Vapor phase self-assembly of electrooptic thin films via triple hydrogen bonds

The donor-acceptor π-electron chromophore 5-{4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]-benzylidene}-pyrimidine-2,4,6-trione (DTPT) was designed and synthesized. Triple H-bonding interactions between neighboring molecules direct self-assembled chromophore alignment in a head-to-tail orientation using a straightforward vapor phase deposition process. Angle-dependent SHG interference patterns and the quadratic dependence of the 532 nm light output intensity on the thickness of the DTPT films for glass substrates coated on both sides demonstrate high, reproducible film quality and uniformity. XRD also demonstrates long-range order in the film and yields a molecular tilt angle in good agreement with polarized SHG data, clearly showing that out-of-plane ordering of chromophore molecules has been achieved. Copyright © 2003 American Chemical Society.