Synthesis and Characterization of Lipophilic, Near-IR Absorbing Metallobacteriochlorins

doi:10.7503/cjcu20120865

Abstract

Abstract:

The metalation of bacteriochlorins, an ostensibly simple reaction, has proved more difficult than the metalation of porphyrins and chlorins. The traditional synthesis method to prepare metalloporphyrins(metal acetate in heated N,N-dimethyl formamide) is not generally applied to the synthesis of metallobacteriochlorins. In this paper, by treating bacteriochlorins 3,13-bis(ethoxycarbonyl)-2,12-diheptyl-8,8,18,18-tetramethylbacteriochlorin(HBC) or 3,13-bis(ethoxycarbonyl)-2,12-diheptyl-5-methoxy-8,8,18,18-tetramethylbacteriochlorin(MeOBC) in THF with a strong base(NaH) followed by a metal reagent MX_n(M=Ni, Cu, Pd), five new metallobacteriochlorins were obtained. The as-synthesized metallobacteriochlorins were characterized by ¹H NMR spectroscopy and mass spectrometry, and their absorption and fluorescence spectra were studied. For a bacteriochlorin, the insertion of a metal typically causes a bathochromic shift of the position of the long-wavelength absorption band. Both bacteriochlorin ligands and Zn complexes exhibit Q_y(0,0) fluore-scence, and the Cu and Ni bacteriochlorin complexes exhibit no fluorescence.

Key words: Bacteriochlorin, Metal complex, Absorption spectrum

CLC Number:

O614
O641.4

TrendMD:

SUN Er-Jun, CHEN Chih-Yuan, LINDSEY Jonathan S.. Synthesis and Characterization of Lipophilic, Near-IR Absorbing Metallobacteriochlorins[J]. Chem. J. Chinese Universities, 2013, 34(4): 776.

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