Selective recognition of fumarate from maleate with a gold nanoparticle-based colorimetric sensing system

Tetrahedron Letters

Volumn 49, Issue 22, 2008, Pages 3652-3655

  Youk, Kyung Seog ^a   Kim, Kyung Mi ^a   Chatterjee, Amrita ^a   Ahn, Kyo Han ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Colorimetric sensing; Dicarboxylates; Fumarate; Gold nanoparticles; o (Trifluoroacetyl)carboxanilides

Indexed keywords

2 (TRIFLUOROACETYL)CARBOXANILIDE DERIVATIVE; ANILIDE; DICARBOXYLIC ACID; FUMARIC ACID; GLUTARIC ACID; GOLD; MALEIC ACID; MALONIC ACID; NANOPARTICLE; OXALIC ACID; SUCCINIC ACID;

ARTICLE; BINDING SITE; COLORIMETRY; INFRARED SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 42749093181     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.142     Document Type: Article

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54. 2O (57 mg, 0.144 mmol) in deionized water (100 mL, purified by using a Milli-Q™ water purification system) under reflux was added quickly a solution of sodium citrate dihydrate (130 mg, 0.44 mmol) in deionized water (5 mL). The resulting solution became deep red within minutes, which was stirred for 30 min under reflux and then it was allowed to cool to room temperature. The reaction mixture was filtered through a cellulose nitrate membrane filter (pore size: 0.2 μm) to give a gold colloidal solution, which was diluted with deionized water (135 mL) and used for the next PVA-stabilization and TFACA-functionalization steps. To the diluted gold colloidal solution (20 mL) was added 40-80 μL of an aqueous solution of PVA (3.6 mg dissolved in 1.0 mL water; MW 9000-10,000) at room temperature. To this stabilized gold colloidal solution was added 80-μL of an acetonitrile solution of TFACA 2 (29 mg dissolved in 38 mL of acetonitrile) and the resulting mixture was stirred at room temperature for 12 h, which was used for the sensing experiments. Based on the literature data (Refs. 5c and 5d), the concentration of AuNPs in the colloidal solution is calculated to be ∼3 nM. Omitting the PVA-stabilization step in the above resulted in an unstable gold colloidal solution, which turned blue during the TFACA-functionalization.
55. As the titration proceeds, the pH of the solution became a little basic (pH 7.8 when 20 μL of 0.10 M aqueous fumarate solution was added to 2.0 mL of the AuNP solution) because of added dicarboxylate anions; however, this direct sensing scheme is preferred over that of using a buffer solution. At lower pH such as pH 6, there was no color change for the given time because some of the dicarboxylate dianions become monocarboxylate, which is unable to cross-link the nanoparticles. In the case of a more basic solution such as at pH 8 (HEPES buffer), the color change took a longer time because the binding motif becomes more hydrated as the solution becomes basic (The TFACA binding motif is under equilibrium with its hydrated form in aqueous media). When necessary, it is recommended to use a buffer solution of neutral pH or slightly basic one (pH ≤ 8).