One-step synthesis of dialkynyl-1,2-diones and their conversion to fused pyrazines bearing enediyne units

Faust, Rüdiger; Weber, Christian; Fiandanese, Vito; Marchese, Giuseppe; Punzi, Angela

doi:10.1016/s0040-4020(97)01007-7

Cited by 66 publications

(58 citation statements)

References 40 publications

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“…Presumably, the copper acetylide was not formed in the reaction of iPr 3 SiÀCCH with CuOAc. However, when the copper acetylide was generated by transmetalation of iPr 3 SiÀCCÀLi with CuBr [23] and subsequently reacted with TCNE, CEE 8 was isolated in a yield of 33 % (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Donor‐Substituted Cyanoethynylethenes: π‐Conjugation and Band‐Gap Tuning in Strong Charge‐Transfer Chromophores

Moonen

Pomerantz

Gist

et al. 2005

Chemistry A European J

107

114

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An extensive series of silyl-protected cyanoethynylethenes (CEEs) and N,N-dimethylanilino donor-substituted CEEs have been synthesized. More extended chromophores were constructed by selective silyl deprotection and subsequent oxidative acetylenic coupling. The strong electron-accepting nature of the CEEs was revealed by a combination of 13C NMR spectroscopic and electrochemistry measurements. Donor-substituted CEEs display strong intramolecular charge-transfer (CT) character, resulting in intense, bathochromically shifted CT bands in the UV/Vis spectrum. Their structural diversity establishes them as suitable models for the study of pi-conjugation and band gap tuning in strong charge-transfer chromophores. The extent of pi-conjugation in the donor-substituted CEEs was investigated by a combination of ground-state techniques, such as X-ray crystallography, electrochemistry, B3 LYP calculations, and NMR spectroscopy. The comparison of these ground-state results with the features observed in the UV/Vis spectra reveals that-contrary to expectations-more extensive pi-conjugation can lead to larger band gaps in molecules with strong donor and acceptor moieties.

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Section: Introductionmentioning

confidence: 99%

Donor‐Substituted Cyanoethynylethenes: π‐Conjugation and Band‐Gap Tuning in Strong Charge‐Transfer Chromophores

Moonen

Pomerantz

Gist

et al. 2005

Chemistry A European J

107

114

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“…[25,26] The building blocks common to all of these chromophores, the readily available dialkynyl 1,2-diones 1 [27] ( Figure 1), ensure that the macrocycles benefit from extended π-systems and, in comparison to non-alkynylated congeners, from the associated batho-and hyperchromically shifted absorption profiles. In addition, acetylene substitution provides a convenient synthetic handle with which to modulate the solubility properties of the chromophores by varying the terminal alkyne substituents.…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of Arylalkyne‐Substituted Tetrapyrazinoporphyrazines and an Evaluation of Their Potential as Photosensitisers for Photodynamic Therapy

et al. 2004

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New aryl-terminated octaalkynyl tetrapyrazinoporphyrazines were prepared in three steps starting from functionalised bisarylalkynyl 1,2-diones. While the tert-butylphenyl substituents were shown to aid solubility in organic solvents and to reduce chromophore aggregation efficiently, more hydrophilic tetrapyrazinoporphyrazines were obtained through the use of polyethylene glycol-substituted (PEGsubstituted) phenyl groups. The absorption profiles and the singlet oxygen quantum yields of the acetylenic tetrapyrazinoporphyrazines were determined with a view to assess their suitability for PDT applications. In all cases the presence of the terminal aryl moieties resulted in noticeable bathochromic and hyperchromic shifts of the lowest-energy ab-

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“…[23] The starting material for the synthesis of DVT was 2-(4-azidophenyl)-4,5-diphenyl-1H-imidazole (API), which was prepared from its amine derivate via the Sandmeyer reaction. [26] The substitution of aromatic amino group was carried out via preparation of its diazonium salt and subsequent nucleophilic displacement with sodium azide (see SI). The API was then coupled to but-3-yn-1-ol in the presence of Cu(I) to give 1,4-disubstituted-triazole.…”

Section: Synthesis Of Monomermentioning

confidence: 99%

Synthesis and RAFT polymerization of a novel vinyl monomer containing both triarylimidazole and triazole moieties

Huang

Peng

Chen

et al. 2014

Designed Monomers and Polymers

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A novel monomer consisting of a 4-vinyl-1,2,3-triazole unit directly linked to a triphenylimidazole unit, 1-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl)-4-vinyl-1H-1,2,3-triazole (DVT), has been successfully synthesized using click chemistry followed by elimination reaction. Subsequently, poly(DVT) was prepared by the reversible addition-fragmentation chain transfer (RAFT) polymerization of DVT in dimethyl sulfoxide using S-dodecyl-S′-(α,α′-dimethyl-α″-acetic acid)-trithiocarbonate (DMP) as the RAFT agent and 2,2′-azobis(isobutyronitrile) (AIBN) as the initiator. Kinetic studies demonstrated that the polymerization process of DVT followed pseudo-first-order kinetics with respect to the monomer concentrations. The molecular weight of the resulting polymer increased linearly with monomer conversion, while a low polydispersity was maintained throughout. In addition, the poly(DVT) showed the characteristic of temperature-dependent absorbance in the near-ultraviolet (UV) spectral region, of which a linear dependence of UV absorbance on temperature was confirmed for the polymer both in solution and in solid states.

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One-step synthesis of dialkynyl-1,2-diones and their conversion to fused pyrazines bearing enediyne units

Cited by 66 publications

References 40 publications

Donor‐Substituted Cyanoethynylethenes: π‐Conjugation and Band‐Gap Tuning in Strong Charge‐Transfer Chromophores

Donor‐Substituted Cyanoethynylethenes: π‐Conjugation and Band‐Gap Tuning in Strong Charge‐Transfer Chromophores

The Synthesis of Arylalkyne‐Substituted Tetrapyrazinoporphyrazines and an Evaluation of Their Potential as Photosensitisers for Photodynamic Therapy

Synthesis and RAFT polymerization of a novel vinyl monomer containing both triarylimidazole and triazole moieties

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