Push-pull systems have a variety of applications in photonic devices. In this work, we designed and synthesized tetrazole-based push-pull molecules, the 1-alkyl-3-(5-aryl-2H-tetrazolyl) pyridinum and 1-alkyl-4-(5-aryl-2H-tetrazolyl) pyridinum salts, and investigated their absorption and fluorescence characteristics to evaluate their scope in organic materials. A C-N coupling reaction of phenyl tetrazole with 3-pyridyl and 4-pyridyl boronic acid in the presence of copper(I) oxide and oxygen atmosphere in DMSO at 100 oC yielded the 3-(5-phenyl-2H-tetrazol-2-yl) pyridine and 4-(5-phenyl-2H-tetrazol-2-yl) pyridine. The latter were methylated upon reaction with methyl tosylate to form the 1-methyl-3-(5-phenyl-2H-tetrazol-2-yl) pyridinium and 1-methyl-4-(5-phenyl-2H-tetrazol-2-yl) pyridinium salts, respectively. The absorption and emission spectra of the synthesized compounds was obtained in water, methanol, ethanol and dimethyl sulfoxide. The UV-Vis bands were found to be not dependent on the solvent. Time dependent density functional calculations were employed to determine the nature of electronic transitions, and our data shows that UV bands are composed of π to π* transitions.

Synthesis of push-pull tetrazoles and investigation of their spectroscopic properties

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.