Thompson, Alison: Recent submissions

Now showing items 1-20 of 57

  • BODIPYs with Chalcogenophenes at Boron: Synthesis and Properties. Postprint 

    BODIPYs with Chalcogenophenes at Boron: Synthesis and Properties Jacob W. Campbell, Matthew T. Tung, Katherine N. Robertson, Andrew A. Beharry, and Alison Thompson The Journal of Organic Chemistry Article ASAP DOI: 10.1021/acs.joc.3c00708
    Reported herein are the synthesis and characterization of BODIPYs bearing heterocycles at boron. To synthesize this series, various chalcogenophenes (furan, thiophene, selenophene, and tellurophene) were lithiated and then ...

  • Bridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffolds 

    Grover, N., Locke, G. M., Flanagan, K. J., Beh, M. H., Thompson, A., & Senge, M. O. (2020). Bridging and Conformational Control of Porphyrin Units through Non‐Traditional Rigid Scaffolds. Chemistry–A European Journal.
    Connecting two porphyrin units in a rigid linear fashion, without any undesired electron delocalization or communication between the chromophores, remains a synthetic challenge. Herein, a broad library of functionally ...

  • Synthesis, properties and reactivity of BCl2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold 

    Diaz-Rodriguez, R. M., Burke, L., Robertson, K. N., & Thompson, A. (2020). Synthesis, properties and reactivity of BCl 2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold. Organic & Biomolecular Chemistry, 18(11), 2139-2147.
    The synthesis and characterisation of the BCl2-chelated complexes of both archetypal aza-dipyrrin sub- types are presented. A stepwise halogen exchange, leading to a mixed-halide Cl–B–F intermediate, is implicated in the ...

  • Bridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffolds 

    Grover, Nitika; Locke, Gemma M.; Flanagan, Keith J.; Beh, Michael H. R.;Beh, Thompson, Alison; and Senge, Mathias O. (2019). Bridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffolds. Chemistry: A European Journal, 26,11. https://doi.org/10.1002/chem.201904199
    Connecting two porphyrin units in a rigid linear fashion, without any undesired electron delocalization or communication between the chromophores, remains a synthetic challenge. Herein, a broad library of functionally ...

  • Bis[Pyrrolyl Ru(II)] Triads: a New Class of Photosensitizers for Metal-Organic Photodynamic Therapy 

    Smithen, D. A., Monro, S., Pinto, M., Roque III, J. A., Diaz-Rodriguez, R. M., Yin, H., ... & Yin, H. (2020). Bis [Pyrrolyl Ru (II)] Triads: a New Class of Photosensitizers for Metal-Organic Photodynamic Therapy. doi.org/10.26434/chemrxiv.12824216.v1
    A new family of ten dinuclear Ru(II) complexes based on the bis[pyrrolyl Ru(II)] triad scaffold, where two Ru(bpy)2 centers are separated by a variety of organic linkers, was prepared to evaluate the influence of the ...

  • Synthesis of sulfenyl dipyrroles via reaction of a-free pyrroles with thionyl chloride 

    Beh, Michael H. R.; Smith, Craig D.; Robertson, Katherine N.; and Thompson, Alison. (2020). Synthesis of sulfenyl dipyrroles via reaction of a-free pyrroles with thionyl chloride. Canadian Journal of Chemistry,

  • Facile Deprotection of F-BODIPYs using Methylboronic Acid 

    4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) are deprotected through removal of the –BF2 moiety upon treatment with methylboronic acid. The tolerance of various substitution patterns about the dipyrrinato core ...

  • Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles 

    Kim, Min Joon; Gaube, Sophie M.; Beh, Michael H. R.; Smith, Craig D.; Thompson, Alison. (2019). RSC Advances.
    2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesized using a Knorr-type approach ...

  • The Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes 

    Hilborn, James W., Moya-Barrios, Reinaldo, Thompson, Alison. (2019). The Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes. ACS Publication (pre-publication).
    The synthesis of naphthylarylethanes via the photodecarboxylation of naphthylmethyl arylacetate esters is reported where the aryl group is able to stabilize a charge transfer reaction. The reaction proceeds via intramolecular ...

  • Classifying donor strengths of dipyrrinato/aza-dipyrrinato ligands 

    Diaz-Rodriguez, Roberto M., Robertson, Katherine N., and Thompson, Alison. (2019). Classifying donor strengths of dipyrrinato/aza-dipyrrinato ligands. Dalton Transactions.
    A parameter is reported by which to use 13C NMR chemical shifts to measure and predict the donor capabilities of N^N dipyrrinato and aza-dipyrrinato ligands chelating in L^X fashion. The results enable the rationalisation ...

  • Step-wise synthetic approach is necessary to access g-conjugates of folate: folate-conjugated prodigiosenes 

    Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the ...

