2019
DOI: 10.1002/chem.201900136
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Intramolecular Phosphacyclization: Polyaromatic Phosphonium P‐Heterocycles with Wide‐Tuning Optical Properties

Abstract: Rationally designed cationic phospha‐polyaromatic fluorophores were prepared through intramolecular cyclization of the tertiary ortho ‐(acene)phenylene‐phosphines mediated by Cu II triflate. As a result of phosphorus quaternization, heterocyclic phosphonium salts 1 c – 3 c , derived from naphthalene, phenanthrene, and anthracene cores, exhibited very intense blue to green fluorescence ( Φ em … Show more

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Cited by 42 publications
(70 citation statements)
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“…The extension of the acene framework from naphthalene to chrysene ( 51 ) however induces blue shift of the emission ( λ em =560 nm, Φ em =0.06 in CH 2 Cl 2 ). Similarly, the binaphthyl dication 28 [56] reveals further blue shift and emits comparably to 49 ( λ em =453 nm, Φ em =0.11 in water) [57b] . On the downside, 52 possessing anthracene motif shows deep‐red fluorescence ( λ em =672 nm, Φ em =0.04 in CH 2 Cl 2 ) even without involving strong donor groups, which confirms the importance of P + ‐PAH connectivity but not only the size of the aromatic framework.…”
Section: Cyclic Organophosphorus Cationic Chromophoresmentioning
confidence: 68%
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“…The extension of the acene framework from naphthalene to chrysene ( 51 ) however induces blue shift of the emission ( λ em =560 nm, Φ em =0.06 in CH 2 Cl 2 ). Similarly, the binaphthyl dication 28 [56] reveals further blue shift and emits comparably to 49 ( λ em =453 nm, Φ em =0.11 in water) [57b] . On the downside, 52 possessing anthracene motif shows deep‐red fluorescence ( λ em =672 nm, Φ em =0.04 in CH 2 Cl 2 ) even without involving strong donor groups, which confirms the importance of P + ‐PAH connectivity but not only the size of the aromatic framework.…”
Section: Cyclic Organophosphorus Cationic Chromophoresmentioning
confidence: 68%
“…It was also noted that stoichiometric amount of PhI . Cl 2 can oxidize λ 3 σ 3 phosphine into a reactive intermediate, which quantitatively cyclizes into phosphaphenalene cation 31 (Scheme 10); [59] however this method was inefficient for the preparation of 29 ‐type salts [57b] …”
Section: Cyclic Organophosphorus Cationic Chromophoresmentioning
confidence: 99%
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“…52 A parallel also exists with the work of Romero-Nieto on the synthesis phosphonium-containing heterocycles by cyclization. 53 Hydrogen atom migration can be confirmed by the appearance of an aliphatic signal in the 1 H NMR of the compounds.…”
Section: Synthesis and Reactivity Of Cationic Phosphine Ligandsmentioning
confidence: 86%