Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 31, Pages 9577-9584Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801255
Keywords
exciplex; fluorine; organogel; pi-stacking; self-assembly
Categories
Funding
- Department of Science and Technology (DST: New Delhi India)
- CSIR [NWP0023]
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The arene-perfluoroarene (Ar-H-Ar-F) interaction. which has been extensively studied in the field of solid-state chemistry. is exploited in the hierarchical self-assembly of oligo(para-phenylenevinylcne)s (OPVs) with controlled longitudinal fiber growth that leads to gelation. The size of the self-assembled fibers of a pentafluorophenyl-functionalized OPV 5 could be controlled through C-F center dot center dot center dot H-C hydrogen bonding and pi stacking. The ability of fluoroaromatic compounds to form excited-state complexes with aromatic amines has been utilized to form a supramolecular exciplex, exclusively in the gel state, that exhibits enhanced emission. Thus, the commonly encountered fluorescence quenching during the self-assembly of OPVs could be considerably prevented by exciplex formation with N.N-dimethylaniline (DMA), which only occurred for the fluorinated OPV and not for the non-fluorinated analogue 4. In the former case, a threefold enhancement in the emission intensity Could be observed in the gel state, whereas no change in emission occurred in solution. Thus. the major limitations of spontaneous fiber growth and fluorescence self-quenching encountered in the self-assembly of OPVs could be controlled to a great extent by using the Versatile Ar-H-Ar-F interaction.
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