Electronic Materials: An Antiaromatic Propeller Made from the Four-Fold Fusion of Tetraoxa[8]circulene and Perylene Diimides.
Viktor B R PedersenStephan K PedersenZexin JinNicolaj KofodBo W LaursenGlib V BaryshnikovColin NuckollsMichael PittelkowPublished in: Angewandte Chemie (International ed. in English) (2022)
The synthesis of an antiaromatic tetraoxa[8]circulene annulated with four perylene diimides (PDI), giving a dynamic non-planar π-conjugated system, is described. The molecule contains 32 aromatic rings surrounding one formally antiaromatic planarized cyclooctatetraene (COT). The intense absorption (ϵ=3.35×10 5 M -1 cm -1 in CH 2 Cl 2 ) and emission bands are assigned to internal charge-transfer transitions in the combined PDI-circulene π-system. The spectroscopic data is supported by density functional theory calculations, and nuclear independent chemical shift calculation indicate that the antiaromatic COT has increased aromaticity in the reduced state. Electrochemical studies show that the compound can reversibly reach the tetra- and octa-anionic states by reduction of the four PDI units, and the deca-anionic state by reduction of the central COT ring. The material functions effectively in bulk hetero junction solar cells as a non-fullerene acceptor, reaching a power conversion efficiency of 6.4 %.
Keyphrases
- solar cells
- density functional theory
- molecular dynamics
- gold nanoparticles
- molecular docking
- electronic health record
- photodynamic therapy
- big data
- case control
- ionic liquid
- molecular dynamics simulations
- room temperature
- amino acid
- monte carlo
- machine learning
- high resolution
- data analysis
- artificial intelligence
- energy transfer