Probe and dye design through copper-mediated reactions of N-arylhydroxylamines

Abstract

A phthalimide probe (P1) possessing a hydroxylamine group on the benzene ring has been prepared for fluorescence sensing of copper ions. The detection is based on the reaction between hydroxylamine...

A Green-Emitting Luminol Analogue as the Next-Generation Chemiluminescent Substrate in Biochemical Analysis

“…3-Hydroxyphthalimide and 4-aminophthalimide derivatives are excited-state intramolecular proton transfer (ESIPT) fluorophores. Moreover, these phthalimides are a type of ultrasmall dyes with typical bright green emission, whose fluorescence quantum yields are usually larger than 0.3 in aqueous medium . To prepare a new phthalhydrazide derivative that potentially has green CL, 3-hydroxyphthalimide was introduced to luminol to form GL-1 .…”

“…Moreover, these phthalimides are a type of ultrasmall dyes with typical bright green emission, whose fluorescence quantum yields are usually larger than 0.3 in aqueous medium. 24 To prepare a new phthalhydrazide derivative that potentially has green CL, 3-hydroxyphthalimide was introduced to luminol to form GL-1. Only a single-step reaction was required, and a high isolated yield (80%) was achieved (Scheme 1 and Scheme S1).…”

A mitochondrion-targeted fluorescent probe based on ESIPT phthalimide for the detection of Hg2+ with large Stokes shift

“…19 ESIPT fluorophores have large Stokes shifts, which can avoid self-absorption and inner-filter effects; hence ESIPT-based fluorescent probes have been extensively studied. 20–27 Phthalimide derivatives are the typical representative of ESIPT fluorescent dyes with the merits of simple synthesis, good photostability, high quantum yield, large Stokes shift, and biocompatibility. 21–27 Currently, phthalimide-based fluorescent probes have been utilized to detect carbon monoxide (CO), 21 S -nitrosoglutathione (GSNO), 22 hydrogen peroxide (H 2 O 2 ), 23 palladium, 24 copper ions, 25 fluoride ion (F − ), 26 and peroxynitrite (ONOO − ).…”

“…20–27 Phthalimide derivatives are the typical representative of ESIPT fluorescent dyes with the merits of simple synthesis, good photostability, high quantum yield, large Stokes shift, and biocompatibility. 21–27 Currently, phthalimide-based fluorescent probes have been utilized to detect carbon monoxide (CO), 21 S -nitrosoglutathione (GSNO), 22 hydrogen peroxide (H 2 O 2 ), 23 palladium, 24 copper ions, 25 fluoride ion (F − ), 26 and peroxynitrite (ONOO − ). 27 However, as far as we know, phthalimide-based Hg 2+ -specific fluorescent probes have not yet been reported.…”