Amphiphilic porphyrins for second harmonic generation imaging.
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.
Reeve
James E
JE
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK.
Collins
Hazel A
HA
De Mey
Kurt
K
Kohl
Michael M
MM
Thorley
Karl J
KJ
Paulsen
Ole
O
Clays
Koen
K
Anderson
Harry L
HL
D045744:Cell Line, Tumor; D003300:Copper / Q000737:chemistry; D006801:Humans; D008563:Membrane Lipids / Q000737:chemistry; D008665:Metalloporphyrins / Q000737:chemistry; D008856:Microscopy, Fluorescence / Q000379:methods*; D009532:Nickel / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry*; D012542:Scattering, Radiation
D008563:Membrane Lipids; D008665:Metalloporphyrins; D011166:Porphyrins; D003300:Copper; D009532:Nickel