Chalifoux Research Group

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1. Walley, M. S.; Horton, J. A.; Reilly, D.; Chien, L.; Catalano, V. J.; Chalifoux, W. A. "Enantioselective BINOL-Aluminum-Chloride-Catalyzed Diels-Alder Reaction of Ynones and Activated Dienes," manuscript in preparation.

2. Wang, Y.; Li, M.; Yao, L.; Chalifoux, W. A.; Yang, W. "Controlled Synthesis of Isomeric λ5-Phosphaphenanthrene from Alkynyl-phosphonium Salts," under revision.

3. Bates, M.; Malone, R. J.; Yang, C.; Chalifoux, W. A.; Lunt, R. R. "Graphene Nanoribbon Photovoltaics," under revision.

4. Bam, R.; Yang, W.; Longhi, G.; Abbate, S.; Lucotti, A.; Tommasini, M.; Franzini, R.; Villani, C.; Catalano, V. J.; Olmstead, M. M.; Chalifoux, W. A. "Chiral Teropyrene: Synthesis, Structure, and Spectroscopic Properties," submitted.

5. George, S. P.; Spengler, J.; Malone, R. J.; Krzoska, J.; Würthner, F.; Chalifoux, W. A. “Dissymmetrical Chiral Peropyrenes: Synthesis via Iridium Catalyzed C-H Activation/Alkyne Benzannulation and Study of Their Properties,” J. Org. Chem. 2024, 89, 5159 (link).

6. Anderson, H. V.; Gois, N. D.; Chalifoux, W. A. "New Advances in Chiral Nanographene Chemistry," Org. Chem. Front. 2023, 10, 4167 (link).

7. Malone, R. J.; Spengler, J.; Carmichael, R. A.; Ngo, K.; Würthner, F.; Chalifoux, W. A. "Synthesis and Properties of Achiral and Chiral Dipyrenoheteroles and Related Compounds," Org. Lett. 2023, 1, 226 (link).

8. Schroeder, Z. W.; McDonald, R.; Ferguson, M. J.; Chalifoux, W. A.; Tykwinski, R. R.; Lehnherr, D. "Pentacenones as Divergent Intermediates to Unsymmetrically Substituted Pentacenes: Synthesis and Crystallographic Analysis," J. Org. Chem., 2022, 87, 16236 (link).

9. Islam, S. M.; Malone, R. J.; Yang, W.; George, S. P.; Chalifoux, W. A.; Barile, C. J. "Nanographene Cathode Materials for Nonaqueous Zn-ion Batteries," J. Electrochem. Soc., 2022, 169, 110517 (link).

10. Chalifoux, W. A.; Sitaula, P.; Malone, R. J.; Longhi, G.; Abbate, S.; Gualtieri, E.; Lucotti, A.; Tommasini, M.; Franzini, R.; Villani, C.; Catalano, V. J. “π-Extended Helical Nanographenes: Synthesis and Photophysical Properties of Naphtho[1,2-a]pyrenes,” Eur. J. Org. Chem. 2022, e202101466. (link).

11. • VIP paper​

    • Highlight in ChemistryViews

12. Sitaula, P.; Malone, R. J.; Longhi, G.; Abbate, S.; Gualtieri, E.; Lucotti, A.; Tommasini, M.; Franzini, R.; Villani, C.; Catalano, V. J.; Chalifoux, W. A. “π-Extended Helical Nanographenes: Synthesis and Photophysical Properties of Naphtho[1,2-a]pyrenes,” ChemRxiv. Preprint. https://doi.org/10.26434/chemrxiv.12931703.v1.

13. Magiera, K. M.; Aryal, V.; Chalifoux, W. A. "Alkyne benzannulations in the preparation of contorted nanographenes," Org. Biomol. Chem. 2020, 18, 2372. (link)

14. Bam, R.; Yang, W.; Longhi, G.; Abbate, S.; Lucotti, A.; Tommasini, M.; Franzini, R.; Villani, C.; Catalano, V. J.; Olmstead, M. M.; Chalifoux, W. A. “Four-fold Alkyne Benzannulation: Synthesis, Properties, and Structure of Pyreno[a]pyrene-Based Helicene Hybrids,” Org. Lett. 2019, 21, 8652. (link)

15. De Hoe, C.; Dean, R. T.; Hacker, A. S.; Dutta, S. H.; Dominguez, O.; Parsons, L. W. T.; Sommerville, P. J. W.; Vandivier, K. P.; Chalifoux, W. A.; Frantz, D. K. Synthesis and Structure of a Strained, Cyclic meta-Quaterphenylene Acetylene,” Eur. J. Org. Chem. 2019, 4522. (link)

