Schiff-base supported heterobicyclic monomeric boronates

•Condensation of Schiff base with arylboronic acids.•Synthesis of boronate-imine complexes.•Characterization of boronates by standard analytical methods and single crystal X-ray diffraction.•Absorption and emission properties.

Four monomeric boronates 1a–1b and 2a–2b have been synthesized in a single step reaction. Complex 1a was obtained from a reaction of Schiff base ligand, N-(2-hydroxyphenyl)-3-methoxy-salicylideneamine (H2L) and phenylboronic acid in methanol. However, complexes 1b, 2a and 2b were synthesized by reacting o-vanillin with 2-amino phenol or 2-amino-4-nitrophenol and phenylboronic acid or 4-flurophenylboronic acid in a single step reaction in acetonitrile respectively. All complexes have been characterized by NMR spectroscopy, IR spectroscopy, elemental analyses and mass spectrometry. The solid state structures of two complexes 1a and 2a were determined by single crystal X-ray diffraction analysis. The solid state structures confirm the formation of boronate complexes in 1a and 2a. The optical properties of all complexes have been explored.

Graphical abstractFour boronates with a B–N dative bond have been synthesized and characterized. All complexes show [4.3.0] heterobicyclic structures. Absorption and emission properties of all complexes have been investigated.Figure optionsDownload full-size imageDownload as PowerPoint slide