Creation of hoop- and bowl-shaped benzenoid systems by selective detraction of [60]fullerene conjugation. [10]cyclophenacene and fused corannulene derivatives

Journal of the American Chemical Society
Yutaka MatsuoEiichi Nakamura

Abstract

Selective penta-addition of a methylcopper reagent followed by addition of a phenylcopper reagent to a suitably modified synthetic intermediate results in creation of 40pi-electron systems-hoop- and bowl-shaped cyclic benzenoid compounds, [10]cyclophenacene, and dibenzo-fused corannulene derivatives. The 40pi-electron cyclophenacene derivatives have been found to be chemically stable, yellow-colored, luminescent (560 nm), and EPR-silent. X-ray crystallographic analysis provided precision structural data sets. The dibenzo-fused corannulene derivatives exhibit blue-green (460 nm) to red (649 nm) fluorescence.

References

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Citations

Apr 11, 2013·Chemical Reviews·Manolis D Tzirakis, Michael Orfanopoulos
Sep 29, 2011·Physical Chemistry Chemical Physics : PCCP·Alexandru T Balaban
Oct 26, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Yutaka MatsuoEiichi Nakamura
Mar 10, 2016·Organic Letters·Yasutomo SegawaKenichiro Itami
May 3, 2016·Journal of the American Chemical Society·Matthew R GolderRamesh Jasti
Mar 24, 2017·Angewandte Chemie·Allison M RiceNatalia B Shustova
Feb 24, 2015·Physical Chemistry Chemical Physics : PCCP·Birgit Esser
Jan 1, 2008·Chemistry : a European Journal·Chagit DenekampA Dieter Schlüter
Jan 13, 2009·Chemistry, an Asian Journal·Takahiro NakaeEiichi Nakamura
Feb 21, 2009·Chemistry : a European Journal·Masakazu Nambo, Kenichiro Itami
Mar 13, 2009·Chemistry : a European Journal·Stefan C KornmayerRolf Gleiter
Jul 10, 2009·Angewandte Chemie·Hiroko TakabaKenichiro Itami
Jun 10, 2010·Chemical Society Reviews·David EisenbergMordecai Rabinovitz
Apr 20, 2012·Chemical Communications : Chem Comm·Keita HagiwaraMichito Yoshizawa
Mar 13, 2009·Chemistry : a European Journal·Birgit EsserRolf Gleiter
Jan 15, 2011·Physical Review. E, Statistical, Nonlinear, and Soft Matter Physics·Matthieu Marechal, Marjolein Dijkstra
Sep 10, 2020·Angewandte Chemie·Mathias HermannBirgit Esser
Feb 28, 2009·Organic Letters·Simon ClavagueraYves Rubin
Nov 10, 2009·Journal of the American Chemical Society·Chang-Zhi LiEiichi Nakamura
May 28, 2009·Accounts of Chemical Research·Rolf GleiterStefan C Kornmayer
Jan 14, 2009·Organic Letters·Stefan C KornmayerRolf Gleiter
Apr 15, 2010·Nano Letters·Matthieu MarechalMarjolein Dijkstra
Apr 20, 2010·Journal of the American Chemical Society·Yutaka MatsuoEiichi Nakamura
Jul 26, 2008·Chemical Reviews·Yutaka Matsuo, Eiichi Nakamura
Apr 17, 2021·Nature Chemistry·Qing-Hui GuoJ Fraser Stoddart
Nov 5, 2011·Organic Letters·Elizabeth S HirstRamesh Jasti
Feb 23, 2019·Journal of the American Chemical Society·Xuelin YaoKlaus Müllen
Feb 18, 2015·Accounts of Chemical Research·Matthew R Golder, Ramesh Jasti
Jul 24, 2018·Journal of the American Chemical Society·Guillaume PovieKenichiro Itami
Jul 27, 2006·Journal of the American Chemical Society·Yutaka MatsuoEiichi Nakamura
Dec 15, 2006·Chemical Reviews·Carlo Thilgen, François Diederich
Dec 15, 2006·Chemical Reviews·Kazukuni Tahara, Yoshito Tobe
Feb 24, 2007·Journal of the American Chemical Society·Yu-Wu ZhongEiichi Nakamura
Jan 6, 2005·Journal of the American Chemical Society·Yasuyuki NakamuraAtsuhiro Osuka
May 8, 2008·Journal of the American Chemical Society·Birgit EsserRolf Gleiter
Jun 1, 2006·Journal of the American Chemical Society·Yutaka MatsuoEiichi Nakamura

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