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.

Department of Organic Chemistry Faculty of Science Palacký University 17 Listopadu 12 779 00 Olomouc Czech Republic

Institute of Molecular and Translational Medicine Faculty of Medicine and Dentistry Palacký University Hněvotínská 5 779 00 Olomouc Czech Republic

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