Hexaphyrin Fused to Two Anthracenes

Naoda, Koji; Mori, Haruo; Aratani, Naoki; Lee, Bu-Sung; Kim, Dongho; Osuka, Atsuhiro

doi:10.1002/anie.201204446

Cited by 39 publications

(20 citation statements)

References 53 publications

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“…Some metal complexes and fused congeners of hexaphyrins are very appealing, since they give rise to absorption profiles that are shifted deeper into the red region than those of the corresponding free‐base analogues (hexaphyrins 4 – 7 in Figure 1). 2–4 Metalation of hexaphyrins often proceeds with large conformational changes or via metal‐triggered CH bond activation, which usually requires relatively harsh conditions 5. Fused hexaphyrin skeletons ( 6 and 7 ) give redshifted absorption bands, but are prepared through tedious multistep syntheses 3.…”

Section: Methodsmentioning

confidence: 99%

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Bismetal Complexes of 5,20‐Bis(5‐formyl‐2‐pyrrolyl)‐[26]hexaphyrin(1.1.1.1.1.1) Exhibiting Strong Near‐Infrared Region Absorptions

Mori

Osuka

2015

Chemistry A European J

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[26]Hexaphyrin(1.1.1.1.1.1) bearing two 5-formyl-2-pyrrolyl groups at the 5- and 20-positions was prepared by cross-condensation of 5,10-bis(pentafluorophenyl)-substituted tripyrrane with 2,5-diformylpyrrole as an effective binuclear metal-coordinating ligand, owing to the two hemiporphyrin-like NNNN pockets. In fact, metalation of this hexaphyrin with Zn(II) , Cu(II) , and Pd(II) salts proceed smoothly at room temperature to give the corresponding bismetal complexes that displayed remarkably redshifted absorption spectra reaching deep into near infrared region. These redshifted absorption bands are ascribed, through electrochemical investigations and DFT calculations, to two structural motifs: the N-metalopyrrole substructure that elevates the HOMO level due to the electron-donating property and the two coordinated metal ions that serve as Lewis acids to lower the LUMO level.

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Section: Methodsmentioning

confidence: 99%

“…Fused hexaphyrin skeletons ( 6 and 7 ) give redshifted absorption bands, but are prepared through tedious multistep syntheses 3. 4 Therefore, hexaphyrins that allow smoother metalation under milder conditions to provide metal complexes exhibiting redshifted absorption bands in the near‐infrared region (NIR) region are highly desirable.…”

Section: Methodsmentioning

confidence: 99%

Bismetal Complexes of 5,20‐Bis(5‐formyl‐2‐pyrrolyl)‐[26]hexaphyrin(1.1.1.1.1.1) Exhibiting Strong Near‐Infrared Region Absorptions

Mori

Osuka

2015

Chemistry A European J

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“…185 Such an aromaticity-switching behaviour in triply linked porphyrin arrays is quite rare and so further elaborations of this fused expanded porphyrin motif will be promising for the creation of novel functional materials. 186 Scheme 59 Synthesis of 3,3 0 -linked corrole oligomers.…”

Section: Porphyrin-hexaphyrin Hybrid Arraysmentioning

confidence: 99%

Conjugated porphyrin arrays: synthesis, properties and applications for functional materials

2015

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Conjugated porphyrin arrays that possess delocalised electronic networks have, for the most part, been assembled by using alkene or alkyne type bridging units or by directly connecting individual porphyrin chromophores with multiple bonds to form fused porphyrin arrays. Throughout the last two decades, such conjugated porphyrin arrays have been actively explored due to their attractive electronic, optical and electrochemical properties. This review aims to cover the multitude of synthetic methodologies that have been developed for the construction of conjugated porphyrin arrays as well as to summarise their structure-property relationships and use in various applications such as near infrared (NIR) dyes, nonlinear optical materials and electron-conducting molecular wires.

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“…19). 165 The oxidative fusion reaction of bis(mesityloxy)anthracene-bearing hexaphyrin bis-Au(III) complex 162 proceeded successfully upon treatment with DDQ and Sc(OTf) 3 . The single-crystal X-ray analysis displayed an elongated, rectangular, almost planar structure of 163 (Fig.…”

Section: Fused Porphyrin Oligomersmentioning

confidence: 99%

Fused porphyrinoids as promising near-infrared absorbing dyes

2013

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Various aromatic segments have been fused onto the porphyrin periphery to create porphyrinoids that have expanded p-conjugated networks and thus exhibit red-shifted absorption spectra. Fused coplanar porphyrin oligomers, represented by meso-meso, b-b, b-b triply linked porphyrin arrays (porphyrin tapes), are endued with more red-shifted absorption spectra and better nonlinear optical properties.These fused porphyrinoids have emerged as promising near-infrared (NIR) absorbing dyes, pointing to future applications such as conducting wire, NIR emitter, photovoltaics, and nonlinear optical materials.Developments of the fused porphyrinoid chemistry are reviewed in this feature article with focus on the synthesis, the relationships between their absorption spectra and molecular structures, and the applications in materials science.

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Hexaphyrin Fused to Two Anthracenes

Cited by 39 publications

References 53 publications

Bismetal Complexes of 5,20‐Bis(5‐formyl‐2‐pyrrolyl)‐[26]hexaphyrin(1.1.1.1.1.1) Exhibiting Strong Near‐Infrared Region Absorptions

Bismetal Complexes of 5,20‐Bis(5‐formyl‐2‐pyrrolyl)‐[26]hexaphyrin(1.1.1.1.1.1) Exhibiting Strong Near‐Infrared Region Absorptions

Conjugated porphyrin arrays: synthesis, properties and applications for functional materials

Fused porphyrinoids as promising near-infrared absorbing dyes

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