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Helical Dispiroindeno[2,1-c]fluorenes Possessing Planar Chirality: Synthesis and Chiroptical Properties
Marko Bogomolec1, Lucia Feriancová1, Jhon Sebastian Oviedo Ortiz2
1Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, Praha 2, Prague 128 00, Czech Republic.
Researchers synthesized enantioenriched helical dispiroindeno[2,1-c]fluorenes (DSIF) with pCp moieties. These novel compounds exhibit strong violet-blue fluorescence and potential for chiroptical applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Helical organic molecules offer unique chiroptical properties.
- Dispiroindeno[2,1-c]fluorenes (DSIF) are a class of complex polycyclic aromatic hydrocarbons.
- Incorporating chiral elements into DSIF structures is key for advanced applications.
Purpose of the Study:
- To synthesize novel enantioenriched helical dispiroindeno[2,1-c]fluorenes (DSIF) with pCp moieties.
- To investigate the photophysical properties of these chiral DSIF compounds.
- To explore their potential in chiroptical applications.
Main Methods:
- Synthesis of pCp-carbaldehydes and conversion to triynediols.
- Catalytic [2+2+2] cyclotrimerization for DSIF core formation.
- Oxidation and spirocyclization to yield enantioenriched DSIFs.
Main Results:
- Successful synthesis of enantioenriched DSIFs (compounds 4 and 8) with pCp groups.
- Compounds exhibit strong fluorescence in the violet-blue region.
- High luminescence dissymmetry factor (|g_lum|) and circular brightness (B_CPL) values were observed.
Conclusions:
- Enantioenriched DSIFs with pCp moieties can be efficiently synthesized.
- These DSIFs possess significant photophysical properties, including strong fluorescence and chiroptical activity.
- The synthesized DSIFs show promise for applications in chiral optoelectronics and sensing.
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