A series of conjugated organic compounds including thiophenes, ladder oligomers and diarayl polyenes have been synthesized and characterized. In this presentation we report on series of structurally related molecules in the above categories and examine the impact various molecular modifications on the observed crystal packings. Twenty eight single crystal structures are considered in this report. Single crystal structural analysis reveals that one can develop general guidelines to carefully modify molecular structures to induce planarity and enhance π-stacking ability in these materials. Specifically, the introduction of strong electron acceptors such as nitro-, cyano-, tricyanovinyl- and dicyanovinyl- groups works well in promoting planarity (with an exception of polyenes) and π-stack formation. We also will present our findings on optical properties and DFT calculations. <i>Inter</i>- and intramolecular interactions in observed in these materials will be the focus of this presentation. Finally our attempts at minimizing the torsion between adjacent aryl rings through intramolecular interactions (CN…S and CN…H) will be presented.<br/>

Promoting molecular planarity and solid state state π-stack formation in conjugated organic materials

251st National Meeting (2016)

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