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Amphiphilic donor-acceptor meso-ethynyl porphyrins with polar pyridinium electron-acceptor head groups and hydrophobic dialkyl-aniline electron donors have high molecular hyperpolarizabilities (as measured by hyper-Rayleigh scattering) and high affinities for biological membranes. When bound to water droplets in dodecane, or to the plasma membranes of living cells, they can be used for second harmonic generation (SHG) microscopy; an incident light of wavelength 840 nm generates a strong frequency-doubled signal at 420 nm. Copper(II) and nickel(II) porphyrin complexes give similar SHG signals to those of the free-base porphyrins, while exhibiting no detectable two-photon excited fluorescence.

Original publication

DOI

10.1021/ja8061369

Type

Journal article

Journal

J Am Chem Soc

Publication Date

04/03/2009

Volume

131

Pages

2758 - 2759

Keywords

Cell Line, Tumor, Copper, Humans, Membrane Lipids, Metalloporphyrins, Microscopy, Fluorescence, Nickel, Porphyrins, Scattering, Radiation