CMDITR Review of Undergraduate Research - Pluto - University of ...

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Suzuki Coupling (4) The phenyl-pyridine structure was synthesized by coupling 3 with 3- formalphenylboronic acid via the Suzuki coupling giving compound 4 in 45% yield. The reaction was carried out in dioxane, oxygen and light free. The solvents, THF and Aqueous K 2 CO 3 were sparged for an hour and the reaction apparatus was covered in aluminum foil. To a solution of 3 (1g, .0054mol), 3- formalphenylboronic acid (.81g, 0.0054mol) and Pd(0)(PPh3)4 catalyst (0.03% mol wt), aqueous K 2 CO 3 (1.2g, 0.0087mol) was added dropwise at 100ºC. The reaction was stirred at temperature for 48 hours under nitrogen. The dioxane was removed under reduced pressure and the product was extracted with methylene chloride. The methylene chloride layer was dried over sodium sulfate before being removed under reduced vacuum yielding crude product. The crude product was purified on a silica gel column ran with 10% ethyl acetate in methylene chloride. Product was the second band resulting in white solid. Mass Spec; fragments at 212.0g/mol, 198.0g/mol, and 184.0g/mol. Horner Emmons (5) The aldehyde of 4 was reacted with the donor phosphate giving compound 5 in 25% yield. To a solution of 4 (0.7g, 0.0035mol) and N-dibutylaniline phosphinate (2.67g, 0.0078mol) in dry THF, potassium butoxide (14mL, 0.014mol) was added dropwise at 0ºC resulting in an immediate color change to dark green and highly florescent. The reaction stirred at room temperature for 18 hours. The THF was removed under reduced pressure and the resulting solid was taken in methylene chloride and given subsequent water washes. The methylene chloride layer was dried over sodium sulfate and removed under reduced pressure resulting in crude product. The crude product was purified on a silica gel column ran with a liquid phase of 20% ethyl acetate in methylene chloride. The product was the first red band. The red color was due to the ligand complexing with the silica. The poor yield was due to the decomposition of starting material by potassium butoxide, future reactions will be ran with milder conditions. Mass Spec, dominate peaks at: 614.4g/mol, 399.2g/mol, and 234.2g/mol. Iridium Complexing 56 CMDITR Review of Undergraduate Research Vol. 1 No. 1 Summer 2004
Results The ligand was synthesized following the scheme shown. The yield of steps 1 and 2 were poor resulting in 20% product from 2-bromo-4- methylpyridine to 2-bromo-4-formalpyridine. The poor yield is probably due to the difficulty in removing DMF from the first step, which may cause product decomposition if allowed to remain for an extended time. If the ligand proves useful steps will be taken to optimize these steps. The next phase will be attaching the ligand to an IrCl 3 complex. Once this is accomplished, the hybrid chromophore will be submitted for device testing to measure the chromophores ability as an EO material. Future ligand projects will include crosslinking functionalization with the ultimate goal of device applications without doping the chromophore in a host polymer which is be the highest loading density possible. References 1. Bouder, T. and J. Zyss,. 2003. J. Am. Chem. Soc. 125:12284-12299 2. Dalton, L. 1999. J. Mater. Chem. 9:1905- 1920. 3. Dalton, Larry. 2002. Nonlinear Optical Polymeric Materials: from Chromophore Design to Commercial Applications. Advances in Polymer Science, Springer- Verlag Berlin Heidelberg. 158. 4. Vance, F. and J. Hupp, 1999. J. Am. Chem. Soc. 121:4047-4053 5. Viau, Lydie. 2003. Synthesis. 4:577-583. CMDITR Review of Undergraduate Research Vol. 1 No. 1 Summer 2004 57
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CMDITR Review of Undergraduate Rese
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Welcome to the premier issue of the
Page 5 and 6: Extended Abstracts Table of Content
Page 7 and 8: wt % THV 220A). The glass tube was
Page 9 and 10: Fiber cladding preparation In order
Page 11 and 12: Acknowledgements Brian Ratliff, Gra
Page 13 and 14: Figure 2. Synthesis of the dendrime
Page 15 and 16: Toward the Synthesis of a Magnetic
Page 17 and 18: Results and Discussion Synthesis of
Page 19 and 20: years, (13) decomposes into a yello
Page 21 and 22: References 1. (a) MacDiarmid, A.G.
Page 23 and 24: suggests that any effects of these
Page 25 and 26: Electrospinning of Piezoelectric Ma
Page 27 and 28: varies and is close to the critical
Page 29 and 30: Synthesis of Azaindoly-phenanthroli
Page 31 and 32: Experimental Physical Measurements.
Page 33 and 34: [60] fullerene enable close packing
Page 35 and 36: Crystallization. We attempted to cr
Page 37 and 38: number of solvents including aceton
Page 39 and 40: References 1. Dalton, L.R. 2003. No
Page 41 and 42: though the beads were moving becaus
Page 43 and 44: Feasibility of Hydroxy-Chalcone Lin
Page 45 and 46: absorbance is proportional to conce
Page 47 and 48: Results Linear Dichroism Metripol c
Page 49 and 50: Pararosaniline Xylene Cyanole FF Cr
Page 51 and 52: the source of the light emitted by
Page 53 and 54: Figure 6. UV and PL spectra of the
Page 55: Method The hybrid chromophore will
Page 59 and 60: Following the cooling down, the pro
Page 61 and 62: Two-Photon Induced Free Radical Pol
Page 63: Future Work When the results of the
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