The results of the study presented here show a new example of the use of liquid crystals and the interactions involved in the mesomorphic state to build up complex molecular organizations. We have pursued a design strategy in which hydrogen bonding allows the combination of the pi-stacking tendency of melamine and the lateral interaction capability of V-shaped molecules, which has been extensively demonstrated through nematic, smectic, or columnar mesophases. This combination addresses the formation of columnar arrangements with inherent helical organization. In this work, nonmesomorphic as well as mesomorphic V-shaped acids, with a structure similar to banana liquid crystals, have been complexed to a 2,4,6-triamino-1,3,5-triazine derivative in a proportion 3 to 1, respectively. Hydrogen-bonded supramolecules whose formation and stability in solution have been proven by infrared and NMR techniques have been thus obtained. DOSY experiments have allowed us to assess in solution the presence of the complexes and their tetrameric composition. All the complexes display mesogenic ability, and their mesomorphic organization has been studied by X-ray diffraction and CD spectroscopy. Results allow us to propose a helical columnar model for the mesophase originated from a propeller-like conformation of the supramolecular complexes.

The creation of cyclodextrin patterns on a fluorescent reporter surface by microcontact printing provides a versatile orthogonal surface modification method. The alkyne-beta-cyclodextrin surface is prepared through a "click" reaction on alkyne-terminated coumarin monolayers. The resulting alkyne-beta-cyclodextrin surface can be functionalized through supramolecular microcontact printing on cyclodextrin host patterns and by reactive microcontact printing-induced click chemistry on the alkyne-terminated patterns. The orthogonal covalent and supramolecular "host-guest" functionalization of the surface, and its specificity as well as selectivity, is demonstrated by sequential and one-step printing procedures.

The use of complementary 2,4,6-triarylamino-1,3,5-triazines and benzoic acids has allowed the preparation of a variety of disklike supramolecules with different substitution patterns around an H-bonded aromatic core. Most of the complexes obtained show columnar mesomorphism promoted by an efficient columnar packing of the aromatic cores surrounded by a minimum of six peripheral tails. The steric requeriments for the appearance of mesomorphic behavior in these supramolecular complexes have been established by X-ray diffraction studies and density calculations based on the parameters of the liquid crystalline organization.

The synthesis and photopolymerization of various liquid crystalline dioxetanes is described. The effects of the spacer length, structure of the mesogenic group and oxetane group on the liquid crystalline properties, polymerization behaviour and optical properties (birefringence) of the oriented and crosslinked network formed in photo-polymerization are discussed. Thermally stable films with birefringence values up to 0.13 can be formed from these materials. The dioxetanes show significantly lower polymerization shrinkage than do structurally related diacrylates.