Synthesis, spectroscopic properties and theoretical calculations on methylene bridged 1,8-naphthyridine ligands and copper(I) complex through a non-catalyst C(sp3)–H methylenation

Gou, Gaozhang ; Zhou, Bo ; Chen, Xue-Bing ; Wang, Xue-Quan ; Mang, Chao-Yong ; Liu, Wei ; Chi, Shao-Ming

Abstract

Two 1,8-naphthyridine derivatives containing methylene, N-(5-methyl-7-((3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl)-1,8-naphthyridin-2-yl)acetamide (L1) and 2-amino-3-((7-amino-4-methyl-1,8-naphthyridin-2-yl)methyl)isoindolin-1-one (L2), as well as a copper(I) complex CuI(L1)2 (C1) have been synthesized through a non-catalyst C(sp3)–H methylenation process and characterized. The structure of C1 has been determined by X-ray diffraction analysis. The spectroscopic properties have been investigated by experimental as well as theoretical studies for all these compounds. The two ligands exhibit similar electronic absorption spectra with λmax at about 340 nm, which can be tentatively assigned to πnaph→πnaph* transition. The electronic absorption spectra of C1 exhibits at ~335 nm except in n-hexane, which may be assigned tentatively to the intraligand charge transfer transition. The assignment is further supported by density functional theory calculations and cyclic voltammetry.

Keyword(s)

Coordination chemistry, Density functional calculations, Metal-to-ligand charge-transfer, Crystal structure,
Spectroscopic properties, 1,8-Naphthyridine, Copper

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