16. Hamal, K. B.; Sitaula, P.; Chalifoux, W. A. “Synthesis of Dihydroisobenzofuran Carboxaldehyde Derivatives by a Silver-catalyzed Sequential Protodesilylation/Cyclization/Oxidation Reaction,” Eur. J. Org. Chem. 2019, 1225. (link)

17. Senese, A. D.; Chalifoux, W. A. “Nanographene and Graphene Nanoribbon Synthesis via Alkyne Benzannulations,” Molecules 2019, 24, 118. (link)

18. Yang, W.; Monteiro, J. H. S. K.; de Bettencourt-Dias, A.; Catalano, V. J.; Chalifoux, W. A. “Synthesis, Structure, Photophysical Properties, and Photostability of Benzodipyrenes,” Chem. Eur. J. 2019, 25, 1441. (link)

19. Yang, W.; Bam, R.; Catalano, V. J.; Chalifoux, W. A. “Highly Regioselective Domino Benzannulation Reaction of Buta‐1,3‐diynes to Construct Irregular Nanographenes,” Angew. Chem. Int. Ed. 2018, 57, 14773. (link)

    • Selected for the inside cover.

    • Highlighted in Synfacts 2018, 14(12), 1249.

20. Bam, R.; Chalifoux, W. A. “One-pot Domino Friedel-Crafts Acylation/Annulation between Alkynes and 2-Methoxybenzoyl Chlorides: Synthesis of 2,3-Disubstituted Chromen-4-one Derivatives,” J. Org. Chem. 2018, 83, 9929. (link)

21. Yang, W; Kazemi, R. R.; Karunathilake, N.; Catalano, V. J.; Alpuche-Aviles, M. A.; Chalifoux, W. A. “Expanding the scope of peropyrenes and teropyrenes through a facile InCl3-catalyzed multifold alkyne benzannulation,” Org. Chem. Front. 2018, 5, 2288. (link)

    • Selected for the front cover.

22. Hamal, K. B.; Chalifoux, W. A. “One-Pot Synthesis of α-Carbonyl Bicyclic Furans via a Sequential Diels-Alder/5-Exo-Dig Cyclization/Oxidation Reaction,” J. Org. Chem. 2017, 82, 12920. (link)

23. Yang, W.; Longhi, G.; Abbate, S.; Lucotti, A.; Tommasini, M.; Villani, C.; Catalano, V. J.; Lykhin, A. O.; Varganov, S. A.; Chalifoux, W. A. “Chiral Peropyrene: Synthesis, Structure, and Properties,” J. Am. Chem. Soc. 2017, 139, 13102. (link)

    • Highlighted in Synfacts 2017, 13(11), 1150.

24. Carmichael, R. A.; Sophanpanichkul, P.; Chalifoux, W. A. “ß-Silyl-Assisted Tandem Diels-Alder/Nazarov Reaction of 1-Aryl-3-(Trimethylsilyl) Ynones,” Org. Lett. 2017, 19, 2592. (link)

25. Chalifoux, W. A. “The Synthesis of Non-planar, Helically Coiled Graphene Nanoribbons,” Angew. Chem. Int. Ed. 2017, 56, 8048. (link)

    • Invited Highlight paper (see Morin's original paper here).

26. Yang, W.; Chalifoux, W. A. “Rapid π-Extension of Aromatics via Alkyne Benzannulations,” Synlett 2017, 28, 625. (link)

    • Invited SYNPACTS paper.

27. Carmichael, R. A.; Chalifoux, W. A. “One-pot Synthesis of [6-5-6] Tricyclic Products via a Double Diels-Alder/Nazarov Tandem Reaction of Unsymmetrically Substituted Cross-conjugated Diynones,” Tetrahedron 2017, 73, 4084. (link)

    • Invited paper for a Symposium-in-Print titled “New Advances in Pericyclic Reactions.”

28. Prenzel, D; Kirschbaum, R. W.; Chalifoux, W. A.; McDonald, R; Ferguson, M. J.; Drewello, T.; Tykwinski, R. R. “Polymerization of acetylene: polyynes, but not carbyne,” Org. Chem. Front. 2017, 4, 668. (link)

29. Yang, W.; Monteiro, J. H. S. K.; de Bettencourt-Dias, A.; Chalifoux, W. A. "New Thiophene-Functionalized Pyrene, Peropyrene, and Teropyrene via a Two- or Four-fold Alkyne Annulation and Their Photophysical Properties," Can. J. Chem. 2017, 95, 341. (link)

    • Invited paper for a special issue in honor of Professor Reginald H. Mitchell.

