Department Chair

M. Scott Goodman, Ph.D., Professor of Chemistry

Date of Award

8-2016

Access Control

Campus-Only Access

Degree Name

Forensic Science, M.S.

Department

Chemistry Department

Advisor

M. Scott Goodman, Ph.D., Chair and Professor of Chemistry

Department Home page

chemistry.buffalostate.edu

First Reader

William Durfee, Ph.D., Professor of Chemistry

Second Reader

Jinseok Heo, Ph.D., Associate Professor of Chemistry

Abstract

The synthesis and characterization of pyrazole-appended tetraazamacrocyclic ligands are reported. Synthesis and separation of t-butoxycarbonyl (Boc) protected 1,4,8,11-tetraazacyclotetradecane (cyclam) allows for the formation of several isomers: triboc cyclam, cis-diboc cyclam, and trans-diboc cyclam. The different isomers were then each functionalized with pyrazole arms by reaction with the corresponding equivalents of either 1-(2-bromoethyl) pyrazole or 1-(2-bromoethyl)-3,5-dimethylpyrazole. Thereafter, the protective Boc groups were removed from the compound by heating in water for an extended time to afford the unprotected macrocycles with one or two pyrazole pendant groups. The resulting ligands can potentially be further functionalized if desired. Synthesis of a structurally similar ligand, 1,8-(2-pyrazoylethyl)-Tet-A or PzTeta, was also carried out. The crystal structure of PzTeta was determined as having a monoclinic unit cell with dimensions: a = 10.2359(6) Å, b = 16.9312(11) Å, c = 15.9755(10) Å, and β = 100.17°. The 1H NMR spectra of all synthesized ligand systems show dispersed and relatively sharp proton resonances. By forming complexes of these ligands with various transition metal ions, it should be possible to prepare novel contrast enhancement agents with applications in magnetic resonance imaging.

Supporting Information M.S..docx (1401 kB)
Supplementary Material

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