Fluorescent sensing system for palladium(II) based on the Heck reaction

Yu, Suh young; Rhee, Hyun‐Woo; Hong, Jong‐In

doi:10.1016/j.tetlet.2011.01.118

Cited by 24 publications

(15 citation statements)

References 34 publications

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“…Palladium is widely used in various catalytic reactions in industry, such as in hydrogenation of unsaturated hydrocarbons, 1 as well as in automobile catalytic converters, fuel cells, jewellery and dental crowns. [2][3][4][5][6][7] Most importantly, it plays an important role in synthetic organic chemistry as a catalyst. 2,3 However, a high level of residual palladium is often found to get into the environment through the waste water system, typically due to leaching from catalysts used in synthetic protocols, resulting in a devastating impact upon the health and well-being of both humans and wildlife.…”

Section: Introductionmentioning

confidence: 99%

One-step synthesis of fluorescein modified nano-carbon for Pd(ii) detection via fluorescence quenching

Panchompoo

Aldous

Baker

et al. 2012

Analyst

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Carbon black (CB) nanoparticles modified with fluorescein, a highly fluorescent molecule, were prepared using a facile and efficient methodology. Simply stirring CB in aqueous solution containing fluorescein resulted in the strong physisorption of fluorescein onto the CB surface. The resulting Fluorescein/CB was then characterised by means of X-ray photoelectron spectroscopy (XPS), cyclic voltammetry (CV), fluorescence microscopy and fluorescence spectroscopy. The optimum experimental conditions for fluorescence of Fluorescein/CB viz. fluorescence excitation and emission wavelengths, O(2) removal and the amount of Fluorescein/CB used, were investigated. The Fluorescein/CB was used as a fluorescent probe for the sensitive detection of Pd(II) in water, based on fluorescence quenching. The results demonstrated that the fluorescence intensity of Fluorescein/CB decreased with increasing Pd(II) concentration, and the fluorescence quenching process could be described by the Stern-Volmer equation. The limit of detection (LOD) for the fluorescence quenching of Fluorescein/CB by Pd(II) in aqueous solution was found to be 1.07 μM (based on 3σ). Last, approaches were studied for the removal of Fe(III) which interferes with the fluorescence quenching of Fluorescein/CB. Complexation of Fe(III) with salicylic acid was used to enhance and control the selectivity of Fluorescein/CB sensor towards Pd(II) in the presence of Fe(III).

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Section: Introductionmentioning

confidence: 99%

One-step synthesis of fluorescein modified nano-carbon for Pd(ii) detection via fluorescence quenching

Panchompoo

Aldous

Baker

et al. 2012

Analyst

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“…In addition to non-substituted vinylbenzene, 4vinylanisole containing electron donating group and 4-(trifluoromethyl)vinylbenzene (4-TFV) containing electron withdrawing group were also tested to extend emission wavelength of the derivative induced by internal charge transfer (ICT). [17][18][19] Subsequently, we established a HPLC with fluorescence detection method for aryl bromides after pre-column derivatization with 4-VA. Oakwood products (South Carolina, USA). Palladium (II) acetate (Pd(OAc)2), N,Ndimethylacetamide (DMAc) were from Nacalai Tesque (Osaka, Japan).…”

Section: Analytical Sciencesmentioning

confidence: 99%

Long-wavelength Fluorogenic Derivatization of Aryl Halides Based on the Formation of Stilbene by Heck Reaction with Vinylbenzenes

2020

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The long-wavelength fluorogenic derivatization method for aryl halides was developed based on the stilbene formation by the Heck coupling reaction between aryl halides and vinylbenzenes in the presence of palladium (II) acetate as a catalyst.Fluorescent maximum wavelengths of the derivative obtained by the proposed reaction were 365-450 nm, which were 50-100 nm longer than those of the biphenyl derivatives formed with the our previously developed fluorogenic derivatization method. Also, by the investigation using vinylbenzenes that containing electron-donating or -withdrawing functional groups, an internal charge transfer system could contribute to extend emission wavelength of the derivative. Furthermore, the proposed reaction was applied to develop a pre-column derivatization HPLC with fluorescence detection method for aryl bromides using 4-vinylanisole. p-Substituted aryl bromides (i.e., p-bromobenzonitrile, p-bromoanisole, bromobenzene, p-bromobenzoic acid ethyl ester, p-bromotoluene) derivatives were successfully detected within 40 min with the detection limit of 0.007-0.264 µM. Despite the short reaction time of 10 min, the reaction yields for pbromoanisole and bromobenzene were good at 101% and 87%, respectively.

