A first series of fluorinated [n]helical compounds (n=5 and 6) with the dihydroindenofluorene scaffold was prepared in 5 or 9 (octafluorinated dihydroindenofluorene) steps and their photophysical properties were determined. Rh-catalyzed intramolecular [2+2+2] cyclotrimerization of triyndiols, which were prepared in a modular fashion from simple starting material such as fluorinated haloarylcarbaldehydes, to the intermediate [n]helical dihydroindeno[2,1-c]fluorene-5,8-diols was the crucial synthetic step and proceeded with high efficacy. Their further transformation gave the desired selectively fluorinated bispirodihydroindeno[2,1-c]fluorenes. Their absorption and emission spectra were recorded. The fluorescence quantum yields were up to 92 % and the emission maxima were red-shifted in comparison with their non-fluorinated counterparts (386-413 nm).

Department of Inorganic Chemistry Faculty of Science Charles University Hlavova 8 128 43 Praha 2 Czech Republic

Department of Organic Chemistry Faculty of Science Charles University Hlavova 8 128 43 Praha 2 Czech Republic

NMR Laboratory Faculty of Science Charles University Hlavova 8 128 43 Praha 2 Czech Republic

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