Issue 2, 2022

Bis-isonicotinoyl linkers containing polyaromatic scaffolds: synthesis, structure and spectroscopic properties

Abstract

In this study, a new series of extended linkers containing different polyaromatic chromophores (biphenyl, naphthalene, anthracene, fluorene, 9,9-dimethylfluorene and fluorenone) functionalized with isonicotinoyl moieties have been synthesized by Pd-catalyzed cross-coupling reactions involving isonicotinamide and the appropriate aromatic dibromide. The optimized protocol led to the isolation of the target molecules in good yield and with high purity. These were characterized by 1H NMR, FTIR, MS, and elemental analysis and their solid state structures were solved by single-crystal X-ray diffraction analysis. Electronic absorption and emission spectra were collected both in solution (DMF) and in the solid state. TDDFT calculations were carried out to investigate the effect of the isonicotinoyl moieties on the spectral features of the central chromophores. Although in solution only the linker containing a fluorenone scaffold shows a weak fluorescence, all the isolated linkers turned out to be fluorescent in the solid state, thus paving the way for their use for the fabrication of fluorescent MOFs.

Graphical abstract: Bis-isonicotinoyl linkers containing polyaromatic scaffolds: synthesis, structure and spectroscopic properties

Supplementary files

Article information

Article type
Paper
Submitted
27 Sep 2021
Accepted
01 Dec 2021
First published
03 Dec 2021

Phys. Chem. Chem. Phys., 2022,24, 1191-1201

Bis-isonicotinoyl linkers containing polyaromatic scaffolds: synthesis, structure and spectroscopic properties

A. Delledonne, M. Orlandini, P. P. Mazzeo, C. Sissa, A. Bacchi, F. Terenziani and P. Pelagatti, Phys. Chem. Chem. Phys., 2022, 24, 1191 DOI: 10.1039/D1CP04438A

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