Synthesis, Structure and Photophysical Properties of 1,8-Naphthalimidyl-Derived Schiff Base and Its Boron Complex

Abstract

A novel Schiff base containing 1,8-naphthalimidyl group (L) and its boron complex C27H29BN4O2F2 (I) were successfully synthesized and their structures were confirmed by using elemental analysis, UV−Vis, ESI-MS, 1H NMR and 13C NMR spectroscopies. The fluorescence properties of new Schiff base L as well as its boron complex I were investigated. X-ray single crystal analysis of boron complex I (CIF file CCDC no. 1888435) reveals that the coordination of BF2 with one of the hydrazone group nitrogens (N(2)) along with the pyridyl nitrogen (N(3)) forms a six-membered ring. The boron atom adopts a tetrahedral geometry and the plane defined by F–B–F atoms is perpendicular to that of the central C(2)N(3) core. One-dimensional chains were formed along the b axis through weak π–π interactions and the adjacent molecular are stabilized by C–H⋅⋅⋅O hydrogen bonds interactions, forming a three-dimensional architecture. Luminescent properties reveal that the emission wavelength is blue-shifted whether in CH2Cl2 solution or in crystal state after the ligand was coordinated by BF2 fragment. The Stokes shift for I is about 73 nm, which may have been caused by the intramolecular hydrogen bonds dominated by the oxygen atom and the nitrogen atom and the distortion of the molecular structure.

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Funding

We appreciate the financial support from Shandong Provincial Natural Science Foundation (ZR2018LB015); the Scientific Research Foundation of Qingdao Agricultural University.

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Correspondence to L. B. Gao.

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Gao, L.B. Synthesis, Structure and Photophysical Properties of 1,8-Naphthalimidyl-Derived Schiff Base and Its Boron Complex. Russ J Coord Chem 47, 88–94 (2021). https://doi.org/10.1134/S1070328420120039

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Keywords:

  • Schiff base
  • boron complex
  • crystal structure
  • fluorescence properties