New Synthesis of a Dibenzoperylene Motif Featuring a Doubly Boron–Nitrogen-Doped Bay Region

Abstract

A dibenzoperylene motif featuring a doubly boron–nitrogen-doped bay region is accessible from an aniline derivative in six steps in good overall yield. Two n-butyl groups provide the BN-doped polycyclic aromatic hydrocarbon with sufficient solubility in common organic solvents. The synthesis sequence allows installation of a second boron atom next to a weakly nucleophilic nitrogen by using a protected boron species. The title compound shows blue fluorescence, an extremely high fluorescence quantum yield, and an interesting doped bay region.

Recent Advances in the Luminescence of Arylboronic Acids and their Heteroatom Condensates

“… Borazine fragments and all‐carbon comparators reported by Bettinger et al [30] . a) The borazines 13 and 14 exhibit a perylene motif (outlined in blue).…”

“…The Bettinger laboratory would later apply this trimer as a synthetic precursor to create two borazines bearing a perylene motif [30] . Following photochemically‐induced oxidative C−C bond formation, one compound, 13 , could have its central B 3 N 3 core hydrolyzed to give a BNBN fragment 14 (Figure 10a).…”

Heteroatom Cycloaddition at the (BN)2Bay Region of Dibenzoperylene

“…Perylenes and dibenzoperylenes with BN doping have been synthesized by Wagner, Bonifazi and our group [3b, 4j, 8, 10] . We have developed a multistep synthesis of a dibenzoperylene 1 that features a BNBN unit at its bay region [4j] .…”

Heteroatom Cycloaddition at the (BN)2Bay Region of Dibenzoperylene

“…Perylenes and dibenzoperylenes with BN doping have been synthesized by Wagner, Bonifazi and our group [3b, 4j, 8, 10] . We have developed a multistep synthesis of a dibenzoperylene 1 that features a BNBN unit at its bay region [4j] . It would be interesting to use this heterodiene as functional group for widening the chemical space in heteroatom doped PAH synthesis by cycloaddition reactions.…”