BODIPY–Hexaphyrin Hybrids

Shin, Ji‐Young; Tanaka, Takayuki; Osuka, Atsuhiro; Miao, Qing; Dolphin, David

doi:10.1002/chem.200902407

Cited by 13 publications

(14 citation statements)

References 32 publications

(7 reference statements)

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“…These spectral features of [28]‐hybrids 1 – 3 and [26]‐hybrids 4 – 6 clearly elucidated the aromatic nature of the [28]‐ and [26]hexaphyrin cores in these hybrids, which indicate that [28]‐hybrids 1 – 3 take Möbius aromatic conformation whereas [26]‐hybrids 4 – 6 have Hückel aromatic structure as demonstrated in the literatures 14. 25…”

Section: Resultssupporting

confidence: 64%

“…We synthesized three sets of [28]‐ and [26]‐hybrids, 1 and 4 , 2 and 5 , and 3 and 6 , in which hexaphyrins and bodipys were connected by three different bridging groups, phenylene, biphenylene, and terphenylene, respectively 24. The bodipy precursor of hybrids 1 and 4 , meso ‐(4‐formylphenyl)bodipy, was prepared according to the synthetic method previously reported 25. Similarly, meso ‐(4‐formylbiphenyl)bodipy, precursor of hybrids 2 and 5 , was prepared using 4′‐formyl‐4‐biphenylcarbonitrile.…”

Section: Resultsmentioning

confidence: 99%

“…The hexaphyrin cores were constructed according to the reported procedure 25. BF 3 ⋅ OEt 2 ‐catalyzed condensation of tripyrrane and formyl‐bodipys at low temperature under anaerobic conditions and subsequent oxidation with DDQ (2.0 equiv) successfully provided [28]‐hybrids 1 – 3 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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Photodynamics of [26]‐ and [28]Hexaphyrin–Bodipy Hybrids

Shin

Kim

Lim

et al. 2014

Chemistry A European J

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A set of hybrids having gradual variation in distances between hexaphyrin and bodipy moieties, given by uses of phenylene, biphenylene, and triphenyelene bridges was prepared. Efficient PET processes from bodipy (donor) to [26]- or [28]hexaphyrin (acceptor) were successfully observed, where the PET speed was controlled by intramolecular distances between the donor and the acceptor. UV irradiation at 515 nm raised a band corresponding to the bodipy absorption. As the time delayed, the bodipy bands decreased and new absorption bands at 615 and 580 nm corresponding to respective absorption bands of [28]- and [26]-hybrids gradually appeared. Whereas the femtosecond transient absorption spectra of [28]/[26]-hybrids having terphenylene bridges completely showed energy transfers from bodipy to hexaphyrin, irradiation of the hybrids using 615 and 580 nm pulses did not induce opposite ways of the PET process. On the basis of enlarged center-to-center-distances of [26]-hybrids than those of [28]-hybrids, the set of [26]-hybrids resulted in slow decay/rise processes. PET parameters obtained with the experiments were fairly consistent with the PET parameters calculated.

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Section: Resultssupporting

confidence: 64%

Section: Resultsmentioning

confidence: 99%

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Photodynamics of [26]‐ and [28]Hexaphyrin–Bodipy Hybrids

Shin

Kim

Lim

et al. 2014

Chemistry A European J

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“…[40a] Hexaphyrins involving different substituents are rare. [18c, 42,43] The synthetic scope of [26]hexaphyrin was at first limited to reactions of pyrrole with a few fluorinated aromatic aldehydes. [44] In 2003, Osuka and coworkers published a synthesis starting from PFP-dipyrrane and various aldehydes, involving mostly alkyl-and alkoxy-substituted benzaldehydes.…”

Section: Full Papermentioning

confidence: 99%

“…For this purpose the aminosubstituted dipyrrane 2e and the alkoxy-substituted dipyrranes 10b and 15 were selected which were synthesized according to the literature. [41] Following the method by Osuka et al [43] BF 3 ·OEt 2 was used as the catalyst. With the two alkoxysubstituted dipyrranes 10b and 15 only the formation of the purple [26]hexaphyrins 16a and 16b was observed (Scheme 4).…”

Section: Full Papermentioning

confidence: 99%

Nucleophilic Aromatic Substitution on Pentafluorophenyl‐Substituted Dipyrranes and Tetrapyrroles as a Route to Multifunctionalized Chromophores for Potential Application in Photodynamic Therapy

Gutsche

Ortwerth

Gräfe

et al. 2016

Chemistry A European J

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Abstract:The application of porphyrinoids in biomedical fields like photodynamic therapy (PDT) requires the introduction of functional groups to adjust their solubility in the biological environment and to allow a coupling to other active moieties or carrier systems. A valuable motif in this regard is the pentafluorophenyl (PFP)-substituent, as the PFP-group easily undergoes a regiospecific nucleophilic replacement (S N Ar) of the para-fluorine atom by a number of nucleophiles. Here, it is shown that -alternatively to an amino-substitution on the final porphyrinoid or BODIPY -the precursor 5-(PFP)-dipyrrane can be modified with amines (or alcohols). These dipyrranes were transformed into amino-substituted BODIPYs. Condensation of these dipyrranes with aldehydes gives access to trans-A 2 B 2 -porphyrins and -A 2 B-corroles. Using pentafluorobenzaldehyde another para-fluorine atom can be introduced enabling the synthesis of multifunctionalized tetrapyrroles. Furthermore, alkoxy-and amino-substituted dipyrranes were applied to the synthesis of A 3 B 3 -hexaphyrins. With this approach polar porphyrins can be prepared, which exhibit in vitro PDT activity against several tumor cell lines.

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Expandierte Porphyrine: überraschende Strukturen, elektronische Eigenschaften und Reaktivitäten

2011

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Die Chemie von expandierten Porphyrinen, den höheren Homologen der Porphyrine, wurde im Laufe der letzten drei Jahrzehnte ausgiebig untersucht. Expandierte Porphyrine weisen Strukturen, elektronische Eigenschaften, Reaktivitäten und ein Koordinationsverhalten auf, die sich gänzlich von denen der Porphyrine unterscheiden. Im Laufe dieser Untersuchungen wurde immer deutlicher, dass expandierte Porphyrine im Hinblick auf ihre Aromatizität und die Koordination an mehrere Metallionen oder als funktionelle Farbstoffe, nichtlinear‐optische Materialien, Ionenrezeptoren, stabile organische Radikale und vieles mehr äußerst attraktiv sind. Kontinuierlich tauchen expandierte Porphyrine mit überraschenden neuen Strukturen und Eigenschaften auf. Letzteres wird durch die einfache Synthese Möbius‐aromatischer und sogar antiaromatischer Systeme mit verdrillten Molekülstrukturen besonders deutlich. Hier werden Fortschritte auf dem Gebiet der expandierten Porphyrine seit dem Erscheinen des Aufsatzes von Sessler und Seidel im Jahr 2003 dargelegt.

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BODIPY–Hexaphyrin Hybrids

Cited by 13 publications

References 32 publications

Photodynamics of [26]‐ and [28]Hexaphyrin–Bodipy Hybrids

Photodynamics of [26]‐ and [28]Hexaphyrin–Bodipy Hybrids

Nucleophilic Aromatic Substitution on Pentafluorophenyl‐Substituted Dipyrranes and Tetrapyrroles as a Route to Multifunctionalized Chromophores for Potential Application in Photodynamic Therapy

Expandierte Porphyrine: überraschende Strukturen, elektronische Eigenschaften und Reaktivitäten

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