The synthesis of dithienobenzoquinones by an intramolecular benzoin condensation: (Short Communication)

Wynberg, Hans; Sinnige, H. J. M.

doi:10.1002/recl.19690881011

Cited by 17 publications

(8 citation statements)

References 5 publications

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“…It is obtained in three steps from commercially available starting materials. The synthesis of 3 has previously been reported by benzoin condensation of the corresponding bithiophene derivative [ 18 ].…”

Section: Resultsmentioning

confidence: 99%

Syntheses and properties of thienyl-substituted dithienophenazines

Meyer¹,

Sigmund²,

Luppertz³

et al. 2010

Beilstein J. Org. Chem.

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SummaryA series of dithienophenazines with different lengths of the oligomeric thiophene units (quaterthiophenes and sexithiophenes) was synthesized. The thiophene and phenazine units act as electron donors and acceptors, respectively, resulting in characteristic absorption spectra. The optical spectra were calculated using time-dependent density functional theory at the B3LYP/TZVP level and verify the experimental data. Adsorption of the dithienophenazines on highly ordered pyrolytic graphite (HOPG) was investigated by scanning tunneling microscopy, showing that one of the compounds forms highly organized self-assembled monolayers.

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Section: Resultsmentioning

confidence: 99%

Syntheses and properties of thienyl-substituted dithienophenazines

Meyer¹,

Sigmund²,

Luppertz³

et al. 2010

Beilstein J. Org. Chem.

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“…Thus, following Jayasuria and Kagan, the bromothiophene was combined with its Grignard reagent in the presence of Ni(dppp)Cl 2 , giving 3,3‘-bithienyl, 5 . Although this bithienyl had previously been transformed into benzo[1,2- b :4,3- b ‘]dithiophene-4,5-dione ( 6 ), an alternative way to effect the transformation was considered, that is a Friedel−Crafts acylation with oxalyl chloride. We thought this procedure could be beneficial because it requires only one step, whereas the previous one requires three−bromination,18a conversion of the resulting 2,2‘-dibromo-3,3‘-bithienyl into the corresponding dialdehyde ( n -butyllithium and then DMF),18b and condensation and oxidation through reflux with ethanolic sodium cyanide in air 18b and in the last step gives a yield of only 50%.…”

Section: Resultsmentioning

confidence: 99%

“…Although this bithienyl had previously been transformed into benzo[1,2- b :4,3- b ‘]dithiophene-4,5-dione ( 6 ), an alternative way to effect the transformation was considered, that is a Friedel−Crafts acylation with oxalyl chloride. We thought this procedure could be beneficial because it requires only one step, whereas the previous one requires three−bromination,18a conversion of the resulting 2,2‘-dibromo-3,3‘-bithienyl into the corresponding dialdehyde ( n -butyllithium and then DMF),18b and condensation and oxidation through reflux with ethanolic sodium cyanide in air 18b and in the last step gives a yield of only 50%. The precedents for installing the diketone bridge in one step include preparations of a number of substituted benzils, a phenanthrene-9,10-dione, and dixobenzo[1,2- b :4,3- b ‘]dipyrroles from aromatic compounds, oxalyl chloride, and aluminum chloride.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Properties of an Aggregating Heterocyclic Helicene

et al. 2001

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Heterohelicene 10 is synthesized in six steps from 3,3'-bithienyl. Because the number of steps is small, because the yield is 95% in the last (the reaction of a bis-enol ether with 1,4-benzoquinone-a six-step one pot procedure that constructs the helicene skeleton), and because chromatography is not required to purify any of the products in the synthesis, significant amounts are easily prepared. To convert 10 into enantiopure 3, a helicenebisquinone surrounded by four dodecyloxy groups, requires only a precedented three-step sequence. Enantiopure helicene 3, either without solvent or in dodecane (but not in chloroform) aggregates into columnar structures whose optical properties differ markedly from those of the monomer but resemble those shown previously only by aggregates of 1. Evidence of aggregation in the pure material includes optical microscopic observation of long fibrous structures and X-ray diffraction and combined transmission electron microscopic and electron diffraction analyses showing the molecules within the fibers to be organized in columnar arrays. The circular dichroism spectra, specific rotations, and fluorescent emission spectra of the aggregated structures are all distinctive, and, as reported elsewhere, the second harmonic response is very large. The linear polarizations of the monomers' and aggregates' fluorescent emissions differ greatly. The circular polarization of the aggregates' fluorescent emission, after excitation by unpolarized light, is large.

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“…14 These tricyclic structures were shown to have large electron affinities, 14 which could potentially give rise to semiconductors that could be fabricated into OFETs with air-stable operation. While electron-transport materials with a monocarbonyl-bridged dithiophene 3,4 and dithiazole 5 cores have been developed, there are only a few reports describing the preparation of materials with benzo[1,2-b:6,5-b 0 ]dithiophene-4,5dione, 7,[15][16][17][18][19][20] and the charge-carrier transport properties of this class of fused dithiophenes (and analogous dithiazoles) were not reported.…”

Section: Introductionmentioning

confidence: 99%