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Creators/Authors contains: "Demachkie, Isabella_S"

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  1. ; ; ; ; ; ; (, Angewandte Chemie International Edition)
    Abstract Herein we report the synthesis and characterization of four donor/acceptor‐fuseds‐indacenes via the late‐stage oxidation of a family of unsymmetrical benzofuran/benzothiophene‐s‐indacene regioisomers. A thorough study of their properties through experimental and computational analysis has revealed the effect of asymmetry on the molecular properties associated with antiaromaticity, as well as a strong correlation between antiaromaticity and intramolecular charge transfer (ICT). The strength of the charge transfer depends on the fusion orientation of the donor and acceptor motifs relative to thes‐indacene core. The two most antiaromatic oxidized isomers exhibit strong evidence of ICT with 30 and 40 nm solvatochromic shifts. 
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  2. ; ; ; ; ; ; (, European Journal of Organic Chemistry)
    Abstract Cyclophanes are a fundamentally interesting class of compounds that host a wide range of unique and emergent properties. However, synthesis of complex and/or functionalized cyclophanes can often suffer from harsh reaction conditions, long reaction times, and sometimes low yields using stepwise methods. We have previously reported an efficient, high‐yielding, metalloid‐directed self‐assembly method to prepare disulfide, thioether, and hydrocarbon cyclophanes and cages that feature mercaptomethyl‐arenes as starting materials. Herein, we report the synthesis of 21 new disulfide and thioether assemblies that expand this high yielding self‐assembly method to a wide breadth of macrocycles and cages with diverse structures. Remarkably, the high‐yielding, efficient syntheses still proceed under dynamic covalent control using electron‐deficient, heteroaryl, cycloalkyl, spiro, and even short alkenyl/alkynyl substrates. 
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