Self-Organization of Bolaamphiphile Bearing Biphenyl Mesogen and Aspartic-Acid Headgroups

Abstract

A novel bolaamphiphile (DCBP-10-L-Asp) that bears the biocompatible aspartic acid as hydrophilic heads has been designed and synthesized. It is found that DCBP-10-L-Asp can self-organize into supramolecular fiber-like structures in aqueus solution. These fiber-like structures have a good thermal stability that can bear a temperature as high as 110 °C, because of the collective interaction, including hydrogen bonding, π-π interaction, and van der Waals interaction. The hydrogen bonding is indispensable to the formation of the supramolecular fiber-like structures, which is confirmed by adding urea or Cu 2+ ion into the solution or by changing the pH of the solution to break the hydrogen bonding. It is anticipated that this line of research may provide a way to fabricate biocompatible nanomaterials.

Tuning the Amphiphilicity of Building Blocks: Controlled Self‐Assembly and Disassembly for Functional Supramolecular Materials

“…As expected, at pH 6, the terminal groups were in acid form and the amphiphiles could also form stable fiber-like aggregates through the intermolecular p-p interaction and hydrogen-bond interaction. [66] When the pH was increased to 8.6 by the addition of potassium hydroxide, the transformation from fiber to irregular aggregates took place. Moreover, when the terminal deprotonic carboxyl groups were chelating with Cu 2þ , spherical aggregates could be effectively obtained.…”

Aggregation behavior of an amino acid-derived bolaamphiphile and a conventional surfactant mixed system

“…We will now recombine the information to propose a possible evolution of microstructure with the variation of the ratio C DTAB /C H2D . Those supramolecular structures for the H 2 D/DTAB system are common to a number of amphiphilies with large head groups that can form intermolecular hydrogen bonding [2,8,10,35]. During the aggregation process, variation of intermolecular interaction, such as hydrophobic interaction, hydrogen bonding, and p-p interactions could influence the arrangement of molecules in the aggregates, and then affect the molecular packing parameter P, resulting in microstructures with different morphologies finally.…”

“…Amino acid-derived bolaamphiphile, in particular, seem to have the additional potential of being biologically and environmentally amiable [2,10,11]. Histidine is an extremely interesting molecule in addition to its important biological properties [12][13][14][15].…”

Preparation of few‐layer two‐dimensional polymers by self‐assembly of bola‐amphiphilic small molecules

“…However, of all the papers that reported the self‐assembly of these amphiphilic molecules, only a few BASM accidentally formed 2D structures . In most cases, the resulting assemblies were zero‐dimensional or one‐dimensional structures, such as spherical micelles and fibers . In general, when the packing parameters (which represent the ability to aggregate between adjacent molecules) of amphiphilic molecules were small, it was easy to obtain zero‐dimensional or one‐dimensional structures.…”

“…[29][30][31] In most cases, the resulting assemblies were zero-dimensional or one-dimensional structures, such as spherical micelles and fibers. [32][33][34][35][36][37][38][39][40][41] In general, when the packing parameters (which represent the ability to aggregate between adjacent molecules) of amphiphilic molecules were small, it was easy to obtain zero-dimensional or onedimensional structures. When the stacking parameters were large, it was easy to form a 2D plane structure.…”