Unique twisted ribbons generated by self-assembly of oligo(p-phenylene ethylene) bearing dimeric bile acid pendant groups.
Let's twist again! Remarkable broad and twisted ribbons were generated from the self-assembly of oligo(p- phenylene ethylene) (OPE) bearing dimeric deoxycholic acid pendant groups (see graphic). Varying the bile acid led to nanostructures with drastically different morphologies. The distinctive aggregate shapes of these steroid-OPE conjugates are attributed to the subtle differences in their molecular structures.A series of novel oligo(p-phenylene ethynylene) (OPE) derivatives bearing dimeric cholic acid (OPE1), deoxycholic acid (OPE2) and lithocholic acid (OPE3) was synthesized. The self-assembly behavior of these derivatives were systematically studied and compared in a THF/water solvent mixture. The addition of water to THF can induce the helical stacking of oligo(p-phenylene ethylene) bearing dimeric deoxycholic acid end groups, which leads to highly interesting twisted assemblies. Variation of the bile acid group led to nanostructures with drastically different morphologies. The application of spectroscopy in combination with X-ray diffraction techniques provided a reasonable view of the final self-assembled structures. The observed distinctive aggregate shapes and the preference in the type of molecular packing of these steroid-OPE conjugates are attributed to the subtle differences in their molecular features.
Li
Yan
Y
Department of Chemistry, Key Lab of Organic Optoelectronics & Molecular Engineering, Ministry of Education, Tsinghua University, Beijing, China.
Li
Guangtao
G
Wang
Xinyan
X
Li
Weina
W
Su
Zhixiang
Z
Zhang
Yihe
Y
Ju
Yong
Y
D000480:Alkynes / Q000737:chemistry*; D001647:Bile Acids and Salts / Q000737:chemistry*; D003840:Deoxycholic Acid / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D013053:Spectrophotometry; D014961:X-Ray Diffraction
D000480:Alkynes; D001647:Bile Acids and Salts; D004987:Ethers; C436384:phenyleneethynylene; D003840:Deoxycholic Acid