Fabrication of novel chemosensors composed of rhodamine derivative for the detection of ferric ion and mechanism studies on the interaction between sensor and ferric ion

Abstract

Although many rhodamine based fluorescence sensors were reported to detect metal ions with high sensitivity and selectivity, there are very few reports available to study the mechanisms of detection and the interaction between probe and metal ions. This paper aims to detect ferric ions by novel fluorescence chemosensors and study the mechanisms in detail. A novel probe AD-MAH-RhB was designed and synthesized from rhodamine B (RhB), adamantyl (AD), ethylene diamine and maleic anhydride (MAH). AD-MAH-RhB could detect Fe(3+) in aqueous solutions. The mechanism was explored by the HSAB principle, FTIR and mass spectra. The results suggested that Fe(3+) bound with amine and oxygen atoms in AD-MAH-RhB to form a complex composed of a 2 : 1 stoichiometry of Fe(3+) and the probe. Moreover, computational simulations were employed to further investigate the detection mechanism. The calculated results showed that Fe(3+) could conjugate with AD-MAH-RhB probe to form a stable complex, which was induced by synergetic effects of the suitable space and distance of van der Waals forces. However, Hg(2+) was found to disturb this detection and form a complex with 1 : 2 stoichiometry of Hg(2+) and AD-MAH-RhB. Then, another probe, β-cyclodextrin modified polymaleic anhydride (PMAH-CD) including AD-MAH-RhB (PMAH-CD/AD-MAH-RhB) was fabricated by inclusion interaction between CD and AD. PMAH-CD@AD-MAH-RhB showed high selectivity and sensitivity to Fe(3+) in the aqueous solution by eliminating the interruption of Hg(2+) possibly due to the high hydrogen interaction among the probes to inhibit the stable form complex with Hg(2+).

Colorimetric Metal Sensing of Fe3+ and Cr3+ and Photophysical and Electrochemical Studies Based on Benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate and Its Derivatives

“…Chelate-type Schiff base and diketopyrrolopyrrole derivatives for the detection of Fe 3+ are reported in the literature. , A fluorescent chemosensor rhodamine–aminobenzothiazole conjugate for Fe 3+ was reported by Yin et al Various rhodamine-based chemosensors for the detection of Fe 2+ and Fe 3+ have been reported. − A naphthol OH- and imine-based simple cation sensor for colorimetric detection of Fe 3+ and fluorescence turn-on response of Zn 2+ was designed by Wei et al Recently, the determination of biothiols using Fe 3+ TMB as a probe has been carried out by Liang et al A novel BODIPY-based colorimetric fluorescent chemosensor (L) with phenol as a binding site for Fe 3+ has been developed by Wang et al An imidazole-based chemosensor for the colorimetric detection of Fe 3+ and Fe 2+ was designed by Kim et al Jang et al. designed and synthesized a novel colorimetric chemosensor for sequential detection of Fe 3+ and pyrophosphate in aqueous solution .…”

Detection and Removal of Metal Ion based on a Fluorescent Sensor Composed of a Photoresponsive Rhodamine Derivative by Host-Gust Interaction

“…developed a regenerative fluorescent nanosenseor system for the selective and sensitive detection and recovery of multiple heavy metal ions based on light‐switchable monolayer self‐assembly and host–guest interactions. In our previous report, we prepared a fluorescence chemosensor based on adamantyl and maleic anhydride‐modified rhodamine B (AD‐MAH‐RhB) to detect and subsequently remove metal ions from aqueous solution simultaneously by magnetic nanoparticles composed of β‐cyclodextrin (β‐CD) . However, the probes, after forming the complex with CD, could not be recycled for further detection.…”

Structure property studies revealed a new indoylfuranone based bifunctional chemosensor for Cu2+ and Al3+

“…Once the sensing properties of a particular scaffold class (such as rhodanine, [34][35][36][37][38][39][40][41][42][43] coumarin, [44][45][46][47][48][49][50][51] Schiff base, [52][53][54][55][56][57][58][59][60] etc.) are established, its random structural modications (including simple derivatization) sometimes lead to a new molecular system with different performance indices.…”