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Robust synthesis of NIR-emissive P-rhodamine fluorophores

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Abstract

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.

Graphical abstract: Robust synthesis of NIR-emissive P-rhodamine fluorophores

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Article information


Submitted
29 Jan 2020
Accepted
04 Feb 2020
First published
04 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Robust synthesis of NIR-emissive P-rhodamine fluorophores

M. Sauer, V. Nasufovic, H. Arndt and I. Vilotijevic, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00189A

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