The intentional incorporation of group 13 and 15 elements into bulk silicon is a common way to tune its electronic properties. While this has revolutionized the semiconductor industry, introducing group 13 or 15 elements in nanoscale silicon-based molecules is less understood. A fundamental understanding of how the introduction of such elements (and the organic substituents on the element) effects the electronic properties of silicon is essential for rational design. Here, we report the synthesis of a series of N-aryl substituted cyclosilanes. Characterization of the frontier orbital energies by UV-vis spectroscopy and cyclic voltammetry suggest a trend between the substitution of the N-aryl <i>para-</i>position and the HOMO energy. Comparisons to calculated orbital density plots reveal the trigonal planar nitrogen has the ability to bridge the s-conjugated Si ring and the p-conjugated aromatic ring. Our results indicate that substitution of the <i>para</i>-position of the anilinic substituent enables the ability to tune the HOMO energy based on the electron donating/withdrawing ability of the substituent.

Tunable cyclic Si-N hybrid materials

2019 Fall National Meeting

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