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...

Full description

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00189a