Synthesis of Bioctacene-Incorporated Nanographene with Near-Infrared Chiroptical Properties.
Xiushang XuRafael Muñoz-MármolSerhii VasylevskyiAndrea VillaGiulia FolpiniFrancesco ScotognellaGiuseppe Maria PaternòAkimitsu NaritaPublished in: Angewandte Chemie (International ed. in English) (2023)
We report the synthesis of a hexabenzoperihexacene (HBPH) with two incorporated octacene substructures, which was unambiguously characterized by single-crystal X-ray analysis. The theoretical isomerization barrier of the (P,P)-/(P,M)-forms was estimated to be 38.4 kcal mol -1 , and resolution was achieved by chiral HPLC. Notably, the enantiomers exhibited opposite circular dichroism responses up to the near-infrared (NIR) region (830 nm) with a high g abs value of 0.017 at 616 nm. Moreover, HBPH demonstrated NIR emission with a maximum at 798 nm and an absolute PLQY of 41 %. The excited-state photophysical properties of HBPH were investigated by ultrafast transient absorption spectroscopy, revealing an intriguing feature that was attributed to the rotational and/or conformational dynamics of HBPH after excitation. These results provide new insight into the design of chiral nanographene with NIR optical properties for potential chiroptical applications.
Keyphrases
- photodynamic therapy
- single molecule
- fluorescence imaging
- capillary electrophoresis
- high resolution
- solid state
- drug release
- ms ms
- mass spectrometry
- fluorescent probe
- atomic force microscopy
- machine learning
- ionic liquid
- energy transfer
- deep learning
- simultaneous determination
- molecular dynamics
- molecular dynamics simulations
- magnetic resonance imaging
- high performance liquid chromatography
- drug delivery
- cerebral ischemia
- dual energy
- risk assessment
- solid phase extraction
- brain injury
- blood brain barrier
- electron microscopy