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Issue 44, 2016
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A solid-phase synthetic approach to pH-independent rhodamine-type fluorophores

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Abstract

An efficient methodology using the Fukuyama–Mitsunobu reaction was successfully applied to prepare various Rhodamine B-based amides with the locked possibility to form a lactam ring. The procedure was developed for solid-phase synthesis, which can be advantageously applied to the synthesis of chemical libraries in a combinatorial fashion. A series of derivatives including aliphatic as well as aromatic rhodamine amides alkylated via a reaction with various alcohols were synthesized, and their spectral properties were investigated. Blocking lactamization via N-alkylation enabled us to prepare rhodamine derivatives with an excellent fluorescence response. In comparison to their non-alkylated counterparts, these derivatives exhibited pH independence and higher quantum yields.

Graphical abstract: A solid-phase synthetic approach to pH-independent rhodamine-type fluorophores

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Publication details

The article was received on 14 Aug 2016, accepted on 10 Oct 2016 and first published on 10 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01772J
Citation: Org. Biomol. Chem., 2016,14, 10437-10443
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    A solid-phase synthetic approach to pH-independent rhodamine-type fluorophores

    L. Brulikova, Y. Okorochenkova and J. Hlavac, Org. Biomol. Chem., 2016, 14, 10437
    DOI: 10.1039/C6OB01772J

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