David V Dearden, Roger G Harrison, John D Lamb, Chemistry and Biochemistry

Evaluation of how well the academic objectives of the proposal were met

The goal of this proposal was to train graduate and undergraduate students through research experiences in supramolecular chemistry in a multi-group environment. Academically, our objective was to synthesize and characterize new supramolecular host molecules and to develop applications for these molecules. We believe we have been quite successful, as demonstrated by the presentations and publications listed below and as shown by the receipt of a National Science Foundation grant by one of the teams involved in this research, in a year when such grants were particularly difficult to obtain.

Evaluation of the mentoring environment

The mixed undergraduate/graduate student environment of our program has worked very well. Typically, new undergraduate or graduate students initially worked with a more experienced student until they developed the skills and confidence needed to work on their own. Graduate students provided the longer-term continuity essential to success, while undergraduate students added essential manpower and enthusiasm and helped keep the personnel at “critical mass.” The whole effort was overseen by three faculty members who coordinated the work, gave direction to the research, and sought outside funding. Weekly group meetings and monthly joint meetings of all three groups gave the students opportunities to present and discuss their work in a friendly environment and to receive guidance from all the group members.

List of students who participated and what academic deliverables they have produced

Student	Undergraduate (UG) or Graduate (G)
Courtney Britsch	UG
Jordan Cardinal	UG
Karla Castro	UG
Conner Harper	UG
Sam Hickenlooper	UG
Chad Jones	G
Spencer Krieger	UG
Holly Larson	UG
Na Li	G
Tayyebeh Panahi	G
Joshua Pothoof	UG
Spencer Rushton	UG
Max Scoville	UG
Jiewen Shen	G
Spencer Wallentine	UG
Doug Weaver	UG
Anupriya	G

Presentations

• Tayyebeh Panahi “Synthesis of Deep Chiral Resorcinarene Cavitands and their Application in Chiral Recognition, Separation and Ion Chromatography” Student Research Conference, BYU, Provo, Utah, March 9, 2013.
• Joshua Pothoof “Synthesis and Properties of Encapsulation Molecular Bowl with Zn Arm” Student Research Conference, BYU, Provo, Utah, March 9, 2013.
• Tayyebeh Panahi “Deep Cavity Cavitands with Amino Acid Groups” Utah Academy of Sciences, UVU, Orem, Utah April 12, 2013. Tayyebeh Panahi, Josh Pothoof, Holly Larson “Cavitands with amino acid groups for IC separations” National Chemistry Week Poster Session, BYU, Provo, Utah, October 25, 2013.
• Tayyebeh Panahi “Separation of Guanadine compounds by resorcinarene-based solid phases” PittConn, Chicago, Illinois, March 4, 2014.
• Holly Larson “Synthesis of Resorcinarene Molecules Containing Glutamic Acid” Student Research Conference, BYU, Provo, Utah, March 15, 2014.
• Tayyebeh Panahi “Direct Determination of Guanidine Compounds in Water with a Cavitand-Based Stationary Phase” Student Research Conference, BYU, Provo, Utah, March 15, 2014.
• Tayyebeh Panahi, Holly Larson, Spencer Wallentine, Karla Castro “Cavitands with amino acid groups for IC separations” National Chemistry Week Poster Session, BYU, Provo, Utah, October 24, 2014.
• Doug Weaver, Spencer Krieger, Tayyebeh Panahi “IC separations of pharmaceuticals and anions” National Chemistry Week Poster Session, BYU, Provo, Utah October 24, 2014.
• Jones, Chad A.; Cardinal, Jordan. “Infrared Multiphoton Dissociation Spectroscopy of Protonated Diamines in the Gas Phase.” Talk presented at the 2013 Lake Arrowhead Conference on Ion Chemistry and Mass Spectrometry; Lake Arrowhead, California; Jan. 18—20, 2013.
• Jones, Chad A. “A Conformational Study of Terminal Diamines in the Gas Phase.” Poster presented at the 2013 Gordon Research Conference on Gaseous Ions: Structures, Energetics, & Reactions; Galveston, TX; Feb. 24—Mar. 1 2013.
• Jones, Chad A. “Infrared Multiphoton Dissociation of α,ω-Diamines: A Fundamental Study of Hydrogen Bonding.” Poster presented at the 61st ASMS Conference on Mass Spectrometry and Allied Topics; Minneapolis, MN; June 9—13, 2013.
• Jones, Chad A.; Anupriya; Yang, Fan; Mortensen, Daniel N. “Cucurbituril Characterization Using Advanced Mass Spectrometry Techniques.” Invited talk presented at the 3rd International Conference on Cucurbiturils; Canberra, Australia; Nov. 17—20, 2013.
• Jones, Chad A. “Absolute Pressure Measurements in FTICR using the CRAFTI Technique.” Poster presented at the 2014 Lake Arrowhead Conference on Ion Chemistry and Mass Spectrometry; Lake Arrowhead, California; Jan. 17—19, 2014.
• Anupriya. “Cross Sections of Gas Phase Alkylammonium-Crown Ether Complexes Using the ‘CRAFTI’ Technique.” Talk presented at the 2014 Lake Arrowhead Conference on Ion Chemistry and Mass Spectrometry; Lake Arrowhead, California; Jan. 17—19, 2014.
• Anupriya. “Collision Cross Sections Using Fourier Transform Ion Cyclotron Resonance Mass Spectrometry: Applications to Supramolecular Systems.” Poster presented at the 62nd ASMS Conference on Mass Spectrometry and Allied Topics; Baltimore, MD; June 15—19, 2014.
• Jones, Chad A. “Absolute Pressure in FTICR/MS Using ‘CRAFTI’ Technique for Measuring Collision Cross Sections.” Talk presented at the 62nd ASMS Conference on Mass Spectrometry and Allied Topics; Baltimore, MD; June 15— 19, 2014.

