4.6 Article

Regulation of p-Stacked Anthracene Arrangement for Fluorescence Modulation of Organic Solid from Monomer to Excited Oligomer Emission

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 15, 页码 4634-4643

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103518

关键词

crystal engineering; hydrogen bonds; p-stacked arrangements; organic salts; solid-state fluorescence

资金

  1. Japan Society for the Promotion of Science (JSPS)
  2. Global COE (center of excellence) Global Education and Research Center for Bio-Environmental Chemistry of Osaka University
  3. Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan [22685014, 22108517, 18039025]
  4. Grants-in-Aid for Scientific Research [22685014, 18039025, 24108723, 22108517, 09J00619, 24655124, 21245035] Funding Source: KAKEN

向作者/读者索取更多资源

The construction and precise control of the face-to-face p-stacked arrangements of anthracene fluorophores in the crystalline state led to a remarkable red shift in the fluorescence spectrum due to unprecedented excited oligomer formation. The arrangements were regulated by using organic salts including anthracene-1,5-disulfonic acid (1,5-ADS) and a variety of aliphatic amines. Because of the smaller number of hydrogen atoms at the edge positions and the steric effect of the sulfonate groups, 1,5-ADS should prefer face-to-face p-stacked arrangements over the usual edge-to-face herringbone arrangement. Indeed, as the alkyl substituents were lengthened, the organic salts altered their anthracene arrangement to give two-dimensional (2D) edge-to-face and end-to-face herringbone arrangements, one-dimensional (1D) face-to-face zigzag and slipped stacking arrangements, a lateral 1D face-to-face arrangement like part of a brick wall, and a discrete monomer arrangement. The monomer arrangement behaved as a dilute solution even in the close-packed solid state to emit deep blue light. The 1D face-to-face zigzag and slipped stacking of the anthracene fluorophores caused a red shift of 3040 nm in the fluorescence emission with respect to the discrete arrangement, probably owing to ground-state associations. On the other hand, the 2D end-to-face stacking induced a larger red shift of 60 nm, which is attributed to the excimer fluorescence. Surprisingly, the brick-like lateral face-to-face arrangement afforded a remarkable red shift of 150 nm to give yellow fluorescence. This anomalous red shift is probably due to excited oligomer formation in such a lateral 1D arrangement according to the long fluorescence lifetime and little shift in the excitation spectrum. The regulation of the p-stacked arrangement of anthracene fluorophores enabled the wide modulation of the fluorescence and a detailed investigation of the relationships between the photophysical properties and the arrangements.

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