Mechanism of transformation of diphenylcarbene into an oligomer of piperylene

Vorotnikov, A. P.; Davydov, E. Ya.; Toptygin, D.Ya.

doi:10.1007/bf00954336

Cited by 1 publication

(3 citation statements)

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“…Nevertheless, the zinc complex of 9 has been reported to show a Soret band at 439 nm and strong long-wavelength band at 701 nm (Table 2) [57,58]. The low solubility of this system can be improved by the introduction of meso-aryl substituents [59][60][61]. In a study by Kobayashi et al the zinc complex tetraaryltetranaphthoporphyrin (10) was reported to give multiple, rather weak Soret bands (429-461 nm) but more significantly a strong band was observed at 698 nm ( Table 2) [59].…”

Section: Naphtho[23-b]porphyrins and Related Linearly Annealed Naphtmentioning

confidence: 99%

“…The data indicate that linearly annealed aromatic subunits have a relatively small influence on the max values for the Soret bands, although the absorptivities are somewhat diminished, but they show a strong tendency to enhance and red shift the longest wavelength Q band. Unfortunately, at present the synthetic routes to these systems produce complex mixtures [59][60][61]. Nonetheless, the available data shows that the UV-vis spectra become more phthalocyanine-like with strong bands in the far red region of the visible spectrum.…”

Section: Naphtho[23-b]porphyrins and Related Linearly Annealed Naphtmentioning

confidence: 99%

“…Porphyrinoid (58) shows a strong Soret band at 422 nm with a shoulder at 436 nm, while the dication in 2% TFAchloroform affords a stronger Soret band at 429 nm with an inflection at 442 nm (Table 8) [114]. The benzo derivative (59) produced Soret bands at 424 nm (free base) and 442 nm, while values of 432 and 450 nm were recorded for the phenanthrene-fused structure (60) and the acenaphtho porphyrinoid gave absorptions at 436 and 460 nm [113]. Similar trends were manifest for the metal chelates of these oxypyriporphyrins, although the appearance of the spectra for the zinc complexes were quite different from the copper(II) and nickel(II) porphyrinoids (Table 8) [113,114].…”

Section: Do These Trends Hold True For Porphyrin Analogues?mentioning

confidence: 99%

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Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

Lash

2001

J. Porphyrins Phthalocyanines

122

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ABSTRACT:The effects exerted by fused aromatic rings on the UV-vis spectra of porphyrins are surveyed. Modified porphyrin chromophores with fused benzene, 1,2-naphthalene, 9,10-phenanthrene or phenanthroline rings are surprisingly little affected even when a maximum number of ring fusions are incorporated. Linearly annealed naphtho-or anthraporphyrins show large red shifts to the Q bands but the Soret absorptions are weakened and undergo only minor bathochromic shifts. Fluoranthoporphyrins give multiple bands in the Soret region, but the Q band region is virtually unaffected by this tetracyclic ring system. On the other hand, metal chelates of fluoranthoporphyrins show surprisingly strong bands near 600 nm. Benzothiadiazole rings split and weaken the Soret band, but the Q bands region is unexceptional. However, metal coordination again produces relatively intense bands near 600 nm. The most significant results were obtained for porphyrins with fused acenaphthylene rings. Monoacenaphthoporphyrins (41) have three Soret bands at 387, 431 and 454 nm, and the longest wavelength Q band is shifted to 658 nm. opp-Diacenaphthoporphyrin (43) further shifts these bands with two Soret absorbances at 443 and 470 nm, and an additional strong peak is observed at 692 nm. The metal complexes of these systems also show strong bands between 602 and 656 nm. Still larger effects are produced by tetraacenaphthoporphyrin (47), the dication for which in trifluoroacetic acid (TFA)-chloroform has a Soret absorption at 528 nm. Tetraaryltetraacenaphthoporphyrins (48) are even more red shifted, showing Soret bands between 556 and 570 nm for the free bases and 565 to 588 nm for the related dications. The lead(II) chelate for tetraphenylporphyrin (48a) shows an additional 'hyper' spectral shift that brings the Soret band to 604 nm, and this effect can also be achieved by introducing four meso-phenylethynyl substituents onto the tetraacenaphthoporphyrin nucleus (49). In addition, by combining these two factors for the lead(II) chelate of 49, a record-breaking value for the Soret band of 642 nm can be achieved. Spectral shifts due to ring annelation in porphyrin analogues are also discussed, including those for oxybenziporphyrins, oxypyriporphyrins, carbaporphyrins and sapphyrins.

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Section: Naphtho[23-b]porphyrins and Related Linearly Annealed Naphtmentioning

confidence: 99%

Section: Naphtho[23-b]porphyrins and Related Linearly Annealed Naphtmentioning

confidence: 99%

Section: Do These Trends Hold True For Porphyrin Analogues?mentioning

confidence: 99%

See 1 more Smart Citation

Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

Lash

2001

J. Porphyrins Phthalocyanines

122

View full text Add to dashboard Cite

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Mechanism of transformation of diphenylcarbene into an oligomer of piperylene

Cited by 1 publication

References 2 publications

Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

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