Enhanced solid-state fluorescence in the oxadiazole-based excited-state intramolecular proton-transfer (ESIPT) material: Synthesis, optical property, and crystal structure

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We report highly fluorescent oxadiazole-based excited-state intramolecular proton-transfer (ESIPT) material, 2,5-bis-[5-(4-tert-butyl-phenyl)1,3,4]oxadiazol-2-yl] -phenol (SOX) in solid state film (Phi(f) = 0.47) as well as in solution (Phi(f) = 0.40). From the single crystal X-ray crystallography, a molecular geometry of SOX was found to be nearly planar due to the strong intramolecular hydrogen-bond between the hydroxyl and oxadiazole groups to give rise to the virtually single keto fluorescence. In view of the molecular arrangement, a specific dimer interaction caused by a Coulomb attraction in the SOX crystal was most likely associated with a sliding-away stacking, which contributed to the intense solid-state fluorescence. On the other hand, 2,5-bis-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl] -benzene-1,4-diol (DOX) with dual ESIPT sites but otherwise the same as SOX showed a significantly red-shifted orange emission (lambda(em) = 573nm) of keto tautomer relative to the bluish-green emission = 486 nm) of SOX in chloroform. Similarly, the fluorescence emission of DOX in solid-state film (Phi(f) = 0.13) was highly enhanced from that in solution (Phi(f) = 0.02). Interestingly, SOX and DOX showed well-defined room-temperature phosphorescence. Kinetic studies on the ESIPT keto fluorescence as well as the phosphorescence were investigated using picosecond laser experiments. (c) 2007 Elsevier B.V. All tights reserved.
Publisher
ELSEVIER SCIENCE SA
Issue Date
2007-09
Language
English
Article Type
Article
Citation

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, v.191, no.1, pp.51 - 58

ISSN
1010-6030
DOI
10.1016/j.jphotochem.2007.04.003
URI
http://hdl.handle.net/10203/282724
Appears in Collection
CBE-Journal Papers(저널논문)
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