Synthesis and characterization of terpene-derived cationic bolaamphiphiles

Abstract

Terpenes represent an abundant and sustainable feedstock for the construction of functional organic materials. Utilizing either trans-β-farnesene or myrcene as starting materials, we have developed a three-step synthetic sequence leading to a new class of terpene-containing cationic bolaamphiphiles. Two of the synthetic steps are devoid of solvent and proceed in reasonably high yield. The final step, a photochemical thiol-ene reaction, transforms a wholly hydrophobic precursor into a segmented amphiphilic molecule. The implementation of a late-stage thiol-ene reaction creates new opportunities for the introduction of chemical diversity into terpene-containing compounds and assemblies. The ease of synthesis combined with the versatility of the thiol-ene late stage functionalization opens-up a large design space and creates opportunities in a wide variety of areas including gene delivery, surfactants, and antimicrobials.