"2,7-Diazapyrenium dications combine luminescence properties similar to those of pyrene, redox properties and photoactivity similar to those of viologens, and intercalation properties very similar to those encountered in nucleic acid intercalators. It has been further proposed that 2,7-diazapyrenium dications arc attractive subunits for incorporation into macrocyclic structures in order to make photo- and electroactive receptors. In this realm, it has been demonstrated that 2,7-diazapyrenium dications can function as redox-dependent receptors for aromatic carboxylates, and therefore can find applications as electrochemical sensors. Finally, 2,7-diazapyrenium cations, when appropriately derivatized with trimethoxysilyl groups, can covalently bond to silica aerogels, and the derived luminescent materials have shown sensitivity to oxygen.
Traditional methods for the synthesis of 2,7-diazapyrenium compounds, involve oxidation of l,3,6,8-tetrahydro-2,7-dimethyl-2,7-diazapyrene either with Se or 10% Pd/C in high temperature melts. Both methods are cumbersome, but the selenium method is also potentially hazardous. The oxidation with 10% Pd/C catalyst, is low yield, and the crude product requires extensive purification.
This project resulted in the development of new methodology for the rapid, convenient, inexpensive and high yield synthesis of 2,7-diazapyrene and 2,7- diazapyrenium dications, such as the A,A"-bis(2-propenyl)-2,7-diazapyrenium quaternary salts, and their spectroscopic characterization, including absorption, time-resolved emission, and X-ray analysis"--Abstract, page iv.
Morosoff, Nicholas C.
M.S. in Chemistry
University of Missouri--Rolla
Journal article titles appearing in thesis/dissertation
- A convenient synthesis and spectroscopic characterization of N,N'-bis(2-propenyl)-2,7-diazapyrenium quaternary salts
- A facile synthesis of 2,7-diazapyrene
xi, 74 pages
© 2000 Zhan Mao, All rights reserved.
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Mao, Zhan, "Synthesis and spectroscopic characterization of 2,7-diazapyrenium compounds" (2000). Masters Theses. 1945.
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