Hydrogen-bonded complexes of lumichrome.

Authors:
Ewa Sikorska
Ewa Sikorska
Poznań University of Economics
Poland
Maciej Kubicki
Maciej Kubicki
Adam Mickiewicz University
Aleksander Siemiarczuk
Aleksander Siemiarczuk
University of Guelph
Canada
Jacek Koput
Jacek Koput
Adam Mickiewicz University
Poznań | Poland

J Phys Chem A 2005 Mar;109(9):1785-94

Faculty of Commodity Science, Poznań University of Economics, al. Niepodleglości 10, 60-967 Poznań, Poland.

Hydrogen bonds were shown to play an important role in the lumichrome photophysics and photochemistry both in solutions and in the solid state. In solutions, lumichrome can form hydrogen-bonded complexes with a variety of molecules, such as acetic acid or methanol, as supported by spectral and equilibrium studies. Photoexcitation of some hydrogen-bonded complexes, having appropriate configuration, as in the case of acetic acid, may lead to excited-state proton transfer, resulting in formation of the isoalloxazinic structure, detectable by its characteristic emission, distinct from that of the intrinsically alloxazinic lumichrome. Theoretical calculations confirmed the role of the hydrogen-bonded complexes, yielding several stable eight-membered cyclic structures of such complexes characterized by spectral changes similar to those observed experimentally. Hydrogen bonds play an essential role in the formation of the lumichrome crystal structure, as follows from the X-ray diffraction results. Interestingly, the crystals studied included molecules of methanol used as solvent in crystal growth. The emission studies of polycrystalline samples, similar to the processes occurring in solutions, point to the importance of hydrogen-bonding interactions in crystal packing allowed by the symmetry of the hydrogen-bonded dimers.

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March 2005
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