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Creators/Authors contains: "Zocchi, Luca_J"

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  1. ; ; ; (, Chemistry – A European Journal)
    Abstract Fusion of aromatic subunits to stabilize an antiaromatic core allows the isolation and study of otherwise unstable paratropic systems. A complete study of a series of six naphthothiophene‐fuseds‐indacene isomers is herein described. Additionally, the structural modifications resulted in increased π–π overlap in the solid state, which was further explored through changing the sterically blocking mesityl group to (triisopropylsilyl)ethynyl in three derivatives. The computed antiaromaticity of the six isomers is compared to the observed physical properties, such as NMR chemical shift, UV‐vis, and CV data. We find that the calculations predict the most antiaromatic isomer and give a general estimation of the relative degree of paratropicity for the remaining isomers, when compared to the experimental results. 
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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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