jo5b00052_si_001.pdf (6.29 MB)
χ‑Shaped Bis(areno)-1,4-dihydropyrrolo[3,2‑b]pyrroles Generated by Oxidative Aromatic Coupling
journal contribution
posted on 2015-03-06, 00:00 authored by Maciej Krzeszewski, Daniel T. GrykoA synthesis of dihydropyrrolo[3,2-b]pyrroles fused
with two peripheral arenes or heterocyclic units has been realized
through the concise route. These nearly planar compounds were prepared
starting from assembling the central core via condensation of 2-aryl
or 2-heteroarylbenzaldehydes with aromatic amines and diacetyl, followed
by double intramolecular oxidative aromatic coupling. This two-step
procedure afforded the desired products in overall yields of 5–36%,
and it tolerates structural diversity of starting materials. All the
final dyes exhibit strong blue fluorescence in solution.