λ 3 -Phosphinino[3,2- d ]oxazoles─Condensed Phosphinines as Potential Fluorophores: Synthesis and Photophysical Study

Abstract λ3-Phosphinino[3,2-d]oxazoles are obtained from 2H-pyran-2-ones by NaOCP annulation/cyclization without intermediate purification. The 21 derivatives exhibit emission at 366–474 nm, Stokes shifts of 1747–6903 cm–1, and absolute fluorescence quantum yields of <0.1–99% in THF. Tungsten coordination gives an estimated ligand Tolman electronic parameter of 2072.3 cm–1. TD-DFT calculations on 3b and 3u illustrate contrasting excited-state structural relaxation. Phosphorus functionalization affords P(V) derivatives with altered emission wavelengths and efficiencies.

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Publication Details

Journal
Organic Letters
Published
2026-10-31
DOI
https://doi.org/10.1021/acs.orglett.6c04188
Primary Topic
Organophosphorus compounds synthesis
Type
article
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article

λ 3 -Phosphinino[3,2- d ]oxazoles─Condensed Phosphinines as Potential Fluorophores: Synthesis and Photophysical Study

Aleksandr E. Rubtsov, Ruslan I. Safiullin, Svyatoslav M. Pechenkin, Egor S. Ryabov
Organic Letters
Organophosphorus compounds synthesis
article

λ 3 -Phosphinino[3,2- d ]oxazoles─Condensed Phosphinines as Potential Fluorophores: Synthesis and Photophysical Study

Aleksandr E. Rubtsov, Ruslan I. Safiullin, Svyatoslav M. Pechenkin, Egor S. Ryabov
article en

Abstract

Abstract λ3-Phosphinino[3,2-d]oxazoles are obtained from 2H-pyran-2-ones by NaOCP annulation/cyclization without intermediate purification. The 21 derivatives exhibit emission at 366–474 nm, Stokes shifts of 1747–6903 cm–1, and absolute fluorescence quantum yields of <0.1–99% in THF. Tungsten coordination gives an estimated ligand Tolman electronic parameter of 2072.3 cm–1. TD-DFT calculations on 3b and 3u illustrate contrasting excited-state structural relaxation. Phosphorus functionalization affords P(V) derivatives with altered emission wavelengths and efficiencies.

Organic Letters
Perm State University (RU)
Openalex Percentile: Top 25%
Organophosphorus compounds synthesis
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