4.7 Article

Amplification of the Quantum Yields of 2-λ5-Phosphaquinolin-2-ones through Phosphorus Center Modification

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 1, Pages 85-91

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02132

Keywords

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Funding

  1. National Science Foundation [INFEWS CHE-1607214]
  2. NSF [CHE-1625529]
  3. Bradshaw and Holzapfel Research Professorship in Transformational Science and Mathematics

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We report the synthesis and characterization of P-phenyl modified phosphorus- and nitrogen-containing phosphaquinolinone heterocycles. The change from -OPh to -Ph results in a marked increase in the quantum yield of the scaffold as well as a moderate red-shifting of the emission. While calculations suggest that pi to pi* transitions are dominant, intramolecular charge transfer (ICT) also contributes in the excited state. Solution- and solid-state studies of the dimerization of this new congener to the P-phenoxy variant are also reported, showing retention of the dimerization behavior in this scaffold.

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