SYNTHESIS AND CHARACTERIZATION OF EXTENDED SQUARAINE COMPOUNDSScheme 4. Synthesis <strong>of</strong> the desired product, squaraine (11) using (3).Dibutyl-{4-[2-(3,4-dibutoxy-thiophen-2-yl)-vinyl]-phenyl}-amine, (7) was then treated with butyl lithium in dry THF at 0 ºC,after two hours DMF was added and left overnight all under N 2.The red solution was washed with water and extracted with ethylacetate (3×). The organic phase is collected and dried over magnesiumsulfate. The concentrated solution was purified by columnchromatography, eluent 10:1 hexanes to ethyl acetate in silica togive (8). 3,4-dibutoxy-5-[2-(4-dibutylamino-phenyl)-vinyl]-thiophene-2-carbaldehyde,(8), was reduced by sodium borohydridein ethanol, similar to the procedure for compound (5), which wasthen reacted with tri-ethyl phosphate in iodine at 0 ºC and leftovernight under N 2. Vacuum distillation was performed on thesolution for two hours and purified by column chromatography,eluent 4:1 hexanes to ethyl acetate to yield (9).Compound (3), 1-(2-ethyl-hexyl)-1H-pyrrole-2-carbaldehydewas reacted with {3,4-Dibutoxy-5-[2-(4-dibutylamino-phenyl)-vinyl]-thiophen-2-ylmethyl}-phosphonicacid diethyl ester,compound (9), in dry THF and a solution <strong>of</strong> potassium tert-butoxidein dry THF by a Horner-Emmons Condensation, underN 2,for an hour and a half. The concentrated oil was purified bycolumn chromatography, eluent 10:1 hexanes to ethyl acetate insilica to give rise to compound (10). Dibutyl-{4-[2-(3,4-dibu-toxy-5-{2-[1-(2-ethyl-hexyl)-1H-pyrrol-2-yl]-vinyl}-thiophen-2-yl)-vinyl]-phenyl}-amine, (10) is treated with squaric acid togive the desired compound (11) Squaraine.CONCLUSIONAfter several failed reactions, it was determined that an alkylatedpyrrole carbaldehyde can be synthesized in high yield.Many <strong>of</strong> these reactions caused side products which requiredcareful purification techniques that took longer than expected.Therefore, the desired product squaraine is one reaction awayfrom completion. After pure squaraine is obtained, tests will beperformed on the organic dye to determine its efficacy in producingoptical quality, thin films.REFERENCESM.J. Plater, T. Jackson. Tetrahedron 59 (2003). pages 4673-4685(page 4679).ACKNOWLEDGEMENTSResearch support is gratefully acknowledged from the NationalScience Foundation Center on Materials and Devices forInformation Technology Research (CMDITR), DMR-0120967.Tehetena Mesganaw is currently attending the Georgia Institute <strong>of</strong>Technology and majoring in Chemistry. After graduation im Fall 2006,she plans to attend graduate school and obtain her Ph.D in OrganicChemistry. From there, she plans to do research on the AIDS epidemic.82 CMDITR Review <strong>of</strong> Undergraduate Research Vol. 2 No. 1 Summer <strong>2005</strong>
Enhanced Heat Dissipation Substrates for Organic Semiconductor DevicesAaron Montgomery<strong>University</strong> <strong>of</strong> VirginiaDr. Samuel GrahamGeorgia Institute <strong>of</strong> TechnologyAshante Allen, Erik Sunden and Adam Christensen`Many electronic devices are susceptible to overheatingwhich can result in failures <strong>of</strong> the device. This can be exemplifiedthrough electronic chips located inside a computer. To addressthese failures, much research has been performed to developthermal management solutions for microelectronic devices.These solutions have generally been geared towards Si-basedmicroelectronics and have achieved cooling capabilities <strong>of</strong> 100W/cm 2 or greater. While such power densities are not expected inorganic semiconductors, these devices have unique thermal managementchallenges arising from their inherent low thermal conductivity(results in high thermal resistance), the use <strong>of</strong> thermallyresistive substrates for flexible electronics, and the need to havetransparent materials for photon transfer. Thus, new concepts forboth active and passive thermal management <strong>of</strong> organic semiconductordevices (OSD) must be explored.In this work, I will primarily concentrate on developing newschemes for the removal <strong>of</strong> thermal energy through both activeand passive mechanisms by “thermally connecting” the OSD tohigh thermal conductivity substrates. The thermal connection willbe based on carbon nanotubes (CNTs) which will act as a thermalinterface material (TIM) with superior properties to conventionalTIMs. These CNTs possess a very high thermal conductivity(900-10,000w/mk). I will investigate the use <strong>of</strong> multilayercatalysts to produce highly aligned CNTs on metal substrates andthe creation <strong>of</strong> actively cooled PMMA and Si (gold coated) substratesusing various bonding techniques. There is a severe lack<strong>of</strong> attention on the thermal characterization and heat dissipationin OSD. Much <strong>of</strong> what I do here will be new and provide muchneeded contributions to the challenges <strong>of</strong> thermal management inOSDs. In addition, with overheating <strong>of</strong> chips stalls the advancement<strong>of</strong> better electronic devices.The multilayer catalysts deposition onto metal substrateshas proven successful in producing some CNT growth (Figure1). Some parameters that contribute to this growth are the type<strong>of</strong> catalyst deposited onto the metal, the maximum temperatureduring the procedure, and the length that the sample is exposed tothe gases. By changing these parameters I am hoping to producea recipe that will generate better quality CNT growth with fewerdefects. Also, success was achieved at bonding Si (gold coated)to Si and PMMA to PMMA. Using a furnace, Si bonding canbe accomplished at 460 degrees Celsius for 5 minutes and is usedto for creating micr<strong>of</strong>luidic channels for active cooling. Concerningpolymers, a hydraulic press successfully bonded PMMAwith a carbon nan<strong>of</strong>iber interlayer at 250 degrees Fahrenheitwhile maintaining 400lbs <strong>of</strong> force for 5 minutes (Figure 2). Thislaminated structure was used to create a flexible heat spreaderin polymer substrates for improve heat dissipation. Future workwill involve finding a feasible bonding method for PET which ismore commonly used for flexible organic semiconductors and tocontinue to produce CNT growth onto metal substrates with theleast amount <strong>of</strong> defects.Figure 1. Growth <strong>of</strong> carbon nanotubes on a copper substrate (left) and ascanning electron microscope image showing the details <strong>of</strong> the growth (right).Figure 2. Growth <strong>of</strong> carbon nan<strong>of</strong>ibers (left) which werelaminated between sheets <strong>of</strong> PMMA to create a flexible heatspreader (right) integrated into a polymer substrate.ACKNOWLEDGEMENTSResearch support is gratefully acknowledged from the NationalScience Foundation Center on Materials and Devices forInformation Technology Research (CMDITR), DMR-0120967.CMDITR Review <strong>of</strong> Undergraduate Research Vol. 2 No. 1 Summer <strong>2005</strong> 83
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Synthesis of Nonlinear Optical-Acti
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