Issue 7, 2016

Synthesis and spectroscopic properties of novel N–N linked bis-(diphenylboron) complexes

Abstract

Novel five-membered-ring and six-membered-ring bis-(diphenylboron) complexes, consisting of hydrazine-Schiff base linked bispyrrole and two phenyl rings on the boron atoms, are readily synthesized via a facile two-step reaction. Weak intermolecular interactions are observed in the solid-state X-ray crystal structures due to the replacement of fluorine with a phenyl group at the boron atom. Both complexes exhibit high fluorescence in dilute solutions with quantum efficiencies in the range of 0.52–0.88. Because of weak intermolecular interactions and a large Stokes shift, the six-membered-ring complex 1 exhibits efficient solid-state fluorescence. However, the five-membered-ring complex 2 has a small Stokes shift, resulting in weak fluorescence in the solid-state through self-quenching. The structure–property relationships have been analyzed on the basis of X-ray crystallography, optical spectroscopy, and theoretical calculations.

Graphical abstract: Synthesis and spectroscopic properties of novel N–N linked bis-(diphenylboron) complexes

Supplementary files

Article information

Article type
Paper
Submitted
15 Nov 2015
Accepted
08 Feb 2016
First published
08 Feb 2016

New J. Chem., 2016,40, 5752-5757

Author version available

Synthesis and spectroscopic properties of novel N–N linked bis-(diphenylboron) complexes

L. Gai, J. Xu, Y. Wu, H. Lu and Z. Shen, New J. Chem., 2016, 40, 5752 DOI: 10.1039/C5NJ03217B

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