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1 2008

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Hydrogen Bonding and Protonation Effects on Excited-state Electron Transfer in meta and para-Dialkylaminopyridines

Szydłowska I., Nowacki J., Zielińska A., Herbich J.

Polish Journal of Chemistry

2008

Vol. 82, nr 4

847-864

Synthetic, spectral and photophysical investigations were performed for a series of dialkylaminopyridines (DAAPs) representing electron donor-acceptor systems. 4-Dimethyl aminopyridine and its analogues, substituted by an electron donor at the para position of the acceptor ring, show solvent-dependent dual luminescence from the substrate (primary excited state) and the product (TICT state) of the photoinduced electron transfer process. The investigations in mixed solvents (n-hex ane + 1-butanol) allow us to prove that dual luminescence is observed for 1:1 complexes of 4-DAAPs with the alcohol molecule hydrogen-bonded to the pyridine nitrogen atom. Contrary to 4-DAAPs, the electronic structure and geometry of the fluorescent CT state of 3-diisopropyl amino-pyridine are solvent-dependent (this 1CT state does not correspond to a full separation of charges). The spectroscopic and photophysical properties of the protonated forms of DAAPs are also presented. It is note worthy that the monocations of 4-diisopropyl-aminopyridine exhibit TICT fluorescence.