A first archetype of boron dipyrromethene-phthalocyanine pentad dye: design, synthesis, and photophysical and photochemical properties

Göl, Cem; Malkoç, Mustafa; Yeşilot, Serkan; Durmuş, Mahmut

doi:10.1039/c4dt00406j

Cited by 29 publications

(14 citation statements)

References 38 publications

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“…The trends in the MO energies of the frontier π -MOs and in the HOMO-LUMO gaps of the analogous set of fused-ring-expanded phthalonitriles (39)(40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54), shown in Figure 7, are also broadly similar to those predicted for the corresponding Pc (1-22) and aza-BODIPY (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38) analogues. The alignments of the nodal planes of the a and s MOs (Figure 8) are similar to those of the corresponding tetraazapophyrin analogues (Figure 3), as would be anticipated based on their radial symmetry and the manner in which the 4 angular nodal planes lie on alternating sets of 8 atoms on the inner perimeter due to the M L = ± 4 properties.…”

Section: Resultssupporting

confidence: 55%

“…Figure 7. The MO energies predicted for maleonitrile(39), phthalonitrile(40), and structural analogues fused-ringexpanded at the pyrrole β -carbons with benzene (41), 2,3-naphthalene(42), phenanthrene(43), and phenanthroline (44) moieties, and β , β -tetrapyrazino-substituted phthalonitrile(45), and analogues fused-ring-expanded with benzene (46), 2,3-naphthalene (47), phenanthrene(48), and phenanthroline (49) moieties, and the corresponding β , βtetrabenzopyrazino-substituted structures(50)(51)(52)(53)(54). Bolder black lines are used to highlight the 4 frontier π -MOs that are associated with Michl's perimeter model.16−19 Black triangles and circles are used to denote the a/-a and s/-s MOs, respectively.…”

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confidence: 99%

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TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications

Mack¹,

Wildervanck

Nyokong

2014

Turk J Chem

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Geometry optimizations and TD-DFT calculations have been carried out on series of fused-ring-expanded phthalonitriles, phthalocyanines, and aza-dipyrromethene boron difluoride (aza-BODIPY) dyes and trends in their optical and redox properties have been analyzed. The potential utility of fused-ring-expanded phthalocyanine and aza-BODIPY analogues for photodynamic therapy and near infrared region sensor applications is assessed on this basis. Recent attempts to prepare fused-ring-expanded aza-BODIPY analogues with benzene, pyrazine, and naphthalene rings have demonstrated that the properties of aza-BODIPYs vary markedly when different fused ring systems are added to the β -carbons of the pyrrole rings. A comparison of the TD-DFT calculations demonstrates that, as has previously been postulated, trends in the optical spectra, redox properties, and electronic structures of aza-BODIPYs follow those observed for the phthalonitrile precursors and the analogous phthalocyanines despite the absence of a fully conjugated macrocyclic perimeter that obeys Hückel's rule.

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Section: Resultssupporting

confidence: 55%

mentioning

confidence: 99%

TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications

Mack¹,

Wildervanck

Nyokong

2014

Turk J Chem

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“…A new type of pentadiene phthalocyanine 97 containing four blocks of boron dipyrromethene (BODIPY) at the peripheral positions of the phthalocyanine skeleton was developed and synthesized for the first time [69] (Scheme 52). Two different synthesis strategies were used to synthesize the target dye BODIPY-Zn(II)Pc pentade.…”

Section: Axially Coordinated Bodipy-pc Conjugatesmentioning

confidence: 99%

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

et al. 2022

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Fluorescent dyes absorbing and emitting in the visible and near-IR regions are promising for the development of fluorescent probes for labeling and bio-visualization of body cells. The ability to absorb and emit in the long-wavelength region increases the efficiency of recording the spectral signals of the probes due to the higher permeability of the skin layers. Compared to other fluorescent dyes, BODIPYs are attractive due to their excellent photophysical properties–narrow absorption and emission, intense fluorescence, simple signal modulation for the practical applications. As part of conjugates with biomolecules, BODIPY could act as a biomarker, but as therapeutic agent, which allows solving several problems at once-labeling or bioimaging and treatment based on the suppression of pathogenic microflora and cancer cells, which provides a huge potential for practical application of BODIPY conjugates in medicine. The review is devoted to the discussion of the recent, promising directions of BODIPY application in the field of conjugation with biomolecules. The first direction is associated with the development of BODIPY conjugates with drugs, including compounds of platinum, paclitaxel, chlorambucil, isoxazole, capsaicin, etc. The second direction is devoted to the labeling of vitamins, hormones, lipids, and other biomolecules to control the processes of their transport, localization in target cells, and metabolism. Within the framework of the third direction, the problem of obtaining functional optically active materials by conjugating BODIPY with other colored and fluorescent particles, in particular, phthalocyanines, is being solved.

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“…Therefore, a decrease in energy of excited electrons declined the charge carriers recombination's rate [34]. Consequently, the photoinduced electron-transfer reactions lead to the generation of strong oxidative species such as • OH, ‾O2, and +• O2H that are essential for photocatalytic dye degradation [35].…”

Section: Introductionmentioning

confidence: 99%

Predominant role of grafted iron(III) Schiff-base complex in oxidation of gaseous and aqueous reactants: A visible light responsive photocatalyst

Tabari

Jamali

2017

Journal of Photochemistry and Photobiology A: Chemistry

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The visible light response and photocatalytic activities of covalently bonded iron(III)-Schiff base complex is evaluated by photooxidation of nitric oxide under visible light exposure. In addition, this study reports the existing of dominant active sites on the surface of grafted complex toward water adsorption, which leads to the generation of hydroxyl radicals under illumination. Moreover, the morphological analysis exhibits high surface area (575 m 2 /g) with an average pore diameter of 21 nm; in this context, XRD analysis shows that the characteristic peaks of the Schiff-base complex are covered by the amorphous structure of the silica network, however, the microscopic analysis reveals the irregular shape of the grafted catalyst. Furthermore, the catalytic activity was evaluated by photooxidation of reactive blue 13 dye in aqueous solution under ambient light illumination. Also, the reaction variables such as the amount of catalyst, pH value, concentration and temperature of the dye solution were studied and discussed in detail. It seems, the enhanced activity of the photocatalyst toward the dye decolourization is a consequence of its uniform surface, large surface area, fine particles and active surface for the water adsorption.

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A first archetype of boron dipyrromethene-phthalocyanine pentad dye: design, synthesis, and photophysical and photochemical properties

Cited by 29 publications

References 38 publications

TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications

TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications

BODIPY Conjugates as Functional Compounds for Medical Diagnostics and Treatment

Predominant role of grafted iron(III) Schiff-base complex in oxidation of gaseous and aqueous reactants: A visible light responsive photocatalyst

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