Chiral ionic liquids supported on natural sporopollenin microcapsules

Supported chiral ionic liquids (SILs) were prepared choosing the starting material for the ionic liquid part from the enantiopure stock of the chiral pool (monoterpenoids and an amino acid) and the sporopollenin as an environmentally friendly support. Sporopollenins are microcapsules with naturally well-defined sizes and shapes that can be obtained from pollen grains after removal of the internal cytoplasm and the second shell layer. As thermally stable organic biocompatible structures, sporopollenins have attracted increasing interest in recent years for several applications. Herein, bio-based ILs were anchored onto the surface of sporopollenins obtained from the pollen of Populus deltoides, selected as a model pollen grain. These new structures, which present an external positively charged shell, were characterized by physico-chemical techniques (ATR-FTIR, TGA, SEM, EDX, and solid-state (13)C NMR). A metathesis reaction was also performed on selected bio-based IL modified sporopollenins, demonstrating the possibility to switch the surface properties by exploiting well-known IL chemistry.