|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|
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.
|Alternate Journal||J. Am. Chem. Soc.|