Student Project Abstracts 2005 - Pluto - University of Washington

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SYNTHESIS AND CHARACTERIZATION OF EXTENDED SQUARAINE COMPOUNDSScheme 4. Synthesis of 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 of 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 of 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 ofTechnology 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 of Undergraduate Research Vol. 2 No. 1 Summer 2005
Enhanced Heat Dissipation Substrates for Organic Semiconductor DevicesAaron MontgomeryUniversity of VirginiaDr. Samuel GrahamGeorgia Institute of TechnologyAshante Allen, Erik Sunden and Adam Christensen`Many electronic devices are susceptible to overheatingwhich can result in failures of 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 of 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 of thermallyresistive substrates for flexible electronics, and the need to havetransparent materials for photon transfer. Thus, new concepts forboth active and passive thermal management of organic semiconductordevices (OSD) must be explored.In this work, I will primarily concentrate on developing newschemes for the removal of 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 of multilayercatalysts to produce highly aligned CNTs on metal substrates andthe creation of actively cooled PMMA and Si (gold coated) substratesusing various bonding techniques. There is a severe lackof attention on the thermal characterization and heat dissipationin OSD. Much of what I do here will be new and provide muchneeded contributions to the challenges of thermal management inOSDs. In addition, with overheating of chips stalls the advancementof 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 typeof 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 microfluidic channels for active cooling. Concerningpolymers, a hydraulic press successfully bonded PMMAwith a carbon nanofiber interlayer at 250 degrees Fahrenheitwhile maintaining 400lbs of 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 of defects.Figure 1. Growth of carbon nanotubes on a copper substrate (left) and ascanning electron microscope image showing the details of the growth (right).Figure 2. Growth of carbon nanofibers (left) which werelaminated between sheets of 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 of Undergraduate Research Vol. 2 No. 1 Summer 2005 83
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TABLE OF CONTENTSSynthesis of Dendr
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SYNTHESIS OF DENDRIMER BUILDING BLO
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throughout the work period. Five su
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BARIUM TITANATE DOPED SOL-GEL FOR E
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BARIUM TITANATE DOPED SOL-GEL FOR E
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SYNTHESIS OF NORBORNENE MONOMER OF
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using different reaction conditions
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Synthesis of Nonlinear Optical-Acti
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quality of the XRD structures wasca
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Behavioral Properties of Colloidal
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Page 38 and 39: Fabry-Perot modulators with electro
Page 42 and 43: QUANTIZED HAMILTON DYNAMICS APPLIED
Page 46 and 47: INVESTIGATING NEW CLADDING AND CORE
Page 48 and 49: Dr. Robert NorwoodChris DeRoseAmir
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Page 54 and 55: OPTIMIZING HYBRID WAVEGUIDESpropaga
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Page 58 and 59: SYNTHESIS AND ANALYSIS OF THIOL-STA
Page 62 and 63: QUINOXALINE-CONTAINING POLYFLUORENE
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Page 68 and 69: SYNTHESIS OF DENDRON-FUNCTIONALIZED
Page 72 and 73: BUILDING AN OPTICAL OXIMETER TO MEA
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Page 104 and 105: CHARACTERIZATION OF THE MOLECULAR P
Page 108 and 109: OPTIMIZATION OF SEMICONDUCTOR NANOP
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Page 112 and 113: CHARACTERIZATION OF THE PHOTODECOMP
Page 116 and 117: ELECTROLUMINESCENT PROPERTIES OF OR
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Page 128 and 129: THE DESIGN OF A FLUID DELIVERY SYST
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Student Project Abstracts 2005 - Pluto - University of Washington

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