  • Synthesis of Prodigiosene-Estrogen Conjugates: optimization of protecting group strategies and anticancer properties 

    Marchal, E., Uddin, M. I., Hawco, C. L., & Thompson, A. (2015). Synthesis of prodigiosene–estrogen conjugates: optimization of protecting group strategies and anticancer properties. Canadian Journal of Chemistry, 93(5), 526-535. https://doi.org/10.1139/cjc-2014-0516
    The tripyrrolic prodigiosene skeleton was conjugated to several estrogen ligands. The conjugation was achieved via an ester linker that proved to be unusually sensitive to hydrolysis during synthesis. This work describes ...

  • Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles 

    Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles. Beh, M.H.R.; Figliola, C.; Lund, K-l. A.R.; Kajetanowicz, A.K.; Johnsen, A.E.; Aronitz, E.M.; Thompson, A. Can. J. Chem. 2018, 96, 779-784, special issue to honour Dalhousie’s 200th anniversary (NSERC). https://doi.org/10.1139/cjc-2017-0662
    The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through the adoption of two mechanistic pathways. The key ...

  • Synthesis of symmetric meso-H dipyrrin hydrobromides from 2-formyl pyrroles 

    Lund, K. L. A., & Thompson, A. (2014). Synthesis of Symmetric meso-H-Dipyrrin Hydrobromides from 2-Formylpyrroles. Synlett, 25(08), 1142-1144. DOI: 10.1055/s-0033-1341066
    The reaction of 2-formyl pyrroles in acidic methanol gives the corresponding symmetric, meso-H 4,6-dipyrrin hydrobromides. This convenient strategy involves initial deformylation under the acidic conditions, followed by ...

  • The Use of Tin (IV) Chloride to Selectively Cleave Benzyl Esters over Benzyl Ethers and Benzyl Amines 

    Baker, A. E., Marchal, E., Lund, K. L. A., & Thompson, A. (2014). The use of tin (IV) chloride to selectively cleave benzyl esters over benzyl ethers and benzyl amines. Canadian Journal of Chemistry, 92(12), 1175-1185. https://doi.org/10.1139/cjc-2014-0364
    Benzyl esters are cleaved upon reaction with SnCl4, resulting in isolation of the corresponding carboxylic acid. Importantly, benzyl ethers, amines and amides do not undergo debenzylation under these conditions, nor do a ...

  • Antimicrobial Activity of Non-natural Prodigiosenes 

    Marchal, E., Uddin, M. I., Smithen, D. A., Hawco, C. L. A., Lanteigne, M., Overy, D. P., ... & Thompson, A. (2013). Antimicrobial activity of non-natural prodigiosenes. Rsc Advances, 3(45), 22967-22971. DOI: 10.1039/c3ra45479g
    Tripyrrolic prodigiosenes, derivatives of the natural product prodigiosin, have been produced via multi-step synthesis beginning with 2-formyl pyrroles bearing various functionalities at the 4-position. Two tin complexes ...

  • Activation and Deprotection of F-BODIPYs using Boron Trihalides 

    Lundrigan, Travis, Cameron, T. Stanley, Thompson, Alison. (2014). Activation and deprotection of F-BODIPYs using boron trihalides. Chemical Communications, 50(53), 7028-7031. DOI: 10.1039/C4CC02706J
    The activation of F-BODIPYs with boron trihalides, followed by treatment with a nuclephile, effects facile substitution at boron; using water as the nucleophile promotes deprotective removal of the–BF2 moiety and thereby ...

  • Synthesis and Characterization of Pyrrolyldipyrrin F-BODIPYs 

    Greening, S. M., Robertson, K. N., & Thompson, A. (2018). Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs. Photochemical & Photobiological Sciences, 17(1), 89-98. DOIO: 10.1039/C7PP00341B
    A series of synthetic analogs of the tripyrrolic natural product prodigiosin were complexed with boron trifluoride to generate the corresponding F-BODIPYs. The maximum wavelengths of absorption and emission of the ...

  • Photo-induced Anticancer Activity and Singlet Oxygen Production of Prodigiosenes 

    Savoie, H., Figliola, C., Marchal, E., Crabbe, B. W., Hallett-Tapley, G. L., Boyle, R. W., & Thompson, A. (2018). Photo-induced anticancer activity and singlet oxygen production of prodigiosenes. Photochemical & Photobiological Sciences, 17(5), 599-606. DOI: 10.1039/C8PP00060
    The photo-induced cytotoxicity of prodigiosenes is reported. One prodigiosene represents a synthetic analogue of the natural product prodigiosin, and two are conjugated to molecules that target the estrogen receptor (ER). ...

  • Synthesis and Reactivity of Aza-Dipyrrin Alkali Metal Salts 

    Synthesis and Reactivity of Aza-Dipyrrin Alkali Metal Salts. Diaz-Rodriguez, R.M.; Robertson, K.N.; Thompson, A. Chem. Commun. 2018, accepted, CC-COM-09-2018-007101.R1 (NSERC) DOI: 10.1039/C8CC07101B
    We report the lithium, sodium and potassium salts of aza-dipyrrins and detail their use as anionic aza-dipyrrinato ligand sources in complexation. Of the three types of alkali salts studied, those of lithium are found to ...