Student Project Abstracts 2005 - Pluto - University of Washington

SYNTHESIS OF A POLYENE EO CHROMOPHORE: USING A DIELS-ALDER REACTION TO FORM A SIDE-CHAIN STRUCTUREe poling voltageg at 50 C. Thever time as thedication of whenreaches a localbreakdown andto the ITO).g with 100V/umhigh as 44pm/Vthe less efficientch a side-chainFig. 4. Current Vs. Time.dication that theTable 4. Current vs. Timeity of the systemrent at such high temperatures (4.5 uA at 160 C)etween the polymer and the chromophores, whichain structure.Sample Field (V/um) Temp (‘C) Current (uA) r 33(pm/V)#1 100.00 160 4.5 42#2 100.00 110 58 35('C) Current (uA) r 33 (pm/V)0 4.5 Table 1. r4233values.#3 100.00 111 45 44CONCLUSIONIt has been shown that a highly efficient 6 of polyene 7 chromophorecan be functionalized with a dienophile. A feat that waspreviously unachievable. Furthermore, the resulting compoundcan be incorporated into a side-chain polymer via Diels-Alder“Click Chemistry” and efficient poling has been achieved in thispolymer system resulting in a reasonable r 33value.Improvements in long-term stability compared to the guesthoststructure are yet to be shown for such a system, but previousinvestigations of Diels-Alder based side-chain structures withother chromophores is promising.ACKNOWLEDGEMENTSResearch support is gratefully acknowledged from the NationalScience Foundation Center on Materials and Devices forInformation Technology Research (CMDITR), DMR-0120967.REFERENCES[1] J. Luo, M. Haller, H. Li, T.-D. Kim, A. K.-Y. Jen, Adv. Mater.2003, 15, No. 19.[2] Francesco Fringuelli and Aldo Taticchi, The Diels-Alder Reaction:Selected Practical Methods. John Wiley & Sons: 2002.[3] P. Gunter (Ed.), Nonlinear Optical Effects and Materials.Springer-Verlag: New York, 2000. (p. 197)[4] Hoyt and Benicewicz. Poly. Sci. Part A: Poly. Chem. 1990,v. 28, p. 3403.98 CMDITR Review of Undergraduate Research Vol. 2 No. 1 Summer 2005