2-(2′-Pyridyl)pyrroles: Part II. Spectroscopic investigation of pyridylpyrrole alcohol complexes

Abstract

A homologous series of 2-(2′-pyridyl)pyrroles were studied as a possible model system for intermolecular hydrogen bonding interactions in molecules that can act as both hydrogen bond donors and acceptors. Steady state spectroscopic methods were used to assess the importance of intermolecular hydrogen bonding interactions in dilute solutions of 2-(2′-pyridyl)pyrroles in the absence and presence of alcohols. The absorption and fluorescence properties of such solutions were investigated to determine the relevance of such hydrogen bonding interactions in the ground and excited state behavior of the 2-(2′-pyridyl)pyrroles. Over the concentration range studied, no evidence was found for the formation of hydrogen-bonded 2-(2′-pyridyl)pyrrole dimers. However, it was determined that 3,5-dimethyl-2-(2′-pyridyl)pyrrole forms weak (K ∼ 5–12 M−1) 1∶1 hydrogen-bonded complexes with methanol and t-butyl alcohol in the ground state, and 3,5-di-tert-butyl-2-(2′-pyridyl)pyrrole forms both 1∶1 and 1∶2 complexes with the same alcohols. Despite the formation of hydrogen-bonded 2-(2′-pyridyl)pyrrole alcohol complexes, no experimental evidence was found for excited state proton transfer in such complexes.