Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 12, Issue 30, Pages 7827-7838Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200600094
Keywords
crystal structures; dyes/pigments; fluorescence; heterocycles; substituent effects
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Novel heterocyclic quinol-type fluorophores (4a-c) and (5a-c) that contain substituents (R = Me, Bu, Ph) with nonconjugated linkages to the chromophore skeleton have been synthesized and their photophysical properties have been investigated in solution and in the solid state. Considerable differences in the absorption and fluorescence spectra were observed between the two states. Quinols 4a-c and 5a-c exhibited almost the same absorption and fluorescence spectra in solution; however, their solid-state fluorescence excitation and emission spectra in the crystalline state were quite different. We performed X-ray crystallographic analyses to elucidate the dramatic effect of the substituents of the nonconjugated linkage on the solid-state fluorescence excitation and emission spectra. The relationships between the solid-state photophysical properties and the chemical and crystal structures of 4a-c and 5a-c are discussed on the basis of the X-ray crystal structures.
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