Premium
Rapid Synthesis of Unsymmetrical Sulforhodamines Through Nucleophilic Amination of a Monobrominated Sulfoxanthene Dye
Author(s) -
Chevalier Arnaud,
Renault Kevin,
Boschetti Frédéric,
Renard PierreYves,
Romieu Anthony
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403165
Subject(s) - sulforhodamine b , amination , chemistry , combinatorial chemistry , amphiphile , amine gas treating , rhodamine , fluorescence , förster resonance energy transfer , dendrimer , bioconjugation , reductive amination , nucleophile , organic chemistry , copolymer , catalysis , polymer , biochemistry , physics , cytotoxicity , quantum mechanics , in vitro
A transition‐metal‐free method for the synthesis of N ‐substituted unsymmetrical sulforhodamine fluorophores from an unusual monobrominated sulfoxanthene dye and primary or secondary amines by direct S N Ar‐type reactions is presented. The simplicity and effectiveness of this “postamination” procedure were demonstrated through the rapid preparation of a library of multifunctional red‐emitting rhodamine analogues. Some of these analogues are equipped with a reactive handle and retain the two water‐solubilizing sulfonic acid moieties of the starting halogenated derivative; this makes them ideal candidates for biolabeling applications. The potential utility of this expeditious strategy to finely tune the photophysical (Stokes shift) and physicochemical properties (amphiphilic character and water solubility) of the sulforhodamine scaffold was also demonstrated through the appendage of a fluorescent amine to create a fluorescence resonance energy transfer (FRET) pair, a long‐chain amine, and tetraazamacrocycles derived from cyclen.