Control of self-assembly of a 3-hexen-1,5-diyne derivative: Toward soft materials with an aggregation-induced enhancement in emission

The supramolecular architectures of a fluorophore are controlled through the design of a conjugated polycatenar molecule, the self-assembly of which can be addressed toward a columnar liquid-crystalline phase and organogels. Thus, depending on the environmental conditions for self-assembly, compound CA9 organizes into an unprecedented hexagonal columnar mesophase in the condensed state, in which half a molecule constitutes the slice of the column, or into a rectangular mesomorphic-like organization in the presence of apolar solvents such as cyclohexane and dodecane, at a concentration in which fibers form and gelling conditions are fulfilled. In this Colr-type arrangement, the organization within the columns depends on the solvent. All of the materials prepared show luminescence, and moreover, a remarkable 3-fold increase in fluorescence intensity was observed in going from the solution to the gel state. © 2011 American Chemical Society.This work was supported by the MICINN (Projects MAT2009-14636-C03-01, CSD2006-00012, and CTQ-2007- 61048), FEDER funding (EU), the Aragon Government, and Principado Asturias (Project IB08-088).Peer Reviewe