Molecular Recognition by Picolylamine- Based Tripodal Ligands and Its Application in Sensing and Asymmetric Catalysis Amanda Mickley, 1 Patrick Carney,

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Presentation transcript:

Molecular Recognition by Picolylamine- Based Tripodal Ligands and Its Application in Sensing and Asymmetric Catalysis Amanda Mickley, 1 Patrick Carney, 1 Steven Lopez, 2 Jennifer Lee, 2 and Zhaohua Dai 1,* Chemistry Departments of Pace University (1) and New York University (2)

Objective Improve the selectivity in the detection of Hg(II) through a stereochemical approach which systematically employs chiral podand, piperidine bearing ligands sulfur atoms; Improve Hg(II) sensing sensitivity by using circularly polarized fluorescence excitation (CPE); Systematically develope Fe(II) complexes of TPA-based chiral podands, piperidines and quinuclidines as green asymmetric catalysts for better product control and prediction in alkane hydroxylation by H 2 O 2. Elucidate its mechanism Elucidate mechanism to facilitate the better understanding of the interactions operating the above-mentioned molecular recognition events

Chiroptical Fluorescence Sensors for Mercury

1 st Genearation Sensor for Mercury Ratiometric Fluorescent Sensor Hg 2+

Chiroptical Response CH 3 Cu II Hg II

Pattern Recognition: Signal Selectivity -1 Hg 2+

Next Generation Sensors for Hg 2+ We intend to use these ligands to further develop circularly polarized fluorescence excitation (CPE), which is based on fluorescence-detected circular dichroism, which gives better contrast and eliminates many spectral interferences.

+ hydrolysis 1.

Alkane Hydroxylation Converting saturated C-H bonds directly into alcohols Important to synthetic organic chemistry, fuel industry and other industries using petrochemical feed stock Helpful in modeling electron-transfer processes in biological systems, and producing new catalysts

Fe(II)-TPA as Catalysts K. Chen and L. Que, Jr, JACS, 2001, 123, 6327 Ligands: Achiral; Complexes: Octahedral Products: Regio-selective, Diastereo-selective Not enantio-selective

Rigidification Enhances Enantiomeric and Regional Selectivity M. S. Chen, M. C. White. Science, 2007, 318, 783.

Our Approach Make Chiral Ligands and use their Fe-(II) complexes as catalysts Systematically rigidify the chiral ligand to improve enantio- and regio- selectivity Put Br on ligands to increase reactivity according DFT calculation Chiral podand piperidine quinuclidine

Podand and Piperidine Ligands

Synthesis of Quinuclidines

SSS-29

SSS-29 Purity and Cu(II) Complex

Acknowledgement Prof. James Canary (NYU) Prof. Demosthenese Athanasoupolos (Pace) Kirill Grinberg (Midwood High School) Funding: ACS Petroleum Research Fund Research Corporation for Science Advancement Pace University Scholarly Research Fund Pace University Kenan Faculty Development Fund