Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction

Kotha, Sambasivarao; Ghosh, Arun K.; Deodhar, K. D.

doi:10.1055/s-2004-815981

Cited by 33 publications

(21 citation statements)

References 30 publications

(32 reference statements)

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“…9,10-Bis(2-thienyl)anthracene (8). 13 A mixture of 9,10dibromoanthracene (9 g, 26.78 mmol), 2-tributylstannylthiophene 7 (18.7 mL, 58.92 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in dry toluene (250 mL) was heated under nitrogen. The reaction mixture was refluxed for 3 days during which time a precipitate formed.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Properties of Hexyl End-Capped Thiophene Oligomers Containing Anthracene Moiety in the Center

Choi¹,

Cho²,

Jin³

et al. 2007

Bulletin of the Korean Chemical Society

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A series of new organic semiconductors hexyl end-capped thiophene-anthracene oligomers containing the anthracene moiety in the center of the oligomers are synthesized. The target oligomers have been obtained by Stille coupling reactions as key step reactions. The synthesized thiophene-anthracene oligomers were characterized by 1 H-NMR, 13 C-NMR and high-resolution mass spectroscopy, respectively. All of the oligomers are soluble in chlorinated solvents. Their optical, thermal and electrochemical properties were measured. The hexyl end-capped oligomers and their unsubstituted oligomers exhibit the same absorption behavior in dilute toluene solution. Hexyl end-capped bis-terthienylanthracene oligomer is observed to show liquid crystalline mesophase at 166 o C in heating process. The thermal analyses as well as the electrochemical measurement data indicate that the designed materials show better thermal and oxidation stability than the corresponding oligothiophenes without anthracene core. Fluorescence lifetimes and fluorescence quantum yields of the thiophene-anthracene oligomers are measured to be 10-14 ps and 3.4-9.9 × 10 −3 which are much shorter and lower than those of oligothiophenes respectively.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Properties of Hexyl End-Capped Thiophene Oligomers Containing Anthracene Moiety in the Center

Choi¹,

Cho²,

Jin³

et al. 2007

Bulletin of the Korean Chemical Society

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“…We found that it is possible to couple the dibromide 19 with various boronic acids in the presence of Pd(PPh 3 ) 4 catalyst (Scheme 6), [19,20] with 42-99 % yields of the coupling products 20a-l typically being obtained. It may be relevant to mention that the substrate 20d has also been prepared by a four-step sequence involving the Grignard coupling reaction as a key step.…”

Section: Synthesis Of 910-diarylanthracene Derivatives By Double Sm mentioning

confidence: 99%

“…[21] Furthermore, the aldehyde functionality present in 20d can be used for additional synthetic elaboration. Scheme 6. To prepare unsymmetrical 9,10-diarylanthracene derivatives, [20] compound 19 was treated with 1.5 equivalents of thien-2-ylboronic acid under the same reaction conditions to generate 9-bromo-10-(thien-2-yl)anthracene (22) in 79% isolated yield (Figure 3). Selective SM reactions with other heteroarylboronic acids were attempted next, and typically 61-90 % yields of the monocoupled products 21-25 were obtained.…”

Section: Synthesis Of 910-diarylanthracene Derivatives By Double Sm mentioning

confidence: 99%

Expanding the Diversity of Polycyclic Aromatics Through a Suzuki–Miyaura Cross‐Coupling Strategy

Kotha

Lahiri

2007

Eur J Org Chem

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In recent years, Pd‐catalyzed Suzuki–Miyaura (SM) cross‐coupling reactions have revolutionized approaches to carbon–carbon bond formation. We have studied the application of SM coupling with several (ca. 16) complex molecular structures of particular relevance to scientists working at the interfaces of chemistry, biology, and materials sciences. In this regard, various structurally or biologically important polycyclic molecules (e.g., benzocrowns, C3‐symmetric molecules, 9,10‐disubstituted anthracenes, and sulfones) and unusual amino acid derivatives have been modified by this reaction, while it has also been shown that allylation of aromatics through the use of a commercially available boronic acid ester by SM coupling under CsF/Pd0 conditions is feasible. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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“…[30,36] p-(10-Bromoanthryl)-benzonitrile could then be used to synthesise the triazine ligand by employing the same procedure as used for L1. [27,31] The 1 H NMR spectra for 3 d and 3 e in CD 3 CN at 400 MHz are shown in Figure 1.…”

Section: Rumentioning

confidence: 99%

Tuning the Excited‐State Energy of the Organic Chromophore in Bichromophoric Systems Based on the Ru^II Complexes of Tridentate Ligands

Medlycott

Hanan

Loiseau

et al. 2007

Chemistry A European J

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A series of new heteroleptic and homoleptic Ru(II) complexes containing variously substituted bis(pyridyl)triazine ligands has been prepared and their absorption spectra, redox behaviour and luminescence properties (both in fluid solution at room temperature and in a rigid matrix at 77 K) have been investigated. For some compounds, X-ray structures have also been determined. The new bis(pyridyl)triazines incorporate additional chromophores, such as biphenyl, phenanthrene, anthracene and bromoanthracene derivatives, so the Ru(II) species can be considered as multichromophoric species. The absorption spectra and redox properties of all the metal complexes have been assigned to features belonging to specific subunits, thus suggesting that these species can be regarded as multicomponent, supramolecular assemblies from an electronic coupling point of view. Whereas most of the complexes exhibit luminescence properties that can be attributed to metal-to-ligand charge-transfer (MLCT) states involving the metal-based subunit(s), the species containing the anthryl and, even more, the brominated anthryl chromophores exhibit complicated luminescence behaviour. For example, 2 d (the anthryl-containing heteroleptic metal compound) exhibits MLCT emission at room temperature and emission from the anthracene triplet at 77 K; 2 e (the bromo-substituted anthryl-containing heteroleptic metal compound) exhibits anthryl-based emission at 77 K and MLCT emission at room temperature, but with a prolonged lifetime, thus suggesting equilibration between two triplet states that belong to different chromophores. The equilibration regime between MLCT and aromatic hydrocarbon triplet states is therefore reached by suitable substitution on the organic chromophore.

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Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction

Cited by 33 publications

References 30 publications

Synthesis and Properties of Hexyl End-Capped Thiophene Oligomers Containing Anthracene Moiety in the Center

Synthesis and Properties of Hexyl End-Capped Thiophene Oligomers Containing Anthracene Moiety in the Center

Expanding the Diversity of Polycyclic Aromatics Through a Suzuki–Miyaura Cross‐Coupling Strategy

Tuning the Excited‐State Energy of the Organic Chromophore in Bichromophoric Systems Based on the Ru^II Complexes of Tridentate Ligands

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Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction

Cited by 33 publications

References 30 publications

Synthesis and Properties of Hexyl End-Capped Thiophene Oligomers Containing Anthracene Moiety in the Center

Synthesis and Properties of Hexyl End-Capped Thiophene Oligomers Containing Anthracene Moiety in the Center

Expanding the Diversity of Polycyclic Aromatics Through a Suzuki–Miyaura Cross‐Coupling Strategy

Tuning the Excited‐State Energy of the Organic Chromophore in Bichromophoric Systems Based on the RuII Complexes of Tridentate Ligands

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Tuning the Excited‐State Energy of the Organic Chromophore in Bichromophoric Systems Based on the Ru^II Complexes of Tridentate Ligands