Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 28, Pages 8051-8060Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700622
Keywords
conjugation; heterocycles; optical properties; pi interactions; X-ray crystallography
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Ladder-type pi-conjugated molecules bearing heteraborin (azaborine or thiaborin) units were synthesized, and X-ray crystallographic analysis of pentacene-type molecules showed that these molecules have rigid and planar structures. UV-visible spectroscopy and theoretical calculations revealed the enhancement of electronic interaction between heteraborin units, the decrease in HOMO-LUMO energy gaps, and the strong effect of the bridging main-group elements (nitrogen or sulfur) on the electronic states. The ladder-type molecules emitted strong fluorescence both in solution and in the solid state, and the emission-band shapes were different from each other, indicating the existence of intermolecular interactions in the solid state. Complex formation of the ladder molecules with fluoride ion was monitored by UV-visible spectroscopy, which revealed that the Lewis acidity of these molecules can be controlled by the elongation of it systems and the change of the bridging main-group elements.
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