Chemistry Department

About the Chemistry Department

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Chemistry Course Pages

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Recent Chemistry Department Grants

NSF Grant Summaries

Resources for Chemistry

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Fall 2009

Spring 2010

Fall 2008

Spring 2008

Fall 2007

Spring 2007

Fall 2006

Spring 2006

Fall 2005

Spring 2005

Fall 2004

Spring 2004

Fall 2003

Spring 2003

The past seven years have been busy for members of the Colby Chemistry Department. We have received over $2.4 million in research and instrumentation funding to help insure that the research experiences, instrumentation, and curriculum available at Colby are at the highest level.

2007

Jeffrey L. Katz, CAREER: Molecular design through oxacalixarenes: synthetic methods, molecular receptors, and chemical sensors, National Science Foundation, September 2007, $402,600.

With a CAREER Award from the Organic and Macromolecular Chemistry Program, Professor Jeffrey L. Katz of Colby College is developing methods for the synthesis of oxacalix[n]arenes and exploring applications of these compounds as molecular receptors and chemical sensors. A new single-step synthesis of oxacalixarenes by nucleophilic aromatic substitution of meta-diphenols with meta-dihalogenated aromatics allows access to an array of oxacalix[n]arenes bearing diverse functional groups. Naphthyridine-containing oxacalixarenes are found to act as receptors (molecular tweezers) for neutral aromatic compounds bearing hydrogen bond donors, and the optical properties of these receptors makes them potential chemical sensors for neutral organic analytes.

With the support of the CAREER award, Professor Katz will initiate a research-based mentoring program for the recruitment and retention of minority students into chemistry and other scientific disciplines. As an integral part their freshmen year and continuing throughout their undergraduate education, minority students at Colby College will have active roles in the proposed research, participate in research group meetings, attend and present posters at local and national meetings, and interact academically and socially with other student-scientists.

2005-2006

Jeffrey L. Katz, Exploiting The Oxacalixarene Scaffold:  Structural Diversity, Macrobicyclic Hosts, Multicalixarenes, and Molecular Tweezers, American Chemical Society, Petroleum Research Fund Type B Grant, September 2006, $50,000.

The Katz group is investigating the synthesis of oxygen-bridged aromatic macrocycles that can be formed by nucleophilic aromatic substitution (SNAr) reactions. While carbon-bridged [1n]metacyclophanes (calixarenes) permeate the literature of organic, supramolecular, and materials chemistry, the use of analogous oxygen-bridged structures (oxacalixarenes) lags far behind.  This is due, in large part, to the limited means of oxacalixarene synthesis.  Funded by this grant, The Katz group will explore oxacalixarene synthesis with respect to possible substitution patterns, compatible functional groups, and diversity of accessible macrocyclic ring systems.  In addition, we will investigate use of oxacalixarenes as tunable molecular tweezers for aromatic guest binding.

Julie T. Millard, Epihalohydrin Cross-Linking of DNA, American Chemical Society, Petroleum Research Fund Type B Grant, July 2006, $50,000.

Epichlorohydrin (ECH), an important industrial chemical, is a bifunctional alkylating agent with the potential to form DNA interstrand cross-links. Occupational exposure to this suspect carcinogen leads to chromosomal aberrations, and ECH has been shown to undergo reaction with DNA in vivo and in vitro. Preliminary denaturing polyacrylamide gel electrophoresis studies in our laboratory have suggested the formation of DNA cross-links by both ECH and the related compound, epibromohydrin (EBH). We propose to examine the reaction of ECH and EBH with DNA, characterizing the cross-linking in terms of sequences targeted, mechanism of reaction, and possible stereospecificity.

Jeffrey L. Katz, Heteroatom-Bridged Aromatic Macrocycles:  Development Of An Oxacalixarene-Based Molecular Toolbox, Research Corporation, Cottrell College Science Award, June 2006, $42,684.

This proposal describes a general strategy for the synthesis of oxygen-bridged aromatic macrocycles by nucleophilic aromatic substitution (SNAr) reactions. The Katz group has developed an efficient, SNAr-based construction of oxacalix[4]arenes.  Undergraduate researchers in the Katz group will explore the reaction scope of our oxacalixarene synthesis, and investigate the structural diversity of accessible macrocyclic ring systems.  Structural characterization is a key component of the described research, and X-ray crystallography will be utilized extensively for three-dimensional structural determination.

Rebecca R. Conry, Copper(I)-Arene Binding Studies with New Aryl-Appended Macrocyclic Ligands, American Chemical Society, Petroleum Research Fund Type B Grant, January 2006, $50,000.

