5821-51-2Relevant articles and documents
Deca-heterosubstituted corannulenes
Pogoreltsev, Alla,Solel, Ephrath,Pappo, Doron,Keinan, Ehud
, p. 5425 - 5427 (2012)
The Cu(i)-catalyzed Ullmann condensation reaction between aliphatic alcohols and sym-pentachlorocorannulene provides a convenient entry to 1,3,5,7,9-pentaalkoxycorannulenes. The latter are easily converted to novel deca-heterosubstituted derivatives, such as 1,3,5,7,9-penta-X-2,4,6,8,10-penta- Y-corannulenes by electrophilic aromatic substitution.
Corannulene synthesis via the pyrolysis of silyl vinyl ethers
Liu, Charlie Z.,Rabideau, Peter W.
, p. 3437 - 3440 (1996)
The bis(trimethylsilyl enol ether) derived from 7,10-diacetylfluoranthene undergoes pyrolysis to afford corannulene. This is important in cases where the usual precursor, the bis(chlorovinyl) derivative, is not accessible from the diketone.
Transition metal complexes in organic synthesis, part 55. Synthesis of corannulene via an iron-mediated [2+2+1] cycloaddition
Knoelker, Hans-Joachim,Braier, Arnold,Broecher, Dirk J.,Jones, Peter G.,Piotrowski, Holger
, p. 8075 - 8078 (1999)
The synthesis of corannulene 2 in seven steps and 25% overall yield from 1,8-diiodonaphthalene 3 is reported.
Reversible phase transitions in a buckybowl monolayer
Merz, Leo,Parschau, Manfred,Zoppi, Laura,Baldridge, Kim K.,Siegel, Jay S.,Ernst, Karl-Heinz
, p. 1966 - 1969 (2009)
Like penguins on ice, buckybowl molecules move closer together when cooled on a copper surface (see model of a corannulene molecule adsorbed on Cu(111)). Upon heating, the molecules spread out into the original crystal phase again. The lower density at ro
Non-pyrolytic syntheses of buckybowls: Corannulene, cyclopentacorannulene, and a semibuckminsterfullerene
Sygula, Andrzej,Rabideau, Peter W.
, p. 7800 - 7803 (1999)
Corannulene (1), cyclopentacorannulene (2), and a C30H12 semibuckminsterfullerene (3) have been prepared by non-pyrolytic methods employing bromomethyl/dibromomethyl and/or dibromomethyl/dibromomethyl coupling with low-valent titanium or vanadium. Reductive coupling of tetrakis(dibromomethyl)-fluoranthene (8) with vanadium(III) chloride and lithium aluminum hydride affords corannulene in 70-75% yield. Similarly, hexakis(dibromomethyl)fluoranthene (13) leads to cyclopentacorannulene in 20-30% yield, and dodecabromo(octamethyl)indenofluoranthene (6) affords semibuckminsterfullerene (3) in 20% yield.
Stack the Bowls: Tailoring the Electronic Structure of Corannulene-Integrated Crystalline Materials
Rice, Allison M.,Dolgopolova, Ekaterina A.,Yarbrough, Brandon J.,Leith, Gabrielle A.,Martin, Corey R.,Stephenson, Kenneth S.,Heugh, Rebecca A.,Brandt, Amy J.,Chen, Donna A.,Karakalos, Stavros G.,Smith, Mark D.,Hatzell, Kelsey B.,Pellechia, Perry J.,Garashchuk, Sophya,Shustova, Natalia B.
, p. 11310 - 11315 (2018/08/11)
We report the first examples of purely organic donor–acceptor materials with integrated π-bowls (πBs) that combine not only crystallinity and high surface areas but also exhibit tunable electronic properties, resulting in a four-orders-of-magnitude conductivity enhancement in comparison with the parent framework. In addition to the first report of alkyne–azide cycloaddition utilized for corannulene immobilization in the solid state, we also probed the charge transfer rate within the Marcus theory as a function of mutual πB orientation for the first time, as well as shed light on the density of states near the Fermi edge. These studies could foreshadow new avenues for πB utilization for the development of optoelectronic devices or a route for highly efficient porous electrodes.
Superaromatic terpyridines based on corannulene responsive to metal ions
Wu, Difeng,Shao, Tao,Men, Jian,Chen, Xiaochuan,Gao, Guowei
supporting information, p. 1753 - 1761 (2014/01/06)
Two superaromatic terpyridine ligands (1 and 2) incorporating a corannulene unit at the 4′-position are reported. The optical and metal sensing properties of both ligands were investigated by the naked eye, and UV-vis and fluorescence spectroscopy in this work. In 1, the corannulene motif is directly connected to the 4′-phenylterpyridine domain, while in 2, the corannulene motif and the 4′-phenylterpyridine domain are separated by an acetylene linker. Both 1 and 2 can work as chemosensors for metal ions and display different optical responses to various metal ions. It is shown that both ligands exhibit a colorimetric sensing ability for Fe2+ through an obvious color change from colorless to magenta, and this color change can be observed easily by the naked eye. The addition of Fe2+ also leads to significant changes in the absorption spectra of the ligands. A characteristic red shift in the emission spectra is observed in the presence of Zn 2+, which facilitates the discrimination of Zn2+ from other metal ions. In addition, density functional theory (DFT) and time-dependent-density functional theory (TD-DFT) calculations were performed and shown to be consistent with the observed experimental results. The Royal Society of Chemistry.
