Cyclic tri-β-peptide having tetrathiafulvalene (TTF) at the side chain was synthesized to prepare a peptide nanotube aligning TTF side chains along the nanotube. The polarized light microscopic observations revealed crystallization of the cyclic peptide by the vapor diffusion method. Fourier-transform infrared and electron diffraction measurements of the crystals clarified formation of homogeneous hydrogen bonds making a columnar structure with a layer spacing of 4.9 Å. Electronic measurements of the peptide crystals on a gold mica substrate were carried out by the current sensing AFM. The current-voltage curves showed a rectification behavior, whose profile was consistent with a metal and p-type semiconductor junction. The p-type property is supported by the first principle calculations, which showed the HOMO orbital delocalizing fully over the plane of the TTF ring with the energy level of -5.1 eV. © 2016 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 275-282, 2016.
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