A General Synthesis of Disubstituted Rubicenes

Smet, Mario; Shukla, R. C.; Fülöp, Lívia; Dehaen, Wim

doi:10.1002/(sici)1099-0690(199812)1998:12<2769::aid-ejoc2769>3.0.co;2-7

Cited by 32 publications

(16 citation statements)

References 11 publications

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“…The synthesis was performed using previously established platinum‐mediated macrocyclization methods . Rubicene with two boryl groups ( 2 ) at the 5‐ and 12‐positions was prepared from dichlororubicene ( 1 ) by Miyaura borylation and subjected to the Pt‐mediated macrocyclization (Scheme ) . Without isolation of the macrocyclic Pt complexes, subsequent reductive elimination was performed after ligand exchange with PPh 3 to afford [ n ]CR.…”

Section: Figurementioning

confidence: 99%

Pentagon‐Embedded Cycloarylenes with Cylindrical Shapes

et al. 2017

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Cylinder-shaped graphitic networks in carbon nanotubes have attracted interest from scientists in various disciplines. The chemical synthesis of segments thereof is considered as a challenging and appealing subject in chemistry, and deepens our understanding of curved and conjugated arrays of hexagons. We herein report the synthesis of cylinder-shaped molecules containing non-hexagon bridges in their conjugated systems. Multiple pentagon units were embedded in the cylinder-shaped discrete molecules, and the stereoisomerism originating from their helical carbon arrangements was studied. Structural analysis by NMR, UV/Vis absorption spectroscopy, and single-crystal X-ray diffraction provided fundamental experimental information on the curved systems with conjugation across the pentagons. This study provides the first experimental guide for further explorations of anomalous non-hexagon arrays of graphitic carbon materials with cylindrical shapes.

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Section: Figurementioning

confidence: 99%

Pentagon‐Embedded Cycloarylenes with Cylindrical Shapes

et al. 2017

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“…In previous work we have reported the preparation and alkylation of 5,12-dihydroxyrubicene [1][2]. Although alkylation of the latter compound with benzyl bromides proceeded quite smoothly, reaction of this rubicene derivative with simple aliphatic bromides and tosylates turned out to fail.…”

Section: Resultsmentioning

confidence: 99%

“…Recently we have used the highly fluorescing and photostable rubicene as a core in dendrimer chemistry [1]. A new approach towards disubstituted rubicenes was devised [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Crown Ethers Containing a Rubicene Moiety

Smet

Dehaen

2000

Molecules

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“…Being inspired by an interesting heptacyclic arene of rubicene [6], we decided to start a new program focused on the synthesis of annulated analogues of azafluoranthene and heteroazulene, starting from the dervatives of PQ [7]. During our preliminary studies we observed the possibility from the same starter, i.e.…”

Section: Dpipq Cpdppq Ptnamentioning

confidence: 93%

From pirazoloquinolines to annulated analogues of azafluoranthene and azulene dyes: UV-VIS spectroscopy and quantum chemical study

Całus¹,

Danel

Uchacz

et al. 2009

2009 3rd ICTON Mediterranean Winter Conference (ICTON-MW)

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Paper reports the measured optical absorption and fluorescence spectra of 4-(2-chlorophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline (CPDPPQ), as well as 1,3-diphenyl-3H-indeno[1,2,3-de]pyrazolo[3,4-b]quinoline (DPIPQ) and 6-phenyl- 6H-5,6,7-triazadibenzo[f,h]naphtho[3,2,1-cd]azulene (PTNA) representing cyclizated five-or seven-membered regioizomeric products of CPDPPQ, respectively. The spectra has been recorded in solvents of different polarity and compared with the results of quantum chemical calculations performed within the semiempirical method PM3. Cyclization of CPDPPQ into DPIPQ or PTNA is accompanied by a significant red shift of the first optical absorption and fluorescence bands. While the solvent polarity rises all the dyes exhibit the hypsochromic (blue) shift of the first absorption band and the bathochromic (red) shift of the fluorescence band. These trends have been reproduced within the semiempirical calculations and explained by nearly antiparallel orientation of the dipole moments in ground and excited states.

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A General Synthesis of Disubstituted Rubicenes

Abstract: The synthesis of novel disubstituted rubicenes 1a–k is described. Starting from 1,5‐dichloroanthraquinone and aryllithium reagents 3, the diol adducts 4 are reduced and the resulting diarylanthracenes 5 are cyclized to afford the title compounds in fair to good overall yield.

Cited by 32 publications

References 11 publications

Pentagon‐Embedded Cycloarylenes with Cylindrical Shapes

Pentagon‐Embedded Cycloarylenes with Cylindrical Shapes

Synthesis of Crown Ethers Containing a Rubicene Moiety

From pirazoloquinolines to annulated analogues of azafluoranthene and azulene dyes: UV-VIS spectroscopy and quantum chemical study

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