bola-Type Ala-Ala Dipeptides: Odd-Even Effect in Molecular Packing Structures.

ABSTRACT

A series of bola-type Ala-Ala dipeptides with different alkylene bridges (n = 10-15) were synthesized. In methanol, the molecules with even-numbered carbon bridges self-assembled into twisted nanoribbons, while those with odd-numbered carbon bridges self-assembled into straight belts. The morphology displays a pronounced odd-even dependence upon the number of carbons (n) in the connecting alkylene bridge. The circular dichroism spectra of the self-assemblies showed that molecules with even- and odd-numbered carbon bridges stacked in different structures. FT-IR spectra indicated that the dipeptides with even-numbered carbon bridges formed hydrogen bonds between the amide group and carboxyl ester group, while those with odd-numbered carbon bridges formed hydrogen bonds only between the amide groups. X-ray diffraction patterns revealed that molecules with odd- and even-numbered carbon bridges stacked in monoclinic and triclinic structures, respectively.