Prof. Conry and Colby research students under her direction are preparing and studying copper(I)-arene complexes with new ligands to determine Cu(I)-arene binding strengths and locations. These basic scientific studies will primarily contribute knowledge about Cu(I)-arene interactions, for which little is known.  The results may indirectly address whether or not copper-arene binding occurs prior to copper-affected activation of an arene ring, known for both small molecule copper complexes as well as copper-containing metalloenzymes.  In addition, a determination that the Cu(I) ion binds selectively to specific arene sites may suggest similar interactions are responsible for the action of a Cu(I)-containing solid-state species known to separate isomeric alkylaromatic compounds.

2004

Julie T. Millard, Small Molecule-DNA Interactions with an Emphasis on the Mechanism of Anti-Cancer Activity, Dreyfus Foundation, Henry Dreyfus Teacher-Scholar Award, October, 2004, $60,000.

Professor Millard's reseach group is studying the DNA sequences targeted by small molecules such as diepoxybutane (DEB), the active metabolite of butadiene. DEB is an interstrand cross-linking agent, one of a number of compounds that have anti-tumor activity. Other cross-linking agents are deadly toxins. Prof. Millard's students are engaged in a number of projects to understand the role of DNA damage by these compounds in carcinogenicity and anti-tumor potential. The Henry Dreyfus Award will allow a post-doctoral Fellow to join the Millard group for the 2005-2006 academic year. This Fellow will also be involved in curricular design, particularly in a service learning course in which Colby students will develop outreach projects to take into local elementary schools.

Dasan M. Thamattoor, Catherine R. Bevier (Department of Biology), Shari U. Dunham, Jeffrey L. Katz, and Julie T. Millard, Acquisition of a Preparative HPLC System for Undergraduate Research Training in Chemistry and Biology, National Science Foundation, Major Research Instrumentation Award, July, 2004, $128,720.

This funding allowed the Chemistry and Biology Departments to purchase two preparative HPLC systems for large-scale purification of a diverse range of compounds, including precursors to carbenes, unusual aza- and oxocalixarene macrocycles, DNA-binding proteins, metal-DNA complexes, and peptides from frog skin secretions.

Jeffrey L. Katz, Synthesis of Azacalixarenes, Oxacalixarenes, and Dicalixarene Cages, Research Corporation, Cottrell College Science Award, June 2004, $39,684.

The goal of this project is the development of efficient, high yielding routs to aza- and oxocalix[n]arenes of ring sizes n = 3 to 6, as well as related muticyclic structures. Our synthetic plan will focus on one-pot, sequential SNAr reaction sequences to form each macrocycle, without having to separate mixtures of different ring sizes. Copper or palladium-catalyzed methods will be used to construct diphenylamine and diphenylether cyclization precursors. This strategy allows for both pre- and post-cyclization introduction of varied functionality on the aromatic subunits.

2003

Rebecca R. Conry: New Biomimetic Ni, Mo, and W Complexes with Derivatives of the Biphenyl-2,2'-dithiolate Ligand, Research Corporation Cottrell College Science Award, May, 2003, $39,282.

We have synthesized and fully characterized one new Mo(V)-oxo tetrathiolate complex (right) and two new Ni(II) tetrathiolate complexes (below) with the 2,2'-dimercaptobiphenyl ligand. The ligand gives unusual properties to the complexes, for example, the Ni(II) complexes are square planar in geometry (Ni(II) aryl thiolate complexes are usually tetrahedral) and both complexes bind a second metal ion on one face of the complex (in one a Na ion, in the other a Ni ion) like is known for the [NiFe]-hydrogenases, although in those enzymes it is an iron ion. However, all three complexes are oxidatively sensitive to the loss of the ligand as the disulfide. Thus, we are making new derivatives of the ligand to inhibit ligand disulfide formation so that functional models of the enzymes can be developed.

Dasan M. Thamattoor, D. Whitney King, Thomas W. Shattuck, MRI/RUI: Acquisition of a Time-Resolved Laser Flash Photolysis System for Undergraduate Research and Training in Chemistry, National Science Foundation, Award Number: 0320969, July, 2003, $108,584.

We will acquire a time-resolved laser flash photolysis system for undergraduate research and training in chemistry. This equipment will enhance research studies in a) carbene chemistry and b) the aquatic photochemistry of iron.

Julie T. Millard, AREA: Diepoxide Cross-Linking of DNA, National Cancer Institute, Grant Number: 2R15CA077748-02A1, July, 2003, $127,933.

The proposed research will examine the mediation of diepoxide cross-linking reactions by cellular proteins and will also investigate the structure-function relationship of diepoxide cross-linking reactions with the long-term goal of elucidating the mechanism of carcinogenicity versus anti-cancer chemotherapeutic potential.

Dasan M. Thamattoor, RUI: Enhancing Undergraduate Chemical Education Through Research: The Experimental and Theoretical Investigation of Unusual Carbenes, National Science Foundation, Award Number: 0315510, July, 2003, $200,000.

