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Thioether Amide Based-Fluorescent Chemosensors for Pd<sup>2+</sup> with High Selectivity over Pd<sup>0</sup>
Thioether Amide Based-Fluorescent Chemosensors for Pd2+ with High Selectivity over Pd0
Bulletin of the Korean Chemical Society. 2014. Jul, 35(7): 2189-2192
Copyright © 2014, Korea Chemical Society
  • Received : March 04, 2014
  • Accepted : March 19, 2014
  • Published : July 20, 2014
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About the Authors
Sang Yeob Ahn
Sudeok Kim
Kyungkyu Baek
Min Sik Eom
Seungyoon Kang
Min Su Han

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Experimental
Chemicals . All reagents used in this work were purchased from Sigma-Aldrich Chemical Co. and were used without further purification. Pd 2+ ion solution was prepared form the respective chloride anion and DMSO, other metal ion solutions solutions were prepared from the respective perchlorate anions and deionized water.
Synthesis of N-(2-(Methylthio)ethyl)pyrene-1-carboxamide (1) . To a solution of 1-pyrenecarboxylic acid (0.25 g, 1.0 mmol) in CH 2 Cl 2 (20 mL), were added oxalyl chloride (0.38 g, 3.0 mmol) and 2 drops of DMF. After stirring for 3 h at room temperature, the solvent was removed under reduced pressure. The resulting solid was dissolved in CH 2 Cl 2 (20 mL), and then TEA (2.0 g, 20 mmol) and 1-(methylthio) ethylamine (0.14 g, 1.5 mmol) were added. After stirring for 1 h at room temperature, the solvent was removed under reduced pressure. The product was purified by silica gel chromatography with EA:Hex (1:1) as eluent. The solid product was recrystallized from MeOH to give a white solid (0.20 g, 63%): mp 161-162 °C; 1 H NMR (600 MHz, CDCl 3 ) δ 2.20 (s, 3H), 2.88 (t, 2H), 3.84 (q, 2H), 6.56 (br s, 1H), 8.03-8.23 (m, 8H), 8.61 (d, 1H); 13 C NMR (150 MHz, CDCl 3 ) δ 15.06, 34.06, 38.28, 124.34, 124.40, 124.41, 124.60, 124.78, 125.74, 125.82, 126.33, 127.11, 128.62, 128.69, 128.73, 130.70, 130.83, 131.16, 132.60, 169.98. HRMS (ESI) m/z calcd for C 20 H 18 NOS [M + H] + 320.1109; found, 320.1100.
Synthesis of N-(2-(Methylthio)ethyl)-2-(pyren-1-yl)- acetamide (2) . N -hydroxysuccinimide (0.14 g, 1.2 mol) and DCC (0.25 g, 1.2 mmol) were added to a solution of 1- pyreneacetic acid (0.26 g, 1.0 mmol) in 1,4-dioxane (20 mL). The solution was stirred for 20 h at room temperature. Ethyl acetate (30 mL) was added, and the resulting slurry was filtered. The filtrate was concentrated, the resulting solid was dissolved in 1,4-dioxane (20 mL), and 1-(methylthio) ethylamine (0.14 g, 1.5 mmol) was added. After stirring for 1 h at room temperature, the solvent was removed under reduced pressure. The product was purified by silica gel chromatography eluting with EA:CH 2 Cl 2 (1:2) to give a yellow solid (0.18 g, 55%): mp 140-141 °C; 1 H NMR (600 MHz, CDCl 3 ) δ 1.85 (s, 3H), 2.43 (t, 2H), 3.33 (q, 2H), 4.31 (s, 2H), 5.64 (br s, 1H), 7.92-8.22 (m, 9H); 13 C NMR (150 MHz, CDCl 3 ) δ 14.94, 33.58, 38.10, 42.09, 122.97, 124.63, 125.13, 125.20, 125.43, 125.54, 126.25, 127.32, 127.63, 128.25, 128.44, 128.54, 129.60, 130.80, 131.11, 131.29, 171.02. HRMS (ESI) m/z calcd for C 21 H 20 NOS [M + H] + 334.1266; found, 334.1255.
Acknowledgements
This work was supported by the Chung-Ang University Excellent Student Scholarship and Ministry of Agriculture, Food and Rural Affairs (312066-3).
References
Zhang J. F. , Zhou Y. , Yoon J. , Kim J. S. 2011 Chem. Soc. Rev. 40 3416 -    DOI : 10.1039/c1cs15028f