1092522-75-2Relevant academic research and scientific papers
Concise synthesis and crystal structure of [12]cycloparaphenylene
Segawa, Yasutomo,Miyamoto, Shinpei,Omachi, Haruka,Matsuura, Sanae,Senel, Petr,Sasamori, Takahiro,Tokitoh, Norihiro,Itami, Kenichiro
, p. 3244 - 3248 (2011)
Crystal clear: The title macrocycle was constructed by a nickel-mediated shotgun macrocyclization. The X-ray crystallographic structure of [12]CPP revealed a circular structure incorporating two cyclohexane molecules within the ring. The [12]CPP molecules
Selective and random syntheses of [n]cycloparaphenylenes (n = 8-13) and size dependence of their electronic properties
Iwamoto, Takahiro,Watanabe, Yoshiki,Sakamoto, Youichi,Suzuki, Toshiyasu,Yamago, Shigeru
, p. 8354 - 8361 (2011)
[n]Cycloparaphenylenes (n = 8-13, CPPs) were synthesized, and their physical properties were systematically investigated. [8] and [12]CPPs were selectively prepared from the reaction of 4,4′-bis(trimethylstannyl) biphenyl and 4,4′-bis(trimethylstannyl)terphenyl, respectively, with Pt(cod)Cl2 (cod = 1,5-cyclooctadiene) through square-shaped tetranuclear platinum intermediates. A mixture of [8]-[13]CPPs was prepared in good combined yields by mixing biphenyl and terphenyl precursors with platinum sources. Products were easily separated and purified by using gel permeation chromatography. In 1H NMR spectra, the proton of the CPPs shifts to a lower field as n increased due to an anisotropic effect from the nearby PP moieties. Although the UV-vis spectra were rather insensitive to the size of the CPPs, the fluorescence spectra changed significantly in relation to their size. A larger Stokes shift was observed for the smaller CPPs. Redox properties of the CPPs were measured for the first time by using cyclic voltammetry, and the smaller CPPs had lower oxidation potentials. The results are consistent with the HOMO energies of CPPs, of which the smaller CPPs had higher energies.
Topological molecular nanocarbons: All-benzene catenane and trefoil knot
Segawa, Yasutomo,Kuwayama, Motonobu,Hijikata, Yuh,Fushimi, Masako,Nishihara, Taishi,Pirillo, Jenny,Shirasaki, Junya,Kubota, Natsumi,Itami, Kenichiro
, p. 272 - 276 (2019/08/07)
The generation of topologically complex nanocarbons can spur developments in science and technology. However, conventional synthetic routes to interlocked molecules require heteroatoms. We report the synthesis of catenanes and a molecular trefoil knot con
Practical Synthesis of [n]Cycloparaphenylenes (n=5, 7-12) by H2SnCl4-mediated aromatization of 1,4-dihydroxycyclo-2,5-diene Precursors
Patel, Vijay Kumar,Kayahara, Eiichi,Yamago, Shigeru
, p. 5742 - 5749 (2015/03/31)
Cyclic precursors of cycloparaphenylenes (CPPs) containing 1,4-dihydroxy-2,5-cyclohexadien-1,4-diyl units are prepared by modifying a synthetic method developed by Jasti and co-workers for the synthesis of corresponding 1,4-dimethoxy derivatives. Reductive aromatization of the diyl moieties by SnCl2/2 HCl takes place under mild conditions and affords the CPPs in good yields, incorporating 5 or 7-12 phenylene units. Highly strained [5]CPP is synthesized in greater than 0.3 g scale. 119Sn NMR spectroscopy clarifies the in situ formation of an ate complex, H2SnCl4, upon mixing a 2:1 ratio of HCl and SnCl2, which serves as a highly active reducing agent under nearly neutral conditions. When more than 2 equivalents of HCl, in relation to SnCl2, are used, acid-catalyzed decomposition of the CPP precursors takes place. The stoichiometry of HCl and SnCl2 is critical in achieving the desired aromatization reaction of highly strained CPP precursors. Behold the ring of rings: [n]Cycloparaphenylenes (n=5, 7-12) have been synthesized in good yields by reductive aromatization of cyclic precursors incorporating 1,4-dihydroxycyclo-2,5-diene units by employing H2SnCl4, which was prepared in situ by mixing SnCl2 and 2 equivalents of concentrated aqueous HCl.
CARBON NANORING AND METHOD FOR PRODUCING A RING-SHAPED COMPOUND SUITABLE AS A STARTING MATERIAL FOR PRODUCTION OF THE SAME
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Paragraph 0195; 0197, (2013/03/26)
The present invention produces Cyclic Compound (1) in which organic ring groups including cyclohexane rings and benzene rings are continuously bonded, using a compound having at least one cyclohexane ring and benzene rings with halogen atoms at the two te
CYCLOPARA(HETERO)ARYLENE COMPOUND AND METHOD FOR PRODUCING SAME
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Page/Page column 20-21, (2012/08/14)
Provided are a cyclopara(hetero)arylene compound and a method for producing the same. More specifically, provided is a cycloparaphenylene compound represented by Formula (I): wherein Ar1, Ar2, Ar3, and Ar4 are the same or different, and represent an optionally substituted divalent aromatic group or an optionally substituted divalent heteroaromatic group, and n1, n2, n3, and n4 are the same or different, and represent an integer of 1 or more.
CARBON NANOHOOPS AND METHODS OF MAKING
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Page/Page column 8, (2011/07/29)
The present invention provides cycloparaphenylene compounds, their macrocyclic precursors, and methods for making the compounds. The cycloparaphenylene compounds can be used to prepare armchair carbon nanotubes.
