Bradley Rose - Synthesis, Crystal Structures, and Photophysical Properties of Electron-Accepting Diethynylindenofluorenediones

Version 1

      Publication Details (including relevant citation   information):

      Rose, Bradley D., Chase, Daniel T., Weber, Christopher D.,   Zakharov, Lev N., Lonergan, Mark C., Haley, Michael M.,   Organic Letters, 2011, 13 (8), 2106–2109

      Abstract:

      A series of   6,12-bis[(trialkylsilyl)ethynyl]indeno[1,2-b]fluorene-5,11-diones   has been synthesized. X-ray crystallographic analysis of these   compounds reveals that triisopropylsilyl (TIPS) substitution on   the alkyne terminus affords the largest number of intermolecular   π−π interactions in the solid state. Conversely, use of   trialkylsilyl groups smaller or larger than TIPS furnishes a   variety of crystal-packing motifs that contain fewer π−π   interactions. Electrochemical and photophysical data suggest that   these molecules are excellent electron-accepting materials.

      Address (URL): http://dx.doi.org/10.1021/ol200525g