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Boramidine: a Versatile Structural Motif for the Design of Fluorescent Heterocycles.

TitleBoramidine: a Versatile Structural Motif for the Design of Fluorescent Heterocycles.
Publication TypeJournal Article
Year of Publication2020
AuthorsLebedev, YN, Apte, C, Cheng, S, Lavigne, C, Lough, A, Seferos, DS, Aspuru-Guzik, A, Yudin, AK
JournalJ Am Chem Soc
Date Published2020 Jun 30
ISSN1520-5126
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.

DOI10.1021/jacs.0c05410
Alternate JournalJ. Am. Chem. Soc.
PubMed ID32602711