Browsing by Author "Morgan, Matthew M."
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- ItemOpen AccessEfficient Synthetic Methods for the Installation of Boron-Nitrogen Bonds in Conjugated Organic Molecules(Royal Society of Chemistry, 2015-11-06) Piers, Warren E.; Morgan, Matthew M.Polycyclic aromatic hydrocarbons in which one or more CC units have been replaced by isoelectronic BN units have attracted interest as potentially improved organic materials in various devices. This promise has been hampered by a lack of access to gram quantities of these materials. However, the exploitation of keystone reactions such as ring closing metathesis, borylative cyclization of amino styrenes and electrophilic borylation has lead to strategies for access to workable amounts of material. These strategies can be augmented by judicious postfunctionalization reactions to diversify the library of materials available. This Frontier article highlights some of the recent successes and shows that the long promised applications of BN-doped PAHs are beginning to be explored in a meaningful way.
- ItemOpen AccessZirconocene-based methods for the preparation of BN indenes: application to the synthesis of 1,5-dibora-4a,8a-diaza-1,2,3,5,6,7-hexaaryl-4,8-dimethyl-s-indacenes.(American Chemical Society, 2017-03-08) Piers, Warren E.; Morgan, Matthew M.; Patrick, Evan A.; Rautiainen, J. Mikko; Tuononen, Heikki M.; Spasyuk, Denis M.A method for the preparation of 3-bora-9-azaindene heterocycles based on zirconocene-mediated functionalization of the o-CH bonds of pyridines has been developed and used to make two such compounds. Unlike other methods, the boron center in these heterocycles remains functionalized with a chloride ligand, and so the compounds can be further elaborated through halide abstraction and reduction. The utility of the method was further demonstrated by applying it toward the preparation of 1,5-dibora-4a,8a-diaza BN analogues of the intriguing hydrocarbon s-indacene starting from 2,5-dimethylpyrazine. Gram quantities of one such compound were prepared and fully characterized, and both experimental and computational data are presented to compare its properties to those of the parent hydrocarbon s-indacene. These data indicate that the BN-substituted derivative exhibits lowered aromaticity in relation to the hydrocarbon.