Solution- and solid-phase synthesis of components for tethered bilayer membranes.

Area of Science:

• Biomaterials Science
• Organic Chemistry
• Surface Chemistry

Background:

• Tethered bilayer membranes are crucial for mimicking biological membranes.
• Previous ester-containing compounds have shown promise in membrane formation.
• Developing all-amide analogues offers alternative material properties.

Purpose of the Study:

• To synthesize a novel all-amide compound for tethered bilayer membrane preparation.
• To compare the properties of the new all-amide compound with existing ester-containing analogues.
• To characterize the self-assembly behavior of the novel compound on gold surfaces.

Main Methods:

• Synthesis of the all-amide compound PhCH(2)SS(C(24)H(44)N(4)O(10))(C(20)H(41)) (5).
• Preparation of an advanced intermediate using both solution-phase and solid-phase techniques.
• Analysis of self-assembled monolayers on gold using ellipsometry and Fourier-transform infrared spectroscopy (FTIR).

Main Results:

• The novel all-amide compound (5) was successfully synthesized.
• Solid-phase synthesis yielded a significantly higher intermediate yield (81%) compared to solution-phase (13%).
• Monolayers formed from compound 5 exhibited comparable thicknesses to ester analogue monolayers and displayed characteristic H-bonded amide functionality.

Conclusions:

• The novel all-amide compound is a viable alternative for creating tethered bilayer membranes.
• Solid-phase synthesis offers an efficient route for preparing key intermediates.
• The self-assembled monolayers demonstrate functional H-bonding, suggesting potential for biomimetic applications.