Lehuta, Keith A.

Roesner, Faculty Advisor, Rebecca

Digital Commons @ Illinois Wesleyan University

Illinois Wesleyan UniversityDigital Commons @ IWUJohn Wesley Powell Student ResearchConference 2010, 21st Annual JWP ConferenceApr 10th, 9:00 AM - 10:00 AMSynthesis of a Thirty Member Macrocycle For Usein Host-Guest ChemistryKeith A. LehutaIllinois Wesleyan UniversityRebecca Roesner, Faculty AdvisorIllinois Wesleyan UniversityFollow this and additional works at: http://digitalcommons.iwu.edu/jwprcPart of the Chemistry CommonsThis Event is brought to you for free and open access by The Ames Library, the Andrew W. Mellon Center for Curricular and FacultyDevelopment, the Office of the Provost and the Office of the President. It has been accepted for inclusion in Digital Commons @ IWU bythe faculty at Illinois Wesleyan University. For more information, please contact digitalcommons@iwu.edu.©Copyright is owned by the author of this document.Keith A. Lehuta and Rebecca Roesner, Faculty Advisor, "Synthesis of a Thirty Member Macrocycle For Use in Host-GuestChemistry" (April 10, 2010). John Wesley Powell Student Research Conference. Paper 19.http://digitalcommons.iwu.edu/jwprc/2010/posters/19THE JOHN WESLEY POWELL STUDENT RESEARCH CONFERENCE APRIL 2010 Poster Presentation P29 SYNTHESIS OF A THIRTY MEMBER MACROCYCLE FOR USE IN HOST-GUEST CHEMISTRY Keith A. Lehuta and Rebecca Roesner* Chemistry Department, Illinois Wesleyan University Host-guest chemistry is the study of non-covalent interactions between container molecules and their neutral or ionic guests. Host-guest chemistry has applications in the pharmaceutical and frangrance industries and in the development of chemical sensors. The host-guest chemistry of interest in this study is that between polyoxometalate guests and azamacrocyclic hosts. A polyoxometalate is large polyatomic anion composed of early transition metal atoms, oxygen atoms, and sometimes heteroatoms. In this work, a thirty-membered macrocycle, that contains amine groups (Figure 1) is being prepared as a host for polyoxometalate guests. The two part synthetic strategy employed was first reported by Korendovych et. al for a related macrocycle. Under neutral conditions, the amine groups of the macrocycle will be able to interact with the polyoxometalate through ion-dipole forces. Under acidic conditions, the amine groups would be protonated, and the resulting ammonium groups would interact with the polyoxometalate through ion-ion forces. Figure 1 

Synthesis of a Thirty Member Macrocycle For Use in Host-Guest Chemistry

Illinois Wesleyan UniversityDigital Commons @ IWUJohn Wesley Powell Student ResearchConference 2011, 22nd Annual JWP ConferenceApr 9th, 9:00 AM - 10:00 AMSynthesis of a Thirty Member Macrocycle for Usein Host-Guest ChemistryKeith A. LehutaIllinois Wesleyan UniversityRebecca Roesner, Faculty AdvisorIllinois Wesleyan UniversityFollow this and additional works at: http://digitalcommons.iwu.edu/jwprcPart of the Chemistry CommonsThis Event is brought to you for free and open access by The Ames Library, the Andrew W. Mellon Center for Curricular and FacultyDevelopment, the Office of the Provost and the Office of the President. It has been accepted for inclusion in Digital Commons @ IWU bythe faculty at Illinois Wesleyan University. For more information, please contact digitalcommons@iwu.edu.©Copyright is owned by the author of this document.Keith A. Lehuta and Rebecca Roesner, Faculty Advisor, "Synthesis of a Thirty Member Macrocycle for Use in Host-GuestChemistry" (April 9, 2011). John Wesley Powell Student Research Conference. Paper 15.http://digitalcommons.iwu.edu/jwprc/2011/posters/15THE JOHN WESLEY POWELL STUDENT RESEARCH CONFERENCE APRIL 2011 Poster Presentation P29 SYNTHESIS OF A THIRTY MEMBER MACROCYCLE FOR USE IN HOST-GUEST CHEMISTRY Keith A. Lehuta and Rebecca Roesner* Chemistry Department, Illinois Wesleyan University Polyamine and mixed polyamine/polyamide macro cycles have been widely used ashosts for anion recognition. Although numerous cyclic and polycyclic hosts for halides, sulfates, phosphates, and carboxylates have been described, few macrocycles large enough for polyoxometalate binding are readily available. A polyoxometalate is large polyatomic anion composed of early transition metal atoms, oxygen atoms, and sometimes heteroatoms. In this work, a thirty-membered macro cycle that contains amine groups (Figure 1)  is being prepared as a host for polyoxometalate guests. The two part synthetic strategy being employed makes use of high dilution techniques and was first reported by Korendovych et. al for a related macrocycle. Under neutral conditions, the amine groups of the macrocycle may be able to interact with the polyoxometalate through ion-dipole forces and/or hydrogen bonds. Under acidic conditions, the amine groups would be protonated, and the resulting ammonium groups may interact with the polyoxometalate through ion-ion forces and/or hydrogen bonds. o /\ /\ /\  NH � N HN Figure 1 