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The Hilmey Research Group: (From left) Xavier Hilmey, Umar Asif ('14), Tina Boortalary ('15),
Kelly Morrison ('13), Dr. David Hilmey, Aashish Abraham ('13), Rory Jones ('14), Aditya Rao ('14),
Lori Kim ('16). Junebug Hilmey is in front.
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Overview of Research
1. Dihalogenated polyaromatics as precursors for graphene nanoribbon synthesis
The growth of nanotechnology and the need for nanosized materials has pushed material science towards the molecular scale. Bottom-up fabrication of graphene nanoribbons (GNRs) exemplifies the utility of synthetic organic chemistry in the fabrication of nanomaterials. Our research is focused on the generation precursors for the fabrication of GNRs with tunable widths and edge states. This collaboration, with Dr. Sarbajit Banerjee at the University at Buffalo, involves the synthesis of a library of dihalogenated polyaromatic molecules. Students gain synthetic and problem solving skills and will be exposed to analytical, physical, and computational chemistry through collaboration with Dr. Banerjee. At UB, the
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synthesized small molecules will be subjected to graphene nanoribbon fabrication through solvothermal annealing.
Current students: Umar Asif, Kelly Morrison.
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2. Novel ring chemistry of Vitamin B6
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Vitamin B6, pyridoxine, reacts with singlet oxygen, 1O2, in aqueous solution at neutral pH resulted in oxidation at the 2- and 6-positions of the pyridine ring and unprecedented ring contraction. Kinetic and low temperature studies provide observable intermediates by NMR spectroscopy. In addition to the 1O2 reaction, novel cycloaddition between pyridoxine and N-methylmaleimide suggest a [3+2] cycloaddition with the 3-hydroxypyridine ring. This research opens the door to new biochemical possibilities for Vitamin B6 and its various forms.
Current students: Aditya Rao, Lori Kim.
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3. Lithium specific cages
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Acyclic organic scaffolds with a 1,3-pattern of polyoxygenation similar to natural polyketides are being explored. In-depth conformational analysis, in concert with experimental results, will enhance our understanding of molecules whose unshared electron pairs, polar bonds, and hydrogen bonding determine overall molecular orientation. Less than ten steps would be required for each scaffold’s construction with only several carbon-carbon bond forming reactions. Analysis of the polyketide-like systems will focus on conformational analysis through computational chemistry as well as NMR analysis. Ideally, these compounds will exhibit desirable characteristics such as helical self-association, enhanced binding, or specific metal-binding properties.
Current students: Aashish Abraham, Tina Boortalary.
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4. Synthesis of enzyme inhibitors to study the degradation of niacin by bacteria
The oxidative degradation of niacin (vitamin B3) to fumarate in several species of aerobic bacteria includes the hydrolytic deamination of maleamate to maleate, catalyzed by maleamate amidohydrolase (NicF). NicF from Bordetella bronchiseptica is currently under investigation by Dr. Mark Snider (Wooster) and Dr. Roger Rowlett (Colgate). A hydrolysis mechanism associated with NicF is proposed and development of small molecule inhibitors which are structurally similar to maleamate should help define the active site organization and mechanism of action of NicF.
Current student: Rory Jones.
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Aashish describes the perfect throwing motion for a bocce game during the annual Hilmey group picnic in May of 2013.
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Highlights from Conferences
Western New York American Chemical Society Undergraduate Research Symposium at Niagara University, Spring 2013.
Kelly Morrison ('13) and Umar Asif ('14) describe their syntheses of
graphene nanoribbon precursors to Dr. Sarbajit Banerjee, an expert
in the field of graphene and nanocrystals.
The Hilmey Research Group travels to Niagara University to support their presenting labmates:
Aditya Rao ('14), Kelly Morrison ('13), and Umar Asif ('14).
Rochester Academy of Science Fall 2011 Scientific Papers Day: David Samuel ('12) presented his research, performed in Dr. Hilmey's lab, to a group of faculty and students from Western and Central New York at the RAS Fall 2011 Scientific Papers Day on Oct. 29. Samuel's talk, “NMR Characterization and Mechanistic Implications of Singlet Oxygen Addition to the Vitamin B6 Ring”, focused on new products and intermediates of oxidation of vitamin B6.
David Samuel ('12) presents his research at the RAS Fall 2011 Conference.
Rochester Academy of Science Fall 2010 Scientific Papers Day: While at St. Bonaventure, Kirsten Norrell ('10) conducted research with Dr. David Hilmey on the oxidation of vitamin B6. On November 6, 2010, Kristen presented her research at the RAS Scientific Papers Day at RIT.
Kristen describes her research on the oxidation of vitamin B6 to conference attendees.