Palladium-Catalyzed Synthesis of Alkynylated 1,4:5,8:11,14:15,18-Tetrasulfido[20]annulenes

Dahlmann, Uwe; Krieger, Claus; Neidlein, R.

doi:10.1002/(sici)1099-0690(199803)1998:3<525::aid-ejoc525>3.0.co;2-2

Cited by 13 publications

(4 citation statements)

References 20 publications

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“…Neidlein and co-workers 78 obtained the alkynyl-substituted annulenes 97 via Sonogashira coupling 79 using the corresponding tetrabrominated macrocyle (obtained from the brominated bipyrrole 96) as the starting material (Scheme 29). However, there is no report of any successful oxidation to an aromatic species corresponding to the so-far hypothetical dication 95.…”

Section: Porphycene Analogues Containing Furan Thiophene or Imidazole...mentioning

confidence: 99%

Porphycenes: synthesis and derivatives

2008

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Porphycene is an aromatic macrocycle and a constitutional isomer of porphyrin. It and its derivatives display unique physical and optical properties, including strong absorptions in the red region of the UV-vis spectrum. These features have made porphycene and porphycene analogues appealing molecules for use in biomedical applications and in the design of new materials. This critical review provides a concise overview of the most important syntheses of porphycenes, as well as those of various functionalized derivatives and heteroatom containing analogues. (95 references.)

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Section: Porphycene Analogues Containing Furan Thiophene or Imidazole...mentioning

confidence: 99%

Porphycenes: synthesis and derivatives

2008

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“…[34][35] Neilden and coworkers reported bromo functionalized tetrathiaporphycene by a similar synthetic strategy were McMurry coupling of 38 to obtain the tetrabromothiaporphycene macrocycle 39 in 26 % yield (Scheme 11). [36] The tetrabromothiaporphycene 39 was subjected to Sonagashira coupling reaction with ethynes in the presence of Pd-(PhCN) 2 Cl 2 /PPh 3 /CuI in diisopropylamine under reflux conditions to afford tetraethynylthiaporphycene macrocycles 40 (Scheme 11). This particular strategy has the potential to be used for designing dyads or other molecular wires with 20π nonaromatic macrocycles.…”

Section: Heteroatom Modification In the Core Of The Macrocyclementioning

confidence: 99%

Synthesis and Properties of Stable 20π Porphyrinoids

Pushpanandan

Ravikanth

2022

The Chemical Record

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The 20π porphyrinoids are immediate higher homologues of 18π porphyrins and differ from porphyrins in aromaticity which in turn affects the structure, properties and chemical reactivities. Research over the years indicated that the 20π porphyrinoids can be stabilized as non-aromatic/anti-aromatic or Mobius aromatic macrocycles using different strategies such as core-modification of porphyrins, non-metal/metal complexation of porphyrins, peripheral modification of porphyrins and expanded porphyrinoids. The structural properties such as aromaticity of the macrocycle can be controlled by choosing the right synthetic strategy. This review will provide an overview of the development in the chemistry of 20π porphyrinoids giving emphasize on the synthesis, structure and electronic properties of these macrocycles which have huge potential for various applications.

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“…With some exceptions, 38 almost all the analogues prepared are unsubstituted macrocycles. The general synthetic pathway follows the main principles of Vogel's synthesis of porphycenes and is predicated on the McMurry coupling of the proper dialdehydes.…”

Section: Porphycene Heteroanaloguesmentioning

confidence: 99%

Porphycenes and Related Isomers: Synthetic Aspects

Anguera

Sánchez‐García

2016

Chem. Rev.

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Porphyrins, called the pigments of life, have been studied for decades. However, the first constitutional isomer of porphyrin, porphycene, was not synthesized until 1986. This milestone marked the beginning of a new era in the field of porphyrinoids and presented opportunities for the creation of an abundance of new pigments. The unique structural and electronic features of these compounds give rise to interesting physical and optical properties with applications in biomedicine and materials science. This review focuses on the synthetic methodologies available for the preparation of porphycenes (functionalized porphycenes, extended porphycenes, benzoporphycenes, naphthoporphycenes, and heteroanalogues) and the other known isomers, namely, corrphycene, hemiporphycene, and isoporphycene. Although the classical synthetic approaches are discussed, particular emphasis is placed on improvements to the known methodologies and recent advances in the field.

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Palladium-Catalyzed Synthesis of Alkynylated 1,4:5,8:11,14:15,18-Tetrasulfido[20]annulenes

Cited by 13 publications

References 20 publications

Porphycenes: synthesis and derivatives

Porphycenes: synthesis and derivatives

Synthesis and Properties of Stable 20π Porphyrinoids

Porphycenes and Related Isomers: Synthetic Aspects

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