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  • 2015 WNYACS Undergraduate Research Symposium

    The Eighth Annual

    Undergraduate Research Symposium

    Sponsored by the Western New York Section

    of the American Chemical Society

    Saturday April 11, 2015

    D'Youville College

  • 2015 WNYACS Undergraduate Research Symposium

    - 1 -

    A Message from the Organizing Committee

    Welcome to the 8th annual Undergraduate Research Symposium sponsored by the Western New York Section of the American Chemical Society! This years exciting Symposium will highlight some of the stimulating research being performed by undergraduates and their mentors from several institutions throughout Western New York and the surrounding areas, including Southern Ontario.

    I hope all participants will get the chance to engage one another in active discussions about the chemistry being presented. Please use this meeting as an opportunity to develop professionally by networking with scientific peers and faculty mentors in a relaxed scientific atmosphere. And of course, have fun!

    Thank you to all of our student presenters and especially to our keynote speaker, Prof. Huw Davies, of Emory University. I would also like to extend my appreciation to our generous sponsors and to the members of the Organizing Committee, without whom this Symposium would not be possible. Sincerely,

    Dominic L. Ventura, Ph.D. Chair, 2015 Symposium Committee

    2015 Symposium Organizing Committee

    Chair: Dr. Dominic L. Ventura Department of Math and Natural Sciences, DYouville College

    Dr. Timothy M. Gregg

    Department of Chemistry and Biochemistry, Canisius College

    Dr. Valerie A. Frerichs Department of Chemistry, University at Buffalo SUNY

    Dr. Robyn Goacher

    Department of Biochemistry, Chemistry and Physics, Niagara University

    Dr. Greg Soja Department of Math and Natural Sciences, DYouville College

  • 2015 WNYACS Undergraduate Research Symposium

    - 2 -

    Special Thanks to the Sponsors of the

    2015 Undergraduate Research Symposium

    The American Chemical Society

    D'Youville College

    Kraekler Scientific, Inc.

    Pearson Higher Education

    Shimadzu Corporation

  • 2015 WNYACS Undergraduate Research Symposium

    - 3 -

    Our Keynote Speaker

    Huw M. L. Davies

    Department of Chemistry, Emory University, Atlanta, GA

    Professor Huw M. L. Davies earned a B.Sc. in Chemistry from the University College Cardiff, Wales in 1977 and a Ph.D. in Chemistry from the University of East Anglia, England in 1980. After a postdoctoral position at Princeton University, he joined the faculty at Wake Forest University. He moved to the University at Buffalo in 1995 before joining the Department of Chemistry at Emory University in 2008, where he currently holds the position of Asa Griggs Candler Professor and is the director of Graduate Studies. Huw Davies currently holds 23 patents and is currently the director of the Center for Selective C-H Functionalization. He has also been presented several awards such as the American Chemical Society Cope Scholar award in 2005, a Fellow of the Royal Society of Chemistry in 2007, a Fellow of the American Chemical Society in 2009 and most recently he was elected a fellow of the National Academy of Inventors this past December. His research interests include investigation of dirhodium complexes as catalysts to explore novel methodolgies of donor/acceptor carbenoids to accomplish reactions such as cyclopropanation, [4+3] cycloaddition, and of course, C-H functionalization. This chemistry has also been showcased in several total syntheses to yield many natural products such as Erogorgiaene, Vibsanin E and Colombiasin A.

  • 2015 WNYACS Undergraduate Research Symposium

    - 4 -

    Schedule of Events April 11, 2015

    D'Youville College Buffalo, NY

    8:00 am-8:45 am Registration (D'Youville Academic Center, Room 216)

    8:45 am-9:00 am Introductory Remarks: Prof. Dominic Ventura

    9:00 am-10:00 am Keynote Address:

    Prof. Huw M. L. Davies, Emory University

    Collaborative Approach to C-H Functionalization

    10:00 am-11:45 am Student Oral Presentations: Moderator Prof. Greg Soja

    11:45 am-12:30 pm Lunch (College Center, Blue Lounge, 1st Floor))

    12:30 pm-2:00 pm Student Poster Presentations (College Center, Blue Lounge, 1st Floor)

    2:00 pm Symposium Awards and Closing remarks: Prof. Dominic Ventura

    Many thanks to our generous sponsors!!

