Robust synthesis of NIR-emissive P-rhodamine fluorophores

P-Rhodamines were accessed by implementing a robust three step sequence consisting of (i) addition of m -metallated anilines to dichlorophosphine oxides, (ii) selective dibromination, and (iii) cyclization of the diaryllithium reagents derived from the dibromides to form the dihydroacridophosphine c...

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Published in:Organic & biomolecular chemistry 2020-02, Vol.18 (8), p.1567-1571
Main Authors: Sauer, Maria, Nasufovic, Veselin, Arndt, Hans-Dieter, Vilotijevic, Ivan
Format: Article
Language:English
Subjects:
Aniline
Chemical compounds
Dibromides
Fluorescence
Fluorophores
Reagents
Rhodamine
Robustness
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container_issue 8
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creator Sauer, Maria
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Arndt, Hans-Dieter
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description P-Rhodamines were accessed by implementing a robust three step sequence consisting of (i) addition of m -metallated anilines to dichlorophosphine oxides, (ii) selective dibromination, and (iii) cyclization of the diaryllithium reagents derived from the dibromides to form the dihydroacridophosphine core of P-rhodamines. A modified route was developed to produce non-symmetric P-rhodamines. A library of prepared P-rhodamines provides first insight into dependence of fluorophore properties on the structure of P-rhodamines. A P-rhodamine with highest batochromic shifts and quantum yields in the class was identified. A library of P-rhodamines was prepared via a new robust sequence that creates the core heterocycle by addition of diaryllithium reagents to esters. The first SAR study for P-rhodamines shows that they are NIR-emissive and highly bright fluorophores.
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source Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)
subjects Aniline
Chemical compounds
Dibromides
Fluorescence
Fluorophores
Reagents
Rhodamine
Robustness
title Robust synthesis of NIR-emissive P-rhodamine fluorophores
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