Chiral second harmonic generation (C-SHG) has been used for the label-free detection of (R)-(+)-1,1′-bi-2-naphthol (RBN) and (S)-(+)-1,1′-bi-2-naphthol (SBN) binding to planar-supported lipid bilayers of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphotidylcholine (POPC) based on the intrinsic chirality of the molecules. C-SHG adsorption isotherms of RBN and SBN reveal Langmuir adsorption behavior with binding constants of 2.7 ± 0.2 × 10<sup>5</sup> M<sup>−1</sup> and 3.0 ± 0.1 × 10<sup>5</sup> M<sup>−1</sup>, respectively. The kinetics of RBN binding to a POPC bilayer was also measured. It was determined that the adsorption rate for RBN was 5.7 ± 0.4 × 10<sup>3</sup> s<sup>−1</sup>M<sup>−1</sup> and the desorption rate was 2.1 ± 0.8 × 10<sup>−2</sup> s<sup>−1</sup>. From the kinetic data a binding constant of 2.7 ± 1.0 × 10<sup>5</sup> M<sup>−1</sup> was calculated, which agrees well with the thermodynamic measurement. The C-SHG technique was correlat- ed with surface tension measurements in order to determine the RBN surface excess within the POPC membrane. The maximum surface excess of RBN in a monolayer of POPC was 4.3 ± 0.5 × 10<sup>−11</sup> mol cm<sup>2</sup>. Using the maximum surface excess in conjunction with the C-SHG binding data a lower limit of detection of 1.5 ± 0.1 × 10<sup>−13</sup> mols cm<sup>−2</sup>was calculated. The results of these studies show that C-SHG is a powerful tool for the study of chiral molecular interactions at surfaces.

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