Large planar aromatic molecules such as anthracenes and carbazoles often pack in parallel planar face-to-face or 'T-shaped' face-to-edge interactions, among others, in the solid state and even in the gas phase However, the optimum geometry of the dimers in solution probably contains a face-to-face orientation of the aromatic rings in order to maximize p overlap, as found for the excited state dimers (excimers) of anthracene although a nonparallel planar interaction more akin to the orientation of the two anthryl groups in di(9-anthryl)methane also has been proposed.Association of aryl groups in diarylalkanes can be more favorable entropically than those which occur intermolecularly, but the connecting linkage can also restrict the geometries possible for interaction. In particular, dimers with aryl groups separated by three saturated carbons seem optimally situated to achieve parallel planar interactions. Such as 1, 3-diarylalkanes have been used to model the behavior of pendant aryl groups in organic polymers such as poly(vinylcarbazole) and poly(vinylanthracene). These polymers become photochemical semiconductors in the presence of electron accepting dopants. Since the tacticity of the polymer will affect the interactions which occur between the carbazoles units, we prepared meso-2, 4-di(N-carbazolyl)pentane in order to determine the effect of the stereochemistry of the carbazole groups on the close contacts between them.

Synthesis of di-and tri-aryl pentanes as model for conducting organic polymers

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.