circuit voltage values in comparison with the reference PC60BM-based devices. This work was supported by RFBR (project № 17-03-00488 А). [1] C. Koper, M. Sarobe, L.W. Jenneskens, Redox properties of non-alternant cyclopenta-fused polycyclic aromatic hydrocarbons: The effect of peripheral pentagon annelation, Phys. Chem. Chem. Phys. 6 (2004) 319–327. doi:10.1039/B312234D. [2] K.Y. Amsharov, M.A. Kabdulov, M. Jansen, Facile Bucky-Bowl Synthesis by Regiospecific Cove-Region Closure by HF Elimination, Angew. Chem. Int. Ed. 51 (2012) 4594–4597. doi:10.1002/anie.201200516.