Observation of entanglement between two light beams spanning an octave   in optical frequency
  We have experimentally demonstrated how two beams of light separated by an octave in frequency can become entangled after their interaction in a second-order nonlinear medium. The entangler consisted of a nonlinear crystal placed within an optical resonator that was strongly driven by coherent light at the fundamental and second-harmonic wavelengths. An inter-conversion between the fields created quantum correlations in the amplitude and phase quadratures, which were measured by two independent homodyne detectors. Analysis of the resulting correlation matrix revealed a wavefunction inseparability of 0.74(1) < 1 thereby satisfying the criterion of entanglement. 
Nicolai B. Grosse, Syed Assad, Moritz Mehmet, Roman Schnabel, Thomas   Symul and Ping Koy Lam