Halogen bonding is a unique and relatively unexplored noncovalent interaction that has recently garnered considerable attention due to its applications in materials development. The potential of eight halogen bond donors with three different electron withdrawing groups as molecular building blocks in organic optoelectronic devices is evaluated using a combination of Raman spectroscopy and computational chemistry. Trends are identified that connect donor strength directly to molecular structure, with particular emphasis on the C-I bond strength. As the electron withdrawing strength of the substituents in the halogen bond donor increases, the C-I stretch is observed to red-shift, suggesting a stronger sigma hole and a greater binding energy with halogen bond acceptors. Co-crystals formed from the most promising donor and acceptor molecules support this observation and reveal that the addition of nitro groups significantly enhances the halogen bond strength and potential of such building blocks in device applications.

Raman spectroscopic and computational study of the electron withdrawing effects on halogen bonding

253rd National Meeting (2017)

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