The trianion has also been reported.[4] Electron transport properties have been investigated [5][6] as well as
carbon NMR[7]
Derivatives
Sumanene derivatives [8] such as naphtosumanene[9] and trisialsumanene[10][11] have been described. Chiral sumanenes are of some interest with respect to
inherent chirality,[12] examples are chiral trimethylsumanene[13] and a chiral sumanene cyclopentadienyl iron complex [14]
References
^Towards the design of tricyclopenta [def, jkl, pqr] triphenylene (sumanene): a bowl-shaped hydrocarbon featuring a structural motif present in C60 (buckminsterfullerene)Goverdhan Mehta, Shailesh R. Shah and K. Ravikumar Journal of the Chemical Society,
Chemical Communications, 1993, (12), 1006 - 1008
doi:
10.1039/C39930001006
^A Synthesis of Sumanene, a Fullerene Fragment Hidehiro Sakurai, Taro Daiko, and Toshikazu Hirao
Science, Vol 301, Issue 5641, 1878 , 26 September 2003doi:
10.1126/science.1088290
^Structural Elucidation of Sumanene and Generation of Its Benzylic Anions Hidehiro Sakurai, Taro Daiko, Hiroyuki Sakane, Toru Amaya, and Toshikazu Hirao
J. Am. Chem. Soc., 127 (33), 11580 -11581, 2005doi:
10.1021/ja0518169
^Anisotropic Electron Transport Properties in Sumanene Crystal Toru Amaya, Shu Seki, Toshiyuki Moriuchi, Kana Nakamoto, Takuto Nakata, Hiroyuki Sakane, Akinori Saeki, Seiichi Tagawa and Toshikazu Hirao J. Am. Chem. Soc., 2009, 131 (2), pp 408–409
doi:
10.1021/ja805997v
^The electrochemical inspection of the redox activity of sumanene and its concave CpFe complex Piero Zanello, Serena Fedi, Fabrizia Fabrizi de Biani, Gianluca Giorgi, Toru Amaya, Hiroyuki Sakane and Toshikazu Hirao
Dalton Trans., 2009, 9192-9197
doi:
10.1039/B910711H
^Solid-state 13C NMR investigations of 4,7-dihydro-1H-tricyclopenta[def,jkl,pqr]triphenylene (sumanene) and indeno[1,2,3-cd]fluoranthene: Buckminsterfullerene moieties Merrill D. Halling, Anita M. Orendt, Mark Strohmeier, Mark S. Solum, Vikki M. Tsefrikas, Toshikazu Hirao, Lawrence T. Scott, Ronald J. Pugmire and David M. Grant Phys. Chem. Chem. Phys., 2010, 12, 7934-7941
doi:
10.1039/C001903H
^Bowl-to-bowl inversion of sumanene derivatives Toru Amaya, Hiroyuki Sakane, Toshiko Muneishi and Toshikazu Hirao Chem. Commun., 2008, 765-767
doi:
10.1039/B712839H
^Synthesis of Highly Strained π-Bowls from Sumanene Toru Amaya, Takuto Nakata and Toshikazu Hirao, Japan J. Am. Chem. Soc., 2009, 131 (31), pp 10810–10811
doi:
10.1021/ja9031693
^Communication Development of a Sila-Friedel−Crafts Reaction and Its Application to the Synthesis of Dibenzosilole Derivatives Shunsuke Furukawa, Junji Kobayashi and Takayuki Kawashima J. Am. Chem. Soc., 2009, 131 (40), pp 14192–14193
doi:
10.1021/ja906566r
^Synthesis, structures and optical properties of trisilasumanene and its related compounds Tomoharu Tanikawa, Masaichi Saito, Jing Dong Guo and Shigeru Nagase Org. Biomol. Chem., 2011, 9, 1731-1735
doi:
10.1039/C0OB00987C
^Asymmetric Synthesis of a Chiral Buckybowl, Trimethylsumanene Shuhei Higashibayashi and Hidehiro Sakurai J. Am. Chem. Soc., 2008, 130 (27), pp 8592–8593
doi:
10.1021/ja802822k
^Sakane, H., Amaya, T., Moriuchi, T. and Hirao, T. (2009), A Chiral Concave-Bound Cyclopentadienyl Iron Complex of Sumanene. Angewandte Chemie International Edition, 48: 1640–1643.
doi:
10.1002/anie.200805567