76 Syntheses of Bacteriochlorins and Isobacteriochlorins

Brückner, Christian; Samankumara, Lalith P.; Ogikubo, Junichi

doi:10.1142/9789814335508_0003

Cited by 58 publications

(83 citation statements)

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“…27 However, the metal complexes of bacteriochlorins are generally less studied because their preparation poses multiple challenges. 20 Moreover, the porphyrinoid metal complexes frequently possess blue-shifted optical spectra, reduced long wavelengths absorptivities, and lower solubilities compared to their free bases. 28 We thus opted here for the study of the free base compounds.…”

Section: Resultsmentioning

confidence: 99%

“…19 Bacteriochlorins are characterized by UV-visible spectra with intense absorption bands in the near infrared (NIR) region (>700 nm). 20 These optical properties and their ability to generate singlet oxygen make bacteriochlorins very attractive for use as, for instance, photochemotherapeutics 21 or light-harvesting systems. 22 Preliminary reports on their use as PAI imaging agents have also appeared.…”

Section: Introductionmentioning

confidence: 99%

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The evaluation of NIR-absorbing porphyrin derivatives as contrast agents in photoacoustic imaging

Abuteen

Zanganeh

Akhigbe

et al. 2013

Phys. Chem. Chem. Phys.

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Six free base tetrapyrrolic chromophores, three quinoline-annulated porphyrins and three morpholinobacteriochlorins, that absorb light in the near-IR range and possess, in comparison to regular porphyrins, unusually low fluorescence emission and 1O2 quantum yields were tested with respect to their efficacy as novel molecular photo-acoustic imaging contrast agents in a tissue phantom, providing an up to ~2.5-fold contrast enhancement over that of the benchmark contrast agent ICG. The testing protocol compares the photoacoustic signal output strength upon absorption of approximately the same light energy. Some relationships between photophysical parameters of the dyes and the resulting photoacoustic signal strength could be derived.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The evaluation of NIR-absorbing porphyrin derivatives as contrast agents in photoacoustic imaging

Abuteen

Zanganeh

Akhigbe

et al. 2013

Phys. Chem. Chem. Phys.

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“…Several routes to synthetic bacteriochlorins have been developed (26)(27)(28)(29)(30)(31). The route we have developed affords bacteriochlorins that bear a geminal dimethyl group in each pyrroline ring and enables positioning of a wide variety of substituents at the b-pyrrole positions (10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20).…”

Section: Synthesismentioning

confidence: 99%

Integration of Cyanine, Merocyanine and Styryl Dye Motifs with Synthetic Bacteriochlorins

Yang

Zhang

Krayer

et al. 2015

Photochem & Photobiology

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Understanding the effects of substituents on spectral properties is essential for the rational design of tailored bacteriochlorins for light-harvesting and other applications. Toward this goal, three new bacteriochlorins containing previously unexplored conjugating substituents have been prepared and characterized. The conjugating substituents include two positively charged species, 2-(N-ethyl 2-quinolinium)vinyl- (B-1) and 2-(N-ethyl 4-pyridinium)vinyl- (B-2), and a neutral group, acroleinyl- (B-3); the charged species resemble cyanine (or styryl) dye motifs whereas the neutral unit resembles a merocyanine dye motif. The three bacteriochlorins are examined by static and time-resolved absorption and emission spectroscopy and density functional theoretical calculations. B-1 and B-2 have Qy absorption bathochromically shifted well into the NIR region (822 and 852 nm), farther than B-3 (793 nm) and other 3,13-disubstituted bacteriochlorins studied previously. B-1 and B-2 have broad Qy absorption and fluorescence features with large peak separation (Stokes shift), low fluorescence yields, and shortened S1 (Qy ) excited-state lifetimes (~700 ps and ~100 ps). More typical spectra and S1 lifetime (~2.3 ns) are found for B-3. The combined photophysical and molecular-orbital characteristics suggest the altered spectra and enhanced nonradiative S1 decay of B-1 and B-2 derive from excited-state configurations in which electron density is shifted between the macrocycle and the substituents.

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“…Many of these applications will greatly benefit from an inherent solubility of the porphyrins in aqueous media, i.e., not requiring any surfactants or liposome vesicles to mediate solubility. However, even though the methodologies toward synthetic porphyrins [29,30], hydroporphyrins [2,[31][32][33][34], and their analogues [34][35][36][37][38][39], have advanced enormously in the past decades, the vast majority of the synthetic porphyrinoids presented are not natively water-soluble, preventingor at least complicating-their utilization in, for example, biological contexts.…”

Section: Introductionmentioning

confidence: 99%

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

Luciano

Brückner

2017

Preprint

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Abstract:The increasing popularity of porphyrins and hydroporphyrins for application in a variety of biomedical (photodynamic therapy, fluorescence tagging and imaging, photoacoustic imaging) and technical (chemosensing, catalysis, light harvesting) applications is also associated with the growing number of methodologies that enable their solubilization in aqueous media. Natively, the vast majority of synthetic porphyrinic compounds are not water-soluble. Moreover, any water-solubility imposes several restrictions on the synthetic chemist on when to install solubilizing groups in the synthetic sequence, and how to isolate and purify these compounds. This review summarizes the chemical modifications to render synthetic porphyrins water-soluble, with a focus on the work since 2000. Where available, practical data such as solubility, indicators for the degree of aggregation, and special notes for the practicioner are listed. We hope that this review will guide synthetic chemists through the many strategies known to make porphyrins and hydroporphyrins water soluble.

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76 Syntheses of Bacteriochlorins and Isobacteriochlorins

Cited by 58 publications

References 0 publications

The evaluation of NIR-absorbing porphyrin derivatives as contrast agents in photoacoustic imaging

The evaluation of NIR-absorbing porphyrin derivatives as contrast agents in photoacoustic imaging

Integration of Cyanine, Merocyanine and Styryl Dye Motifs with Synthetic Bacteriochlorins

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

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