Impact of molecular structure on intermolecular interactions and organic solid state luminescence in supramolecular systems

Supramolecular chemistry provides a versatile approach to tune organic solid state luminescence by controlling the molecular organization through weak interactions. In this study, we have successfully tuned the solid state luminescence of 2-cyano-3(4-(diphenylamino) phenyl) acrylic acid (CDPA) by co-crystallizing with substituted pyridines. The position of methyl group on the pyridine (4-picoline, 3-picoline, and 2-picoline) has a dramatic effect on the supramolecular interactions formed, from usual carboxylic acid-pyridine interactions to deprotonation of CDPA in the crystal lattice and that allows to tune the CDPA solid state luminescence from 587 to 548nm gradually. Copyright (C) 2010 John Wiley & Sons, Ltd.