191-24-2Relevant articles and documents
REDUCTIVE RING CLOSURE OF HELICENES
Ayalon, Ari,Rabinovitz, Mordecai
, p. 2395 - 2398 (1992)
Reduction of -helicene (1) by alkali metal in THF yields a closed condensed polycyclic dianion i.e. benzoperylene dianion (3=).The ring closure reaction takes place via dihydro intermediate (2=).
Probing Diels-Alder reactivity on a model CNT sidewall
Jackson, Evan P.,Sisto, Thomas J.,Darzi, Evan R.,Jasti, Ramesh
, p. 3754 - 3758 (2016)
We have synthesized a cycloparaphenylene containing a perylene motif that is a model for a carbon nanotube sidewall. The reactivity of the sidewall model towards a Diels-Alder reaction using a masked acetylene was examined and similar reactivity was observed between the macrocyclic and planar substrate. This study suggests that a Diels-Alder reaction is a viable method for carbon nanotube growth using an appropriate template.
ORGANIC COMPOUND, THREE-DIMENSIONAL ORGANIC FRAMEWORK FORMED BY USING ORGANIC COMPOUND, SEPARATION SIEVE AND OPTICAL LAYER, WHICH COMPRISE ORGANIC FRAMEWORK, AND OPTICAL DEVICE COMPRISING OPTICAL LAYER AS OPTICAL AMPLIFICATION LAYER
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Paragraph 0356; 0359; 0360, (2019/02/13)
An organic compound, a three-dimensional organic structure formed by using the organic compound, a separation sieve and an optical layer having the organic structure, and an optical device having the optical layer as an optical amplification layer are provided. The organic structure includes a plurality of organic molecules self-assembled by non-covalent bonding. Each of the unit organic molecules has an aromatic ring, a first pair of substituents being connected to immediately adjacent positions of substitutable positions of the aromatic ring, and a second pair of substituents being connected to immediately adjacent positions of remaining substitutable positions of the aromatic ring. The unit organic molecules are self-assembled by van der Waals interaction, London dispersion interaction or hydrogen bonding between the first and the second pairs of the substituents and by pi-pi interactions between the aromatic rings.
Organic compound and 3-dimensional organic framework formed using the same
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, (2018/07/07)
Provided is a three-dimensional organic framework. The organic framework comprises a plurality of organic molecules which are self-assembled by non-covalent bonds. Each of the organic molecules comprises: a first pair of substituents which are each bound to an aromatic ring and to immediately adjacent positions among substitutable positions of the aromatic ring; and a second pair of substituents which are each bound to immediately adjacent positions among the rest of the substitutable positions. The organic molecules are self-assembled through Van Der Waals interactions, London dispersion interactions, or hydrogen bonding between the first and second pairs of the substituents, and andpi;-andpi; interactions between the aromatic rings.COPYRIGHT KIPO 2018
Facile photochemical synthesis of 5,10-disubstituted [5]helicenes by removing molecular orbital degeneracy
Ito, Natsuki,Hirose, Takashi,Matsuda, Kenji
supporting information, p. 2502 - 2505 (2014/05/20)
Photocyclodehydrogenation is a key reaction to synthesize helicenes; however, because of overannulation, it is not applicable to the synthesis of [5]helicene. Introduction of a cyano group was found to remove the orbital degeneracy of the low-lying unoccupied MOs; consequently, the lowest excitation comprises a single transition involving the C2-antisymmetric MO. Therefore, the problematic overannulation can be effectively suppressed. Moreover, in combination with the Knoevenagel reaction, a one-pot synthesis of 5,10-dicyano[5]helicene with 67% yield was accomplished.
Benzannulated cycloheptanones from binaphthyl platforms
Pieters, Gregory,Sbargoud, Kamal,Bridoux, Alexandre,Gaucher, Anne,Marque, Sylvain,Bourdreux, Flavien,Marrot, Jerome,Flot, David,Wantz, Guillaume,Dautel, Olivier,Prim, Damien
supporting information, p. 490 - 497 (2013/02/25)
Preparations of benzannulated cycloheptanones starting from unique binaphthyl molecular platforms are described. Binaphthyl acetic acids proved suitable percursors for fused cycloheptanone architectures. Seven-membered rings embedded in binaphthyl units were selectively generated by use of Eaton's reagent. Isomeric helical architectures arising from electrophilic cyclisation processes at second reaction sites in the precursors could also be obtained under different acidic conditions. Unambiguous discrimination between isomeric geometries was provided by multiple quantum NMR sequences. DFT calculations were performed and gave evidence of different behaviour of the substrates towards intramolecular electrophilic substitution. The theoretical approach confirmed the experimental results, agreeing completely with X-ray data. Preparations of benzannulated cycloheptanones starting from binaphthyl molecular platforms are described. Copyright
Synthesis of [5]helicenes with a substituent exclusively on the interior side of the helix by metal-catalyzed cycloisomerization
Yamamoto, Kosuke,Okazumi, Mieko,Suemune, Hiroshi,Usui, Kazuteru
supporting information, p. 1806 - 1809 (2013/06/04)
[5]Helicenes with a substituent exclusively oriented toward the interior curvature of the helix are synthesized by metal-catalyzed cycloisomerization. In addition, novel azulene-fused helicenes have been found through cycloisomerization studies. These [5]helicenes shows a high enough configurationally stability to allow resolution by HPLC on a chiral stationary phase.
Fluorescent coronene monoimide gels via H-bonding induced frustrated dipolar assembly
Jain, Ankit,Rao, K. Venkata,Kulkarni, Chidambar,George, Anjana,George, Subi J.
supporting information; scheme or table, p. 1467 - 1469 (2012/03/11)
Two stage self-assembly of novel coronene monoimide (CMI) based gels that results in resurfacing of monomer emission in the aggregated state is reported. This process is attributed to a frustrated head-head dipolar assembly forced by hydrogen bonding.
Expeditious synthesis of helicenes using an improved protocol of photocyclodehydrogenation of stilbenes
Talele, Harish R.,Chaudhary, Anju R.,Patel, Parthiv R.,Bedekar, Ashutosh V.
experimental part, p. 15 - 37 (2011/06/19)
An improved procedure has been developed for photodehydrocyclization of stilbenes for the synthesis of phenanthrenes and helicenes. This procedure involves the use of THF as a scavenger of hydriodic acid produced during iodine mediated photodehydrocyclization. The use of THF is advantageous due to its higher boiling point, lower cost and easy availability as compared to propylene oxide. The method is applied to synthesize a number of phenanthrenes and helicenes. ARKAT-USA, Inc.
One-step conversion of aromatic hydrocarbon bay regions into unsubstituted benzene rings: A reagent for the low-temperature, metal-free growth of single-chirality carbon nanotubes
Fort, Eric H.,Scott, Lawrence T.
supporting information; experimental part, p. 6626 - 6628 (2010/10/21)
A tube ride: The controlled chemical synthesis of uniform, single-walled carbon nanotubes from short hydrocarbon templates, such as aromatic belts and geodesic nanotube end-caps, by a Diels-Alder cycloaddition/rearomatization strategy requires a potent masked acetylene capable of transforming hydrocarbon bay regions into new unsubstituted benzene rings in a single operation. Nitroethylene has been found to effect such benzannulations (see scheme).
