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    Open Access
    Input Visualization: Collecting and Modifying Data with Visual Representations
    (ACM, 2024-05-11) Bressa, Nathalie; Louis, Jordan; Willett, Wesley; Huron, Samuel
    We examine input visualizations, visual representations that are designed to collect (and represent) new data rather than encode preexisting datasets. Information visualization is commonly used to reveal insights and stories within existing data. As a result, most contemporary visualization approaches assume existing datasets as the starting point for design, through which that data is mapped to visual encodings. Meanwhile, the implications of visualizations as inputs and as data sources have received little attention—despite the existence of visual and physical examples stretching back centuries. In this paper, we present a design space of 50 input visualizations analyzing their visual representation, data, artifact, context, and input. Based on this, we identify input modalities, purposes of input visualizations, and a set of design considerations. Finally, we discuss the relationship between input visualization and traditional visualization design and suggest opportunities for future research to better understand these visual representations and their potential.
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    Open Access
    A vinylogous Norrish reaction as a strategy for light-mediated ring expansion
    (Royal Society of Chemistry, 2022-02-03) Evgueni Gorobets; James W. Papatzimas; Jorge Dourado; Goonay Yousefalizadeh; JinGyu Lee; Duncan K. Brownsey; Kevin Stamplecoskie; Rebecca Davis; Darren J. Derksen
    The reactions of bicyclic divinyl ketones display wavelength-dependent changes in product formation. UV irradiation results in the formation of competitive and tricyclic unsaturated ketones that subsequently undergo ring expansion and reaction with a range of nucleophiles. DFT calculations and transient absorption experiments were completed that are consistent with a vinylogous Type II Norrish pathway.
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    Open Access
    Generation of Benzyne Species from Diphenylphosphoryl Derivatives: Simultaneous Exchange of Three Functional Groups
    (European Chemical Societies Publishing, 2016-05-16) Evgueni Gorobets; Masood Parvez; Darren J. Derksen; Brian A. Keay
    Interaction of (2‐diphenylphosphoryl‐3‐iodo‐4‐methoxy‐phenyl) methanol with NaH in DMF at ambient temperature results in the generation of benzyne intermediates that can be trapped by furan or DMF. Trapping with DMF forms 3‐(dimethylaminomethyl)‐2‐hydroxy‐6‐methoxybenzaldehyde demonstrating the simultaneous exchange of three functionalities in a single step. The presence of the alkoxy substituent adjacent to iodine is critical for high regioselectivity addition of DMF. The corresponding bromide or triflate can be used in place of the iodide with equal efficiency. This methodology was used to synthesize the reported structure of gigasol and leading to a structural reassignment of this biscoumarin natural product.
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    Open Access
    Regioselective Synthesis of C3-Hydroxyarylated Pyrazoles
    (American Chemical Society, 2021-12-14) Leonie O’Sullivan; Ketul V. Patel; Ben C. Rowley; Duncan K. Brownsey; Evgueni Gorobets; Benjamin S. Gelfand; Jeffrey F. Van Humbeck; Darren J. Derksen
    Pyrazoles are ubiquitous structures in medicinal chemistry. We report the first regioselective route to C3-hydroxyarylated pyrazoles obtained through reaction of pyrazole N-oxides with arynes using mild conditions. Importantly, this method does not require the C4 and C5 positions of the pyrazole to be functionalized to observe regioselectivity. Using this method, we completed the synthesis of a recently reported JAK 1/2 inhibitor. Our synthesis produces the desired product in 4 steps from commercially available starting materials.
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