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“…These novel functional materials possess extremely high concentration of exposed ligands in the POLs, besides the high stability and porosity, endowing them high potential in anchoring metals. A family of novel PIPs materials with charged functional groups in the skeleton and counterions were further synthesized through the polymerization of vinyl‐functionalized ionic liquid monomers . Along with the general good nature of the POLs, a new feature of the PIPs is that the counterions can be replaced by the desired metal ions.…”

Section: Pops Polymerized By Vinyl‐based Monomersmentioning

confidence: 99%

Dual‐Ionically Bound Single‐Site Rhodium on Porous Ionic Polymer Rivals Commercial Methanol Carbonylation Catalysts

et al. 2019

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porous organic polymers (POPs) connected through strong autologous covalent bonds from vinyl-polymerization are emerging as a family of advanced materials advantageous to MOFs, because of a relatively high thermal stability of the skeleton, a hierarchical porosity, as well as the structural diversity. [4] In addition, the ligands [4] or the functional sites [5] in POPs can serve as strong anchoring sites for different metals with great tunability of the metal properties via different preparation methods, being more suitable for cataly sis. It has been believed that the chemical bond between metal species and POPs can be a coordination or an ionic bond, and the latter is generally more stable particularly under harsh reaction conditions. In this context, an effective method to create strong ionic bond is by the immobilization of the ionic active sites onto a new type of POPs with charged skeleton balanced by counterions, coined herein as porous ionic polymers (PIPs). [5] Thanks to the strong bonding and the ionic nature, the resultant single-site metal catalysts can well inherit both the advantages of homo-and heterogeneous processes, i.e., the high activity of the former and the catalyst robustness of the latter. Herein, we first briefly introduce the preparation approaches for porous organic polymers and the corresponding strategies for heterogenization of homogeneous metallic catalysts, and then exemplify a PIP hosted single-site rhodium catalyst (Rh 1 /PIP) for vapor-phase methanol carbonylation, and its excellent performance shows a promising prospect in this exciting field. POPs Polymerized by Vinyl-Based MonomersDifferent synthetic strategies have been developed to prepare POPs. [3,6] The widely used hard or soft-templates are supposed to be removed completely, requiring a highly complicated and energy-consuming procedure. [3] Moreover, the residual metals (Cu, Ni, etc.) as polymerization catalysts for Sonogashira, [7,8] Click, [9] and Yamamoto reactions [10] usually show negative impacts on the catalytic performance of POPs. Contrarily, the polymerization process of vinyl-based monomers is an exception, which can not only avoid the residue of templates and metals, but also offer excellent yields (near 100%) and simple operation. [11] Novel porous polymers can serve as self-supporting solid carriers and provide abundant coordination or charged sites for single-site metals, and thus are emerging as advanced functional materials in heterogeneous catalysis for various transformations traditionally catalyzed by homogeneous systems. A brief overview of the development of this heterogenization given, including the recent advances regarding electrovalent bonds by employing charged supports represented by porous ionic polymers (PIPs), which is exemplified herein with a novel single-site Rh 1 /PIP catalyst, featuring a new active site [Rh(CO)I 3 ] 2− dual-ionically bound onto a quaternary phosphonium cationic framework polymer, different from the single-ionically bound [Rh(CO) 2 I 2 ] − in previous studies. Such a u...

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Fluorescent sensing system for palladium(II) based on the Heck reaction

Cited by 24 publications

References 34 publications

One-step synthesis of fluorescein modified nano-carbon for Pd(ii) detection via fluorescence quenching

One-step synthesis of fluorescein modified nano-carbon for Pd(ii) detection via fluorescence quenching

Long-wavelength Fluorogenic Derivatization of Aryl Halides Based on the Formation of Stilbene by Heck Reaction with Vinylbenzenes

Dual‐Ionically Bound Single‐Site Rhodium on Porous Ionic Polymer Rivals Commercial Methanol Carbonylation Catalysts

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