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Updated: Jan 9, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
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.
Abstract:
Syntheses of enantioenriched helical dispiroindeno[2,1-c]fluorenes (DSIF) possessing one or two pCp moieties are presented. These are based on the conversion of (Sp)- and (Rp) pCp-carbaldehydes 1 to triynediols 2 and 6 that were converted to enantioenriched DSIFs 4 and 8 via a catalytic [2+2+2] cyclotrimerization, oxidation, and spirocyclization sequence. Photophysical properties were measured, and compounds 4 and 8 are highly fluorescent in the violet-blue light region with |glum| values in the order of 10-4 and 10-3, and BCPL values 1.1 and 7.6, respectively.
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