Student Project Abstracts 2005 - Pluto - University of Washington

LEVIThe binary dendron system requires a single deprotection stepfollowed by a single catalytic esterification. Employing monolithicdendrons necessitate two separate deprotection reactionsand two esterifications. Furthermore, r 33measurements (seeTable 2 below) illustrate the binary dendron systems offer significantimprovements in EO activity while maintaining the thermalproperties of the monolithic dendron systems.Chromophore I. displays 100 % stability in the EO activityafter 24 hours at 75 OC; similar temporal stability is absent in materials1-4.Zerubba Levi will be graduating from Gonzaga University in thespring of 2006 with a B.S. in Chemistry. Following graduationhe intends to pursue a Ph.D. degree in Organic Chemistry.CONCLUSIONSIn summary, a series of monolithic and binary dendrons weresynthesized, and covalently attached to highly efficient NLOchromophores. The primary motivation of this work is fine tuningthe strengths of arene-fluoroarene interactions between dendronsto produce pre-aligned supramolecular self-assembly toimprove material stability and poling efficiencies. Anthracenewas incorporated into the dendrons in an effort to increase thenoncovalent, arene-fluoroarene interactions between dendrons.While the presence of anthracene increased the thermal stabilityof the materials, it is unclear for now whether the replacement ofthe phenyl ring with anthracene leads to stable pre-alignment orimproved poling efficiency. However, the binary dendron systemsshow significantly improved EO activities relative to previousmonolithic dendron systems studied. The basis for thisimprovement will be further studied. Full characterization ofstructures and material properties are ongoing.REFERENCES1. Patrick, C. R.; Prosser, G. S. Nature 1960, 187, 1021.2. Collings, J. C.; Roscoe, K. P.; Robins, E. G.; Batsanov, A. S.;Stimson, L. M.; Howard, J. A.; Clark, S. J.; Marder, T. B. New J.Chem. 2002, 26, 1740-1746.3. Castellano, R. K.; Diederich, F.; Meyer, E. A. Angew. Chem.Int. Ed. 2003, 42, 1210-1250.ACKNOWLEDGEMENTSMany thanks are given to Tae-Dong Kim, and Zhengwei Shifor helpful discussions and important synthetic intermediates,Steve Hau for sample poling and r 33measurements, and the NSFSTC-MDITR 2005 Summer REU Program for funding.CMDITR Review of Undergraduate Research Vol. 2 No. 1 Summer 2005 69