  • 2015 WNYACS Undergraduate Research Symposium

    - 5 -

    Oral Presentations 9:00 AM - 11:45 AM (DAC 216)

    Keynote Address

    9:00 AM Huw M. L. Davies, Ph.D. Emory University

    Collaborative Approach to C-H Functionalization

    Student Presentations

    1. 10:00 am Cassidy Benson SUNY Fredonia Characterizing Novel Solid-State Reaction Intermediates Using Advanced In

    Situ X-Ray Diffraction Techniques

    2. 10:15 am Jessica H. Ciesla SUNY College of Environmental Science and Forestry Progress Towards the Synthesis and in vivo Incorporation of Click-Ready Fatty

    Acids into Poly-[(R)-3-hydroxyalkanoate] Biopolymers

    3. 10:30 am J. O. Ellison The College at Brockport, SUNY Computational Study of Imidazolium Ionic Liquid Solvation

    4. 10:45 am Samantha Livingston Niagara University Determining Order of Black Ballpoint Pen Ink Deposition on Paper to Identify Forgeries in

    Questioned Documents Using Time-of-Flight Secondary Ion Mass Spectrometry

    5. 11:00 am Kevin Sidoran St. Bonaventure University Gold(I) Complexes Featuring Ferrocenylated N-Heterocyclic Carbenes for

    Anticancer Studies

    6. 11:15 am Daniel Snyder DYouville College Synthesis of Novel Glassy Liquid Crystalline Compounds from Cholesterol

    Derivatives

    7. 11:30 am Sara J. Stonehouse McMaster University Syntheses and Characterization of Fluoroborate Salts of Noble-Gas

    Fluorocations and the [O2]+ Cation

  • 2015 WNYACS Undergraduate Research Symposium

    - 6 -

    Abstracts

    Collaborative Approach to C-H Functionalization

    Huw M. L. Davies

    Department of Chemistry, Emory University, Atlanta, GA

    Traditionally, the synthesis of complex organic compounds has relied on a carefully orchestrated strategy of reactions involving modification of functional groups. This presentation will describe an alternative approach, in which the transformations will occur at C-H bonds rather than the functional groups. This changes the logic of organic synthesis and offers exciting new approaches for the synthesis of fine chemicals for materials science and drug development.

    REACTIVE SITES FOR CH FUNCTIONALIZATION

    NO

    O

    Br

    REACTIVE SITES FOR FUNCTIONAL GROUP MODIFICATION

  • 2015 WNYACS Undergraduate Research Symposium

    - 7 -

    Talk 1

    Characterizing Novel Solid-State Reaction Intermediates Using Advanced In Situ X-Ray

    Diffraction Techniques

    Cassidy Benson1, Jordan Cox2, Ian Walton2 and Jason B. Benedict2*

    1Department of Chemistry, SUNY Fredonia, Fredonia NY 2Department of Chemistry, University at Buffalo, SUNY, Buffalo NY

    In permanently porous metal-organic frameworks (MOFs) there exist continuous channels that allow for the dynamic exchange of guest molecules. X-ray diffraction (XRD) remains one of the most powerful techniques for determining the structure of crystalline MOFs at atomic resolution. This work highlights recent progress in the design and construction of a novel apparatus for monitoring the process of guest exchange in situ by XRD, with the ultimate goal of developing a molecular-level understanding of the fundamental processes occurring within these materials.

  • 2015 WNYACS Undergraduate Research Symposium

    - 8 -

    Talk 2

    Progress Towards the Synthesis and in vivo Incorporation of Click-Ready Fatty Acids into

    Poly-[(R)-3-hydroxyalkanoate] Biopolymers

    Jessica H. Ciesla, Atahualpa Pinto and Christopher T. Nomura*

    Department of Chemistry, SUNY College of Environmental Science and Forestry, Syracuse, NY Poly-[(R)-3-hydroxyalkanoate] biopolymers, or PHAs, are biocompatible and biodegradable polyesters produced natively by diverse microbial strains. PHA polymers have widespread uses in applications ranging from sustainable replacements of non-biodegradable bulk-commodity plastics to biomedical materials. Development of nanoparticle drug delivery therapeutics with PHA polymers have been tested and found effective in targeted delivery of cytotoxic drugs to cancer cells. Research is limited by a lack of control over the repeating unit composition and inability to chemically modify these polymers with ease. To tackle these problems, efforts have centered in metabolically engineering heterologous microbe strains to yield rationally designed PHAs. Recently, our lab engineered E. coli LSBJ, a microbial strain able to produce PHA copolymers with controlled unit compositions from simple and accessible fatty acid feedstocks. Expanding on this technology, we have been enthusiastically exploring our strains flexibility to uptake and incorporate unusual/synthetic fatty acids into PHA copolymers. We envision meaningfully broadening the application spectrum of these materials via production of chemically tractable PHA biopolymers containing click-ready chemical functionalities. With biomedical applications in mind, in this study we demonstrate the in vivo polymerization of click-ready synthetic 10-azidodecanoic acid and take the first exploratory steps towards the synthesis and incorporation of 6-azidohexanoic acid into PHA polymers. Our

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