Intramolecular Phosphacyclization: Polyaromatic Phosphonium P-Heterocycles with Wide-Tuning Optical Properties

Chemistry : a European Journal
Andrey BelyaevIgor O Koshevoy

Abstract

Rationally designed cationic phospha-polyaromatic fluorophores were prepared through intramolecular cyclization of the tertiary ortho-(acene)phenylene-phosphines mediated by CuII 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 (Φem =0.38-0.99) and high photostability in aqueous medium. The structure-emission relationship was further investigated by tailoring the electron-donating functions to the anthracene moiety to give dyes 4 c-6 c with charge-transfer character. The latter significantly decreases the emission energy to reach near-IR region. Thus, the intramolecular phosphacyclization renders an ultra-wide tuning of fluorescence from 420 nm (1 c) to 780 nm (6 c) in solution, extended to 825 nm for 6 c in the solid state with quantum efficiency of approximately 0.07. The physical behavior of these new dyes was studied spectroscopically, crystallographically, and electrochemically, whereas computational analysis was used to correlate the experimental data with molecular electronic structures. The excellent stability, water solubility, and attractive photophysical characteri...Continue Reading

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Citations

Jul 16, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Elzbieta RegulskaCarlos Romero-Nieto
Mar 12, 2020·Chemistry : a European Journal·Thomas DelouchePierre-Antoine Bouit
Jun 4, 2020·Chemistry : a European Journal·Andrey BelyaevIgor O Koshevoy
Oct 31, 2020·Chemical Communications : Chem Comm·Saskia RoeschCarlos Romero-Nieto
Sep 29, 2020·Angewandte Chemie·Philip HindenbergCarlos Romero-Nieto
Dec 19, 2019·The Journal of Organic Chemistry·Elzbieta RegulskaCarlos Romero-Nieto
Oct 14, 2021·Chemistry : a European Journal·Brenno A D NetoJohn Spencer

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Methods Mentioned

BETA
fluorescence imaging
chemical
column chromatography
X‐ray
confocal microscopy

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