Papers

• T. Panahi, D. J. Weaver, J. D. Lamb, R. G. Harrison “Separation of Uremic Toxins from Urine with Resorcinarene-based Ion Chromatography Columns” J. Chromatogr. A, 2015, accepted.
• Y. Lee, H. G. Koo, S. P. Jang, A. B. Erdmann, S. S. Vernetti, C. Kim, and R. G. Harrison “Synthesis of a Zn-salen Resorcinarene-based Cavitand and its Fluorescence Response to Nitro Compounds” Supramolecular Chem.2014, 26, 245-250.
• N. Li, R. G. Harrison, J. D. Lamb “Application of resorcinarene derivatives in chemical separations” J. Incl. Phenom. 2014, 78, 39-60.
• N. Li, L. J. Allen, R. G. Harrison, J. D. Lamb “Transition metal cation separations with resorcinarene-based amino acid stationary phase” Analyst, 2013, 138, 1467- 1474.
• Yang, F.; Dearden, D. V. “Effects of Kinetic Energy and Collision Gas in Measurement of Cross Sectional Areas by Fourier Transform Ion Cyclotron Resonance,” Int. J. Mass Spectrom. 2015, accepted and in press, doi: 10.1016/j.ijms.2014.07.026.
• Yang, F.; Jones, C. A.; Selvapalam, N.; Ko, Y. H.; Kim, K.; Dearden, D. V. “Binding of α,ω-Alkyldiammonium Ions by Cucurbit[n]urils in the Gas Phase,” Supramol. Chem. 2014, 26, 684-691.
• Jones, C. A.; Dearden, D. V. “Linewidth Pressure Measurement: a New Technique for High Vacuum Characterization,” J. Am. Soc. Mass Spectrom. 2015, accepted and in press, doi: 10.1007/s13361-014-1031-8.
• Anupriya; Jones, C. A.; Dearden, D. V.”Collision Cross Sections for 20 Protonated Amino Acids: Fourier Transform Ion Cyclotron Resonance and Ion Mobility Results.” J. Am. Soc. Mass Spectrom., submitted and under revision.

Description of the results/findings of the project

Several new resorcinarene-based supramolecular host molecules were synthesized, characterized, and applied to chromatographic columns where they were used for chemical separations. A new method for measuring molecular sizes (collision cross sections) in a Fourier transform mass spectrometer was developed and characterized, and a new method for measuring low pressures (needed for the cross section measurements) was also invented.

Description of how the budget was spent

The budget was spent primarily for student wages, with small amounts used to purchase chemical reagents, solvents, and other supplies.