Luminescent 1<i>H</i>-1,3-benzazaphospholes

Evariste, Sloane; Harrison, Alexandra M.; Sarkar, Sunandan; Rheingold, Arnold L.; Dunietz, Barry D.; Heinicke, Joachim; Emalyn, Delgado Rosario,; Yoon, Subin; Teets, Thomas S.; Protasiewicz, John D.

doi:10.1039/d2ra07226b

RSC Adv.

2023

DOI: 10.1039/d2ra07226b

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Luminescent 1H-1,3-benzazaphospholes

Sloane Evariste

Alexandra M. Harrison

Sunandan Sarkar

et al.

Abstract: 2-R-1H-1,3-Benzazaphospholes (R-BAPs) are an interesting class of fluorescent σ2P heterocycles containing PC bonds.

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Cited by 3 publications

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Probing Radical Addition to 1‐Phosphabutadienes by Employing Muonium as a “Light Isotope” of Hydrogen

Walsgrove,

Percival,

Gates

2023

Chemistry A European J

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Understanding free radical addition to multiple bonds is important to elucidating the mechanistic details of addition polymerization reactions, albeit the fleeting radical intermediates are very difficult to detect by conventional methodologies. Muon spin spectroscopy (μSR) is a highly sensitive method that can detect radical species at 106 spins (cf. EPR: 1012 spins, NMR: 1018 spins). Herein, we employ μSR to detect the radical‐addition products from three 1‐phosphabutadiene monomers, P‐analogues of isoprene. We show that muonium (Mu), a “light” H‐atom surrogate, adds predominantly at the C4 position of the P1=C2−C3=C4 moiety to give unprecedented 1‐phosphaallyl radicals as the major products. Our structural assignments are supported by assignment of muon, phosphorus and proton hyperfine coupling constants using DFT‐calculations. A minor radical product is also detected that is tentatively assigned to an PC3‐heterocyclic free radical. On the basis of DFT‐predictions, we speculate that its formation may involve initial addition of Mu+ at the C3 position followed by electron capture. These studies provide rare insights into the prospective radical (or cationic) polymerization of 1‐phosphabutadienes, which have previously been polymerized using anionic initiation.

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Probing Radical Addition to 1‐Phosphabutadienes by Employing Muonium as a “Light Isotope” of Hydrogen

Walsgrove,

Percival,

Gates

2023

Chemistry A European J

View full text Add to dashboard Cite

show abstract

Convenient access to π-conjugated 1,3-azaphospholes from alkynes via [3 + 2]-cycloaddition and reductive aromatization

Fidelius,

Schwedtmann,

Schellhammer

et al. 2024

Chem

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Influence of the substituents on physico-chemical properties of 1-R-1,2-diphospholes: Theoretical and experimental study

Zagidullin,

Sakhapov,

Saitova

et al. 2024

Journal of Organometallic Chemistry

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Luminescent 1H-1,3-benzazaphospholes

Abstract: 2-R-1H-1,3-Benzazaphospholes (R-BAPs) are an interesting class of fluorescent σ2P heterocycles containing PC bonds.

Cited by 3 publications

References 98 publications

Probing Radical Addition to 1‐Phosphabutadienes by Employing Muonium as a “Light Isotope” of Hydrogen

Probing Radical Addition to 1‐Phosphabutadienes by Employing Muonium as a “Light Isotope” of Hydrogen

Convenient access to π-conjugated 1,3-azaphospholes from alkynes via [3 + 2]-cycloaddition and reductive aromatization

Influence of the substituents on physico-chemical properties of 1-R-1,2-diphospholes: Theoretical and experimental study

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