5,14-Diaryldiindeno[2,1- f:1',2' -j]picene: A New Stable [7]Helicene with a Partial Biradical Character.
Ya-Chu HsiehCheng-Feng WuYi-Ting ChenChia-Te FangChi-Shin WangChia-Hsin LiLiang-Yu ChenMu-Jeng ChengChu-Chen ChuehPi-Tai ChouYao-Ting WuPublished in: Journal of the American Chemical Society (2018)
5,14-Diaryldiindeno[2,1- f:1',2' -j]picene (DDP, 1), a thermally and chemically stable helical arene, can be prepared from 1,4-bis[2-(arylethynyl)phenyl]benzene in four synthetic steps. Its helical backbone, which incorporates an o-quinodimethane moiety, was verified by X-ray crystallography, and this structural feature results in a very high barrier to racemization (exceeding 50 kcal/mol). DDP possesses versatile and promising properties, including a small HOMO-LUMO energy gap (1.31 eV for the dimesityl-substituted derivative 1ab), an electron spin resonance (ESR)-active character, a small triplet-singlet energy gap (4.75 kcal/mol), broad photoabsorption covering the ultraviolet, visible, and near-infrared (NIR) regions, two-photon absorption in the NIR range, and respectable ambipolar charge-transport behavior in a solution-processed organic field-effect transistor.
Keyphrases
- energy transfer
- water soluble
- photodynamic therapy
- fluorescent probe
- drug release
- fluorescence imaging
- living cells
- high resolution
- machine learning
- solar cells
- electron microscopy
- deep learning
- density functional theory
- room temperature
- light emitting
- single molecule
- quantum dots
- estrogen receptor
- magnetic resonance imaging
- transition metal
- contrast enhanced