Corannulene derivatives as non-fullerene acceptors in solution-processed bulk heterojunction solar cells

Tunable Photochemical/Redox Properties of (Phenylthio)ncorannulenes: Application to a Photovoltaic Device

“…Organothio-substituents raise HOMO and lower LUMO levels such that one can obtain good electron acceptors with smaller HOMO-LUMO gaps. 9 For example, compared to 1, a pale yellow material with first reduction at −2.33 eV in acetonitrile, decasubstitution of 1 with thiophenol (SPh) produces a deep red material with the first reduction potential at −1.22 eV, 10 which is similar to the reported value of −1.17 volts for [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM). Given that many high-performing organic photovoltaic (OPV) devices rely on C 60 and its derivatives to act as electron acceptors, 11 this similarity in electrochemistry between PCBM and decakisphenylmercaptocorannulene motivates a study into the nature of tuning the physical properties (electrochemistry, ultraviolet-visible (UV-Vis) absorption, fluorescence, and phosphorescence) of corannulene by phenylmercapto substitution and the photovoltaic characterization of decakis(phenylthio-)corannulene as an acceptor in an OPV device.…”

“…3 Curved aromatic hydrocarbons related to corannulene have been used in various materials applications including the development of fluorescent chemosensors, 4 organic field-effect transistors, 5 and heterojunction photovoltaics. 6 In each case, specific photochemical and redox properties have been important to the success of the application. Tuning the photochemical and redox properties of corannulene cognates corresponds to influencing the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels as well as the HOMO-LUMO gap.…”

“…The per-substituted phenylmercaptocorannulene is incorporated as a replacement for [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM) in a photovoltaic device. …”

Electronic transport properties of selected carbon π-bowls with different size, curvature and solid state packing

“…Corannulene, the smallest non-planar fragment of C 60 fullerene [5,6], was shown to exhibit high degree of lithium intercalation upon step-wise reduction [7][8][9][10] and corannulene-based anode materials have demonstrated a high reversible lithium capacity, almost twice as high as that of fully lithiated graphite [11,12]. The family of p-bowls also provides a natural platform for designing new organic materials with applications in light emitting-diodes [13][14][15][16], field-effect transistors [17][18][19], or photovoltaic cells [20]. While organic semiconductors may still not compete with their inorganic counterparts in terms of charge-carrier mobility or power efficiency performance, they do have the advantage of being low-cost, flexible, easily processable in solution, and compatible with many substrates [21,22].…”

Molecular Engineering of Highly Efficient Small Molecule Nonfullerene Acceptor for Organic Solar Cells

“…Several electron acceptor moieties, such as corannulene and truxenone having rotationally symmetric polycyclic aromatic cores comprising 5th and 6th membered ring have been developed for solution processable organic photovoltaic (OPV) devices. [22] A phthalocyanine based rotationally symmetric acceptor, labeled as Cl 6 -SubPc-Cl, exhibited PCE of 6.86% with SubNc donor. [23] Calamitic shaped small molecules have received immense attention recently as an effective design strategy to develop a class of high-performance NFAs.…”