30. Yang, W.; Lucotti, A.; Tommasini, M.; Chalifoux, W. A. "Bottom-Up Synthesis of Soluble and Narrow Graphene Nanoribbons Using Alkyne Benzannulations," J. Am. Chem. Soc. 2016, 138, 9137. (link)

    • Highlighted in Synfacts 2016, 12(09), 0912.

31. Yang, W.; Monteiro, J. H. S. K.; de Bettencourt-Dias, A.; Catalano, V. J.; Chalifoux, W. A. "Pyrenes, Peropyrenes, and Teropyrenes: Synthesis, Structures, and Photophysical Properties," Angew. Chem. Int. Ed. 2016, 55, 10427. (link)

32. Agarwal, N. R; Lucotti, A.; Tommasini, M.; Chalifoux, W. A.; Tykwinski, R. R. "Nonlinear Optical Properties of Polyynes: An Experimental Prediction For Carbyne," J. Phys. Chem. C 2016, 120, 11131. (link)

33. Chalifoux, W. A. “Profile: Early Excellence in Physical Organic Chemistry,” J. Phys. Org. Chem., 2016, 29, 686-687. (link)

34. Carmichael, R. A.; Chalifoux, W. A. "Multicomponent Double Diels-Alder/Nazarov Tandem Cyclization of Symmetric Cross-conjugated Diynones to Generate [6-5-6] Tricyclic Products," Chem. Eur. J. 2016, 22, 8781. (link)

35. Hamal, K. B.; Bam, R.; Chalifoux, W. A. "Synthesis of 2-Alkynyl-1,4-cyclohexadienes via a Diels–Alder Reaction of Conjugated 2,4-Diynones," Synlett 2016, 27, 2161. (link)

    • Highlighted in Synform.

36. Sproul, K. C.; Chalifoux, W. A. "Highly Regio- and Diastereoselective Formation of Tetrasubstituted (Z)-1,2-Dihaloalkenes from the Halogenation of Trimethylsilyl Alkynes with ICl," Org. Lett. 2015, 17, 3334. (link)

37. Agarwal, N. R.; Lucotti, A; Fazzi, D.; Tommasini, M.; Castiglioni, C.; Chalifoux, W. A.; Tykwinski, R. R. "Structure and chain polarization of long polyynes investigated with infrared and Raman spectroscopy," J. Raman. Spectrosc. 2013, 44, 1398. (link)

38. Chalifoux, W. A.; Reznik, S. K.; Leighton, J. L. "Direct and Highly Regioselective and Enantioselective Allylation of β-Diketones," Nature 2012, 487, 86. (link)

39. 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, 43, 1293. (link)

40. 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. (link)

41. 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. (link)

42. 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. (link)

43. Chalifoux, W. A.; Tykwinski, R. R. “Synthesis of polyynes to model the sp-carbon allotrope carbyne,” Nature Chem. 2010, 2, 967. (link)

    • Reviewed in Current Science 2011, 100 (4), 453 (link).

    • Reviewed in Nature Chemistry (doi:10.1038/nchem.884).

    • Reviewed in Chemical and Engineering News 2010, 88(38), 25 (link).

    • Reviewed in Nachrichten aus der Chemie 2010, 58, 1220 (doi:10.1002/nadc.201077722).

    • Commented on by Nobel Laureate Sir Harold W. Kroto in Chemistry World.

    • Commented on in Chemistry World.

44. 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. (link)

45. 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. (link)

    • This was regarded as a very important paper (VIP).

    • Highlighted in Angewandte Chemie International Edition (doi:10.1002/anie.200904145).

    • Highlighted in Nature Chemistry (doi:10.1038/nchem.398).

46. 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. (link)

47. 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. (link)

48. Chalifoux, W. A.; Tykwinski, R. R. “Synthesis of Extended Polyynes: Toward Carbyne,” C. R. Chim. 2009, 12, 341. (link)

49. Chalifoux, W. A.; Tykwinski, R. R. “Tris(biphenyl-4-yl)silyl-Endcapped Polyynes,” Eur. J. Org. Chem. 2007, 1001. (link)

50. Chalifoux, W. A.; Tykwinski, R. R. “Polyyne Synthesis Using Carbene/Carbenoid Rearrangements,” Chem. Rec. 2006, 6, 169. (link)

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