Synthesis and fluorescent properties of boroisoquinolines, a new family of fluorophores

Abstract

First representatives of a new family of isoquinolines, so called boroisoquinolines, were synthesized and characterized.

Application of Boroisoquinoline Fluorophores as Chemodosimeters for Fluoride Ion and Pd (0)

“…The common intermediate for the two designed chemodosimeters was planned to be 6-fluoro-1-methyl-3, 4-dihydroisoquinoline (9) that has been synthesized by following literature procedures [20]. 3-Fluorophenyl ethaneamine was acetylated, and a modified Bishler-Napieralski reaction resulted in compound 7 with good yields.…”

“…The photospectroscopic properties might change due to a ring closure by intramolecular acylation (4), or the by the removal of the Opropargyl (5) or the O-(O-allyl) carboxyl group (6), which turns on the ESIPT (Excited State Intramolecular Proton Transfer) effect ( Figure 2). Recently, we developed a new fluorescent compound family, namely the boroisoquinolines (Figure 3, BIQ), showing good photophysical properties [20]. As the continuation of our research, we aimed to synthetize derivatives for analytical applications, in particular for the detection of fluoride (F-BIQ) and palladium (Pd-BIQ), as a development of chemodosimeters based on the novel fluorophores ( Figure 3).…”

“…We envisaged that the recognition elements would be the tertbutyldiphenylsilyl group for the fluoride anion, and the O-allyl moiety for Pd (0) sensing. Recently, we developed a new fluorescent compound family, namely the boroisoquinolines (Figure 3, BIQ), showing good photophysical properties [20]. As the continuation of our research, we aimed to synthetize derivatives for analytical applications, in particular for the detection of fluoride (F-BIQ) and palladium (Pd-BIQ), as a development of chemodosimeters based on the novel fluorophores ( Figure 3).…”

“…In most cases, the fluorophore skeleton is equipped with an O-allyl or O-propargyl group, which is removed by the palladium provoking the sensible photophysical change [17][18][19]. The photospectroscopic properties might change due to a ring closure by intramolecular acylation (4), or the by the removal of the Opropargyl (5) Recently, we developed a new fluorescent compound family, namely the boroisoquinolines (Figure 3, BIQ), showing good photophysical properties [20]. As the continuation of our research, we aimed to synthetize derivatives for analytical applications, in particular for the detection of fluoride (F-BIQ) and palladium (Pd-BIQ), as a development of chemodosimeters based on the novel fluorophores ( Figure 3).…”

Synthesis and characterization of new fluorescent boro-β-carboline dyes

“…In continuation of our research on new β-carboline derivatives 10–13 and new fluorescent agents, 14 we aimed to synthesize β-carbolines coordinating the BF 2 group either by two nitrogen atoms [like in BODIPY (9)] or a nitrogen and an oxygen [like boroisoquinolines(10) 15,16 ] ( Fig. 1 ).…”