From Thia- to Selenadiazoles: Changing Interaction Priority
Organic Letters2013Vol. 15(3), pp. 666–669
Citations Over TimeTop 10% of 2013 papers
Benjamin Lindner, Benjamin A. Coombs, Manuel Schaffroth, Jens U. Engelhart, Olena Tverskoy, Frank Röminger, Manuel Hamburger, Uwe H. F. Bunz
Abstract
The synthesis, optical, and electrochemical properties as well as solid-state structures of a series of alkynylated, benzannulated selenadiazoles are reported. This set of compounds is compared to the lighter homologue series, the thiadiazoles. The selenadiazoles show head-to-head dimerization in the solid state, while packing of the thiadiazoles was dominated by the steric bulk of the side groups. The Se-N interaction is a supramolecular motif that should drive the effective self-assembly and modulate charge transport when these compounds are used as thin films in devices.
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