New Hopf Structures on Planar Binary Trees Two of the most interesting combinatorial Hopf algebras are the Hopf algebras of permutations and of planar binary trees. These fit into an interesting commutative diagram involving the symmetric, noncommutative symmetric, and quasisymmetric functions. They also each have two different bases related by Moebius inversion on a poset which reveal a rich interaction between their algebraic structure and the combinatorics of permutations and of trees. These posets are the edge graphs of the permutahedra and the associahedra, and the algebra structure is also linked to the structure of these polytopes. Both the permutahedra and associahedra arise naturally in homotopy theory, and the point of departure for this talk is another family of polytopes, the multiplihedra, which also arose in homotopy theory. Natural cellular maps from permutahedra to associahedra (which induce maps of Hopf algebras) factor through the multiplihedra. Restricting this map to their vertices factorizes the map from permutations to trees. The intermediate objects are certain bi-leveled trees. We show how to put algebraic structures on bi-leveled trees so that their linear span M becomes a module over the Hopf algebra of permutations and a Hopf module algebra over the Hopf algebra of trees. A second basis of M, related to the first via Moebius inversion on the multiplihedra helps to elucidate these structures. Bi-leveled trees also admit a second structure as a Hopf algebra, and we identify other combinatorial objects between permutations and trees which similarly are related to polytopes and admit some Hopf structures. This is joint work with Aaron Lauve and Stefan Forcey.