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- Title
Facile Synthesis and Properties of 2-λ<sup>5</sup>-Phosphaquinolines and 2-λ<sup>5</sup>-Phosphaquinolin-2-ones.
- Authors
Vonnegut, Chris L.; Shonkwiler, Airlia M.; Khalifa, Muhammad M.; Zakharov, Lev N.; Johnson, Darren W.; Haley, Michael M.
- Abstract
Treatment of 2-ethynylanilines with P(OPh)3 gives either 2,2-diphenoxy-2-λ5-phosphaquinolines or 2-phenoxy-2-λ5-phosphaquinolin-2-ones under transition-metal-free conditions. This reaction offers access to an underexplored heterocycle, which opens up the study of the fundamental nature of the NPV double bond and its potential for delocalization within a cyclic π-electron system. This heterocycle can serve as a carbostyril mimic, with application as a bioisostere for pharmaceuticals based on the 2-quinolinone scaffold. It also holds promise as a new fluorophore, since initial screening reveals quantum yields upwards of 40 %, Stokes shifts of 50-150 nm, and emission wavelengths of 380-540 nm. The phosphaquinolin-2-ones possess one of the strongest solution-state dimerization constants for a D-A system (130 M−1) owing to the close proximity of a strong acceptor (PO) and a strong donor (phosphonamidate NH), which suggests that they might hold promise as new hydrogen-bonding hosts for optoelectronic sensing.
- Subjects
HETEROCYCLIC compounds; PHOSPHORUS compounds; COMPLEX compounds; CHEMICAL synthesis; CHEMICAL research
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 45, p13516
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201507696