title: A solid-phase synthetic approach to pH-independent rhodamine-type fluorophores.
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.
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University, 17. Listopadu 12, 779 00 Olomouc, Czech Republic. jan.hlavac@upol.cz.
authors.forename: L
authors.initials: L
authors.lastname: Brulikova
authors.affiliation: Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech Republic.
authors.forename: Y
authors.initials: Y
authors.lastname: Okorochenkova
authors.affiliation: Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech Republic.
authors.forename: J
authors.initials: J
authors.lastname: Hlavac