Use of Unprecedented Intramolecular 1, 3-Dipolar Cycloaddition Reaction in meso-Nitrile Oxide-Containing BODIPYs as a New Pathway for the Preparation of Fused NIR Platforms

Authors

• Nikolay N. Gerasimchuk, Missouri State UniversityFollow
• Yuriy V. Zatsikha, University of Manitoba;Taras Shevchenko National University of Kyiv
• Dijo Prasannan, The University of Tennessee, Knoxville
• Briana Scharge, The University of Tennessee, Knoxville
• David E. Herbert, University of Manitoba
• Mattias Zeller, College of Science
• Victor N. Nemykin, The University of Tennessee, Knoxville

Abstract

Meso-nitrile oxide group in 1,7-Diphenyl-containing BODIPYs can be involved in highly unusual [3+2] intramolecular cycloaddition reaction with the formation of the dihydrobenzo[d]isoxazole-containing BODIPYs. Oxidation of these compounds results in the formation of unprecedented either benzisoxazole- or benzo[b]azepine-fused fully conjugated NIR absorbing BODIPYs. The photophysical properties and electronic structures of the target compounds were studied by an array of experimental and theoretical methods.

Department(s)

Chemistry and Biochemistry

Document Type

Article

DOI

10.1002/chem.202401210

Keywords

BODIPY, NIR dyes, nitrile oxide, [3+2] cycloaddition

Publication Date

6-20-2024

Recommended Citation

Gerasimchuk, Nikolay N.; Zatsikha, Yuriy V.; Prasannan, Dijo; Scharge, Briana; Herbert, David E.; Zeller, Mattias; and Nemykin, Victor N., "Use of Unprecedented Intramolecular 1, 3-Dipolar Cycloaddition Reaction in meso-Nitrile Oxide-Containing BODIPYs as a New Pathway for the Preparation of Fused NIR Platforms" (2024). Faculty Scholarship. 353.
https://bearworks.missouristate.edu/articles00/353

Journal Title

Chemistry A European Journal