Dibenzo[ a,o ]picene: A Semiconducting Nonplanar Heptacene Isomer
Abstract
We report a concise two-step synthesis of the elusive heptacene isomer dibenzo[ a,o ]picene via regioselective Mallory photocyclization of a bis(stilbenyl)phenanthrene precursor. DFT calculations rationalize the observed regioselectivity and confirm the aromatic, highly stable framework. Dibenzo[ a,o ]picene exhibits a 2.98 eV optical band gap, reversible oxidation, and a low-lying HOMO. Single-crystal X-ray analysis reveals one-dimensional π-stacking (3.31 Å). Single-crystal OFETs display p-type hole mobilities of 3.2 × 10 –3 cm 2 V –1 s –1, establishing this long-sought isomer as a promising air-stable semiconductor.
Fields of Study & Subjects
Synthesis and Properties of Aromatic Compounds
Organic Electronics and Photovoltaics
Luminescence and Fluorescent Materials
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 3
- Pages
- 977–981
- Publication date
- 8 January 2026
- Language
- EN