- NSERC Postdoctoral Research Fellow (2010-2012), Columbia University (J. L. Leighton)
- Ph.D. (2009), University of Alberta (R. R. Tykwinski)
- B.S. (2004), University of Alberta
Research in the Chalifoux laboratory is focused on the development of new methodologies for organic synthesis that provide more efficient access to complex intermediates. We aim to utilize the reactivity of highly functionalized yet easily prepared ynone precursors to rapidly provide a diverse array of products through intermolecular domino reactions, intramolecular tandem reactions and multicomponent reactions. These new methodologies are applicable not only to the synthesis of complex natural products and intermediates, but also to the development of materials of both practical and theoretical interest.
Our group seeks to apply the strengths of complex small molecule synthesis to the challenges of organic materials chemistry, in an effort to develop new organic and organometallic materials with a host of desirable properties and varying uses. One particularly appealing application of this approach is toward the rational design of molecular cages for the specific binding of target substrates for use as biosensors, molecular switches and nanoreactors.
Polyconjugated organic and organometallic materials are desirable in the areas of nonlinear optics (NLO), thin-film transistors (TFTs), organic light-emitting diodes (OLEDs), synthetic receptors, and molecular switches because the properties of organic materials are easily tuned through synthesis. Another advantage to using these soft materials is that they are easy to process and require less expensive device fabrication techniques. We have a program designated to the synthesis and study of new polyconjugated materials and utilizing these advanced materials in the various applications described above.
- Chalifoux, W. A.; Reznik, S. K.; Leighton, J. L. Direct and Highly Regioselective and Enantioselective Allylation of β-Diketones. Nature 2012, 487, 86-89.
- Lucotti, A.; Tommasini, M.; Fazzi, D.; Del Zoppo, M.; Chalifoux, W. A.; Tykwinski, R. R.; Zerbi, G. Absolute Raman Intensity Measurements and Determination of the Vibrational Second Hyperpolarizability of Adamantyl Endcapped Polyynes. J. Raman Spectrosc. 2012, in press (DOI: 10.1002/jrs.3166)
- Lucotti, A.; Tommasini, M.; Chalifoux, W. A.; Fazzi, D.; Zerbi, G.; Tykwinski, R. R. Bent Polyynes: Ring Geometry Studied by Raman and IR Spectroscopies. J. Raman Spectrosc. 2012, 43, 95-101.
- Chalifoux, W. A.; Ferguson, M. J.; McDonald, R.; Melin, F.; Echegoyen, L.; Tykwinski R. R. Adamantyl Endcapped Polyynes. J. Phys. Org. Chem. 2011, 25, 69-76.
- Yildizhan, M. M.; Fazzi, D.; Milani, A.; Brambilla, L.; Del Zoppo, M.; Chalifoux, W. A.; Tykwinski, R. R.; Zerbi, G. Photogenerated Cumulenic Structure of Adamantyl Endcapped Linear Carbon Chains: An Experimental and Computational Investigation based on Infrared Spectroscopy. J. Chem. Phys. 2011, 134, 124512:1-8.
- Chalifoux, W. A.; Tykwinski, R. R. Synthesis of Polyynes to Model the sp-Carbon Allotrope Carbyne. Nature Chem. 2010, 2, 967-971.
- Tykwinski, R. R.; Chalifoux, W. A.; Eisler, S.; Lucotti, A; Tommasini, M.; Fazzi, D.; Del Zoppo, M.; Zerbi, G. Toward Carbyne: Synthesis and Stability of Really Long Polyynes. Pure Appl. Chem. 2010, 82, 891-904.
- Chalifoux, W. A.; McDonald, R.; Ferguson, M. J.; Tykwinski, R. R. t-Butyl Endcapped Polyynes: Crystallographic Evidence of Reduced Bond Length Alternation. Angew. Chem. Int. Ed. 2009, 48, 7915-7919.
- Lucotti, A.; Tommasini, M.; Fazzi, D.; Del Zoppo, M.; Chalifoux, W. A.; Ferguson, M. J.; Zerbi, G.; Tykwinski, R. R. Evidence for Solution-state Nonlinearity of sp-Carbon Chains Based on IR and Raman Spectroscopy. J. Am. Chem. Soc. 2009, 131, 4239-4244.
- Bichler, P.; Chalifoux, W. A.; Eisler, S.; Shi Shun, A. L. K.; Chernick, E. T.; Tykwinski, R. R. Mechanistic Aspects of Alkyne Migration in Alkylidene Carbenoid Rearrangements. Org. Lett. 2009, 11, 519-522.
- Chalifoux, W. A.; Tykwinski, R. R. Synthesis of Extended Polyynes: Toward Carbyne. C. R. Chim. 2009, 12, 341-358.
- Chalifoux, W. A.; Tykwinski, R. R. Tris(biphenyl-4-yl)silyl-Endcapped Polyynes. Eur. J. Org. Chem. 2007, 1001-1006.
- Chalifoux, W. A.; Tykwinski, R. R. Polyyne Synthesis Using Carbene/Carbenoid Rearrangements. Chem. Rec. 2006, 6, 169-182.