This proposal describes an undergraduate-oriented research program designed to study unusual carbenes generated from various cyclopropanated aromatics instead of conventional sources such as diazo compounds and diazirines.

Mark L. Wells (Univ. of Maine), Carl P. Tripp (Univ. of Maine), Karen Orcutt (Univ. of Maine), D. Whitney King (Colby), NIRT: Developing a Nanoscale Sensing Device for Measuring the Supply of Iron to Phytoplankton in Marine Systems, National Science Foundation, Award Number: 0304523, July 2003, $903,840 (the Colby portion of this grant is $285,000).

There is increasing evidence that Fe has a singularly unique role in marine ecosystems, both regulating total phytoplankton production in high nitrate, low chlorophyll regions of the world, and influencing the predominant composition of the phytoplankton assemblages found in others. The Wells group has developed liposomes that can be used to determine the biologically available Fe in sea water. These devices, 100 nm in diameter, open the way to applying nanotechnology to create a new breed of Fe biosensors in marine waters.

2002

We will acquire an isothermal titration calorimeter (ITC) and differential scanning microcalorimeters (DSC) for chemistry and biology research. Research projects that will exploit this equipment include a) structural studies of modified oligonucleotides; b) metal ion binding affinities and stabilities of modified DNA aptamers; c) binding affinities of DNA aptamers to biological targets; d) ion binding affinities and structural characterization of proteins in nematocysts; e) ion binding selectivity of polyoxa[n]peristylanes; f) computer aided molecular design and guest-host chemistry of H2-antagonists; and g) structural analysis of RNase mutants that allow self-fertilization in plants.

D. Whitney King, SGER: Exploratory Geochemistry Field Program for Minority Students , National Science Foundation, Award Number: 0220224, March, 2002, $19,969.

This small grant for exploratory research supports a geochemistry summer program for underrepresented minority students to be based at Colby College. The goal is to expose two high school juniors to the excitement of geoscience research while building their formal mathematics, chemistry, and earth science skills. The program is unique from past programs in that the students and their high school teacher are all participants in the program. Students will be selected from the High School for Engineering Professions program or the College preparatory Magnet program at Scotlandville Magnet High School in Baton Rouge, LA. The students will be part of ongoing research at Colby investigating the geochemistry of the Belgrade lakes watershed.

Julie T. Millard, In vivo mapping of diepoxybutane damage using a ligation-mediated polymerase chain reaction, Research Corporation, $33,516.

2001

The Department of Chemistry at Colby College acquired a X-ray diffractometer with CCD detector for small molecule diffractometry. This equipment will be used by five educational institutions in Maine: Colby College, Bates College, Bowdoin College, the University of Southern Maine and the University of Maine. The X-ray CCD diffractometer will enhance research in a number of areas including 1) studies of copper-arene chemistry; 2) development of new synthetic methods of selected natural products; 3) synthesis of polycyclic cage compounds with unusual architecture; 4) structure-function relationships in metalloenzymes and metalloenzymes mimics; and 5) production of C-2 symmetric lanthanocene catalyst systems and their utility in the construction of chiral molecules.

D. Whitney King, Jennifer Shosa, Robert A. Gastaldo, MRI: Integrated Sampling and Analysis Platform for the Investigation of Lake Geochemistry Over a Range of Temporal and Spatial Scales, National Science Foundation, Award Number: 0115900, August, 2001, $99,716.

We will assemble a cost-effective and technically sophisticated instrument platform for coordinated biogeochemical investigations in lakes. Fieldwork will be concentrated in the Belgrade Lakes, where both general types of Maine lakes coexist and can be compared. The integrated sampling and analysis platform will be used to investigate the spatial and temporal distribution of iron, H₂O₂, NO₃^-, and PO₄^3- in these lakes.

Dasan M. Thamattoor, Type G grant from the Petroleum Research Fund administered by the American Chemical Society, $25,000.

2000

We purchased an ion trap mass spectrometer with an electrospray interface (LC/MS) to prepare the students to be creative, independent, and well-trained scientists. The instrument is used in General, Organic, and Biochemistry courses as well as independent student research.

Stephen U. Dunham, Shari U. Dunham, Rebecca R. Conry, Thomas W. Shattuck, Dasan M. Thamattoor, Upgrade of a 400-MHz NMR Spectrometer Vital for Chemistry Research and Education, National Science Foundation, Award Number: 0079569, July 2000, $145,148.

We upgraded our 400 MHz NMR Spectrometer. This equipment will enable researchers to carry out studies on a) the isolation and identification of natural products; b) synthesis and reactivity of carbenes; c) antitumor agent development; d) nucleic acid and peptide structure/function relationships; and e) organometallic synthesis.