Ylidic Substituents for Electron Rich Organic Materials with Synthetic and Energy Storage Applications

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Modification of the properties of a compound can be achieved by careful selection of the substituents, the groups attached to the parent structure. Among the multitude of substituents, amino groups, by virtue of their strong pi-donating properties, have been the most heavily used in applications where a more electron rich parent structure is required. We have recently demonstrated that, in contrast to the widespread belief that amino groups are the premier pi-donor substituent, iminophosphorano substituents (R3P=N-) are even stronger in this regard. We exploited this property to prepare the most powerful neutral organic electron donors, which act as homogeneous reducing agents. In complementarity to metal-based reagents, such organic reducing agents hold the promise of allowing for alternate reaction pathways, more mild conditions, and less environmental load. Nevertheless, substrate scope is limited and the reducing strength of many metal reagents greatly surpasses what is possible with the best organic reductants.