2011
DOI: 10.1246/cl.2011.423
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[9]Cycloparaphenylene: Nickel-mediated Synthesis and Crystal Structure

Abstract: Nickel-mediated synthesis of [9]cycloparaphenylene ([9]CPP) is described. L-shaped diphenylcyclohexane monomers underwent cyclotrimerization under the influence of [Ni(cod) 2 ]/bipy. X-ray crystal-structure analysis and VT NMR analysis of the thus-formed cyclic trimer confirmed its triangle structure and interesting cyclohexane-flipping behavior in solution. Cyclic trimer was converted to [9]CPP by acidmediated aromatization. The first X-ray crystal structure of [9]CPP is also described.Highly symmetric macroc… Show more

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Cited by 150 publications
(132 citation statements)
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“…In the above mentioned works, it was possible to obtain CPPs in the milligram-scale, with Jasti and co-workers [6,14] producing the first gram-scale synthesis. [16,17] The molecules self-assemble in a herringbone (HB) pattern independently of their size, as it often happens for other π-conjugated systems. [16,17] The molecules self-assemble in a herringbone (HB) pattern independently of their size, as it often happens for other π-conjugated systems.…”
mentioning
confidence: 99%
See 1 more Smart Citation
“…In the above mentioned works, it was possible to obtain CPPs in the milligram-scale, with Jasti and co-workers [6,14] producing the first gram-scale synthesis. [16,17] The molecules self-assemble in a herringbone (HB) pattern independently of their size, as it often happens for other π-conjugated systems. [16,17] The molecules self-assemble in a herringbone (HB) pattern independently of their size, as it often happens for other π-conjugated systems.…”
mentioning
confidence: 99%
“…[16,17] The molecules self-assemble in a herringbone (HB) pattern independently of their size, as it often happens for other π-conjugated systems. [16,17] The molecules self-assemble in a herringbone (HB) pattern independently of their size, as it often happens for other π-conjugated systems.…”
mentioning
confidence: 99%
“…Daher entwickelte Itami 2011 ein stringenteres Verfahren zur Synthese von [9]CPP und [12]CPP (Schema 15). [30] Die durch Ni(cod) 2 /bpy (cod = 1,5-Cyclooctadien, bpy = 2,2'-Bipyridyl) vermittelte Homokupplung der L-fçrmigen Einheiten 59 a bzw. …”
Section: Cycloparaphenyleneunclassified
“…The ring size and substitution patterns of the polyarylated [n]CPPs were varied to overcome strain-induced side reactions during the oxidative cyclodehydrogenation and cyclic para-hexa-peri-hexabenzocoronene trimers ([3]CHBCs) were selectively obtained. [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] A further extension of the p system, as an approach towards CNT segments,can be achieved by pre-and post-construction Figure 1. Thep roperties of PA Hs strongly depend on the size and shape,being controlled by the bottom-up approach to access one-dimensional (1D) or 2D PA Hs,s uch as graphene nanoribbons (GNRs) [1][2][3][4][5] and nanographenes (NGs).…”
mentioning
confidence: 99%