Selenobenzophenones and Diazoalkanes: Isolation of Tetraarylethylenes by the Reaction of Benzophenone Hydrazones with Diselenium Dibromide

Okuma, Kentaro; Kojima, Kazuki; Oyama, Kosuke; Kubo, Kento; Shioji, Kosei

doi:10.1002/ejoc.200300510

Cited by 12 publications

(5 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore, they have shown that the reaction of benzophenone hydrazone with diselenium dibromide using triethylamine at room temperature gives TPE in 81% yield. 26 Tezuka et al reported copper-catalyzed selfcoupling of dichlorodiphenylmethane ( 6) in DMSO at room temperature to obtain 1 in 97% yield. 27 Another approach to synthesize TPE in 75% yield is by the double arylation reaction of diphenylacetylene (7) using phenylboronic acid (8) and iodobenzene (9) in the presence of palladium(II) acetate (Pd(OAc) 2 ) in DMSO.…”

Section: General Synthesesmentioning

confidence: 99%

“…In another report, Otura et al described the reaction of selenobenzophenone ( 4 ) with diphenyldiazomethane ( 5 ) in DCM at −78 °C to afford a 76% yield of 1 . Furthermore, they have shown that the reaction of benzophenone hydrazone with diselenium dibromide using triethylamine at room temperature gives TPE in 81% yield . Tezuka et al reported copper-catalyzed self-coupling of dichlorodiphenylmethane ( 6 ) in DMSO at room temperature to obtain 1 in 97% yield .…”

Section: General Synthesesmentioning

confidence: 99%

See 1 more Smart Citation

Tetraphenylethylene-Based AIE-Active Probes for Sensing Applications

La¹,

Bhosale

Jones³

2017

ACS Appl. Mater. Interfaces

449

225

View full text Add to dashboard Cite

This Review provides a comprehensive analysis of recent development in the field of aggregation-induced emission (AIE)-active tetraphenylethylene (TPE) luminophores and their applications in biomolecular science. It begins with a discussion of the diverse range of structural motifs that have found particular applications in sensing, and demonstrates that TPE structures and their derivatives have been used for a diverse range of analytes such as such as H, anions, cations, heavy metals, organic volatiles, and toxic gases. Advances are discussed in depth where TPE is utilized as a mechanoluminescent material in bioinspired receptor units with specificity for analytes for such as glucose or RNA. The rapid advances in sensor research make this summary of recent developments in AIE-active TPE luminophores timely, in order to disseminate the advantages of these materials for sensing of analytes in solution, as well as the importance of solid and aggregated states in controlling sensing behavior.

show abstract

Section: General Synthesesmentioning

confidence: 99%

Section: General Synthesesmentioning

confidence: 99%

Tetraphenylethylene-Based AIE-Active Probes for Sensing Applications

La¹,

Bhosale

Jones³

2017

ACS Appl. Mater. Interfaces

449

225

View full text Add to dashboard Cite

show abstract

“…Furthermore, the procedures that are generally utilized for the preparation of unsymmetrical tetraarylethylenes either require the multistep synthesis of precursors or suffer from low yields. The reactions of resonance stabilized selenoketones with diaryldiazomethane, benzophenone hydrazones with diselenium dibromide, the Pd-catalyzed three-component coupling of aryl iodides/internal alkynes/arylboronic acids, and the Pd-catalyzed sequential assembly using a vinyl 2-pyrimidyl sulfide core give either a mixture of products or are not amenable for large-scale syntheses.…”

Section: Introductionmentioning

confidence: 99%

Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads

et al. 2007

View full text Add to dashboard Cite

We have demonstrated that reactions of diphenylmethyllithium with a variety of substituted benzophenones produces corresponding tertiary alcohols that are easily dehydrated, without any need for purification, to produce various unsymmetrical and symmetrical tetraarylethylenes in excellent yields. The simplicity of the method allows for the preparation of a variety of ethylenic derivatives in multigram (10−50 g) quantities with great ease. The methodology was successfully employed for the preparation of various triphenylethylene (TPE)based triads (i.e., TPE−spacer−TPE) containing polyphenylene and fluoranyl-based spacers. The ready availability of various substituted tetraarylethylenes allowed us to shed light on the effect of substituents on the oxidation potentials (Eox) of various tetraarylethylenes. Moreover, the electronic coupling among the triphenylethylene moieties in various TPE−spacer−TPE triads was briefly probed by electrochemical and optical methods.

show abstract

“…Among AIE-sulfonates, tetraphenylethylene (TPE) is the most common AIE-active moiety and is generally synthesized by McMurry cross-coupling of suitable benzophenone derivatives. [40][41][42] The incorporation of sulfonate functionality in the TPE moiety is commonly achieved by alkylation of hydroxyl groups of TPE derivative with propane or butane sultone in the presence of a base such as sodium hydroxide, sodium ethoxide or sodium hydride resulting in the formation of TPE derivative containing diagonally placed sulfonate functionality attached via a short alkyl chain (2-4) (Scheme 1a). As per the need of the number of À SO 3…”

Section: General Synthesismentioning

confidence: 99%

Sulfonate‐Functionalized AIEgens: Strategic Approaches Beyond Water Solubility for Sensing and Imaging Applications

2022

View full text Add to dashboard Cite

The development of water-soluble aggregation-induced emission (AIE)-active "light-up" probes for sensing and imaging purposes has drawn immense research attention in the recent past. One strategy has been to introduce À SO 3 À groups in AIEgens (AIE-sulfonates) to increase their hydrophilic properties, and the ionic nature of the corresponding compounds also paves the way for electrostatic interaction with various analytes, in particular, with several biospecies having positively charged surfaces. A significant number of AIE-sulfonates, many among them having a tetraphenylethylene (TPE) moiety, have been designed and synthesized for the selective detection of a variety of analytes, such as metal ions, small molecules, enzymes, proteins, and bacteria. The strategies for selective detection include, for example, spontaneous complex formation with cations, electrostatic interaction with target-specific units in the biospecies, and strong hydrophobic interactions. In addition, these AIEgens are used in cell imaging and OLED applications. This Review attempts to provide a summary and discuss recent developments in sulfonate-functionalized AIEactive "light-up" probes in sensing and imaging applications with a focus on the role of the sulfonate functionality in the design and sensing processes.

show abstract

Selenobenzophenones and Diazoalkanes: Isolation of Tetraarylethylenes by the Reaction of Benzophenone Hydrazones with Diselenium Dibromide

Cited by 12 publications

References 38 publications

Tetraphenylethylene-Based AIE-Active Probes for Sensing Applications

Tetraphenylethylene-Based AIE-Active Probes for Sensing Applications

Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads

Sulfonate‐Functionalized AIEgens: Strategic Approaches Beyond Water Solubility for Sensing and Imaging Applications

Contact Info

Product

Resources

About