Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 16, Issue -, Pages 895-903Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.16.81
Keywords
donor-acceptor systems; double C-H bond activation; helicenes; pyrroles
Categories
Funding
- National Science Center of Poland [UMO-2017/27/N/ST5/00613]
- Foundation for Polish Science [TEAM POIR.04.04.00-00-5BF1/17-00]
- Ministere de l'Education Nationale, de la Recherche et de la Technologie
- Centre National de la Recherche Scientifique (CNRS)
- Rennes Metropole
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Boomerang-shaped bipyrroles containing donor-acceptor units were obtained through a tandem palladium-mediated reaction consisting of a cyclization step, involving double C-H bond activation, and a double alpha-oxygenation. The latter reaction can be partly suppressed for the least reactive systems, providing access to alpha-unsubstituted boomerangs for the first time. These alpha-free systems are highly efficient fluorophores, with emission quantum yields exceeding 80% in toluene. Preliminary measurements show that helicene-like boomerangs may be usable as circularly polarized luminescent materials.
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