Title | Boramidine: a Versatile Structural Motif for the Design of Fluorescent Heterocycles. |
Publication Type | Journal Article |
Year of Publication | 2020 |
Authors | Lebedev, YN, Apte, C, Cheng, S, Lavigne, C, Lough, A, Seferos, DS, Aspuru-Guzik, A, Yudin, AK |
Journal | J Am Chem Soc |
Date Published | 2020 Jun 30 |
ISSN | 1520-5126 |
Abstract | Sodium cyanoborohydride-derived N-alkylnitriliumboranes were found to be versatile precursors for the synthesis of novel boron-containing heterocycles. The reaction between N-alkylnitriliumboranes and 2-aminopyridines, -imidazoles, -oxazoles, or -isoxazoles leads to incorporation of the [B-C] motif into a five-membered boramidine which exist as a mixture of Z and E isomers. The resulting heterocycles are blue-fluorescent in both the solid state and in solution with ca. 2700 - 8400 cm-1 Stokes shifts and quantum yields in the 65 - 74% range in water and in the 42 - 84% range in organic solvents. The combination of photophysical properties, structural tunability, stability, and solubility in various media are expected to find application in a range of disciplines. |
DOI | 10.1021/jacs.0c05410 |
Alternate Journal | J. Am. Chem. Soc. |
PubMed ID | 32602711 |