Steric effect on the self-assembly behaviours of amino acid derivatives

作者：Fan Yulan; Cheng Linxiu; Liu Chunhua; Xie Yunzhi; Liu Wei; Li Yongdong; Li Xun; Li Yibao^*; Fan Xiaolin

来源：RSC Advances, 2014, 4(94): 52245-52249.

DOI：10.1039/c4ra06582d

To investigate the steric effect of amino acids, N,N'-dialanine-1,4,5,8-naphthalene tetracarboxylic acid diethylamide (ANTA) and N,N'-diphenylalanine-1,4,5,8-naphthalene tetracarboxylic acid diethylamide (PNTA) were synthesized based on naphthalene-1,4,5,8-tetracarboxylic dianhydride (NTA) with alanine and phenylalanine, respectively. These compounds were characterized by infrared spectroscopy (IR), magnetic resonance spectroscopy (H-1 NMR, C-13 NMR) and mass spectrometry (MS). Interestingly, ANTA could self-assemble into spiral nanorings, but PNTA formed nanospheres. In order to reveal the self-assembly driving forces, the two-dimensional (2D) supramolecular self-assembly behaviours were studied on highly oriented pyrolytic graphite (HOPG) by scanning tunneling microscopy (STM) at the solid-liquid interface, which indicated the driving forces could be attributed to intermolecular hydrogen-bonding and pi-pi stacking interactions. These results represent different self-assembly behaviours due to the steric effect of amino acids.

• 出版日期2014
• 单位赣南师范大学