Extension of π-system of silylated porphyrin derivative for photodynamic therapy

Horiuchi, Hiroaki; Sakai, Asumi; Akiyama, Shin-ichi; Ikeda, Remi; Ito, Satoshi; Furuya, Masaru; Gomibuchi, Yuta; Ichikawa, Muneki; Yoshihara, Toshitada; Tobita, Seiji; Okutsu, Tetsuo

doi:10.1016/j.jphotochem.2017.02.015

Cited by 11 publications

(11 citation statements)

References 27 publications

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“…Overall, the relative 1 O 2 quantum yields Δ rel ( 1 O 2 ), are found to be lower for TATBP than for TPP (compare Table S8). This observation is consistent with literature, which demonstrated that π‐extension enhances the relaxation through internal conversion . However, in perspective of biomedical relevance, these Δ rel ( 1 O 2 ) values are misleading.…”

Section: Resultssupporting

confidence: 89%

“…All TATBPs synthesized in this work show the typical absorption and emission features (see Supporting Information), which have already been described in literature . However, the majority of publications describes the characteristics of metallated species .…”

Section: Resultssupporting

confidence: 53%

“…However, in perspective of biomedical relevance, these Δ rel ( 1 O 2 ) values are misleading. Earlier reports showed that π‐extension has a positive effect on the photodynamic activity . As depicted in Figure c, the DPBF‐bleaching rate constant k b is significantly larger for the investigated TATBP compared to TPP , and thus more 1 O 2 is produced in the same time period .…”

Section: Resultsmentioning

confidence: 66%

“…This observation is consistent with literature, which demonstrated that p-extension enhances the relaxation through internal conversion. [61,64] However,i np erspective of biomedical relevance, these D rel ( 1 O 2 )v alues are misleading. Earlier reports showedt hat p-extension has ap ositive effect on the photodynamic activity.…”

Section: Singlet Oxygen Formationmentioning

confidence: 99%

“…[80] Optoelectronics All TATBPs synthesized in this work show the typical absorption and emission features (see Supporting Information), which have already been described in literature. [60,61] However,t he majority of publications describes the characteristicso fm etallated species. [12,13,15,24,26,[62][63][64][65] In the following, the influence of the substituents in the aryl group with respectt ot heir positions and electronic nature is highlighted by means of absorption spectroscopy.At able summarizing the relative oscillator strength of all compounds is shown in the Supporting Information (Table S6).…”

Section: Structural Analysismentioning

confidence: 99%

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A Comprehensive Study on Tetraaryltetrabenzoporphyrins

Ruppel

Lungerich

Sturm

et al. 2020

Chemistry A European J

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Tetraaryltetrabenzoporphyrins (TATBPs) show, due to their optoelectronic properties, rising potential as dyes in various fields of physical and biomedical sciences. However, unlike in the case of porphyrins, the potential structural diversity of TATBPs has been explored only to little extent, owed mainly to synthetic hurdles. Herein, we prepared a comprehensive library of 30 TATBPs and investigated their fundamental properties. We elucidated structural properties by X‐ray crystallography and found explanations for physical properties such as solubility. Fundamental electronic aspects were studied by optical spectroscopy as well as by electrochemistry and brought in context to the stability of the molecules. Finally, we were able to develop a universal synthetic protocol, utilizing a readily established isoindole synthon, which gives TATBPs in high yields, regardless of the nature of the used arylaldehyde and without meticulous chromatographic purifications steps. This work serves as point of orientation for scientists, that aim to utilize these molecules in materials, nanotechnological, and biomedical applications.

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Section: Resultssupporting

confidence: 89%

Section: Resultssupporting

confidence: 53%

Section: Resultsmentioning

confidence: 66%

Section: Singlet Oxygen Formationmentioning

confidence: 99%

Section: Structural Analysismentioning

confidence: 99%

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A Comprehensive Study on Tetraaryltetrabenzoporphyrins

Ruppel

Lungerich

Sturm

et al. 2020

Chemistry A European J

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π‐Extended Donor–Acceptor Porphyrins and Metalloporphyrins for Antimicrobial Photodynamic Inactivation

Galstyan

Maurya

Zhylitskaya

et al. 2020

Chemistry A European J

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Free base, zinc and palladium π‐extended porphyrins containing fused naphthalenediamide units were employed as photosensitizers in antimicrobial photodynamic therapy (aPDT). Their efficacy, assessed by photophysical and in vitro photobiological studies on Gram‐positive bacteria, was found to depend on metal coordination, showing a dramatic enhancement of photosensitizing activity for the palladium complex.

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