Metallated Phthalocyanines as the Core of Dendrimers – Synthesis and Spectroscopic Studies

Leclaire, Julien; Dagiral, Rodolphe; Pla‐Quintana, Anna; Caminade, Anne‐Marie; Majoral, Jean‐Pierre

doi:10.1002/ejic.200601235

Cited by 28 publications

(21 citation statements)

References 22 publications

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“…Their non‐degenerate LUMO orbitals manifested themselves as a split band in the long‐wavelength UV/Vis region. As shown in the study by Leclaire et al., the presence of bulky dendritic substituents in the periphery of a macrocycle is responsible for shielding the tetrapyrrolic core and thus for an increase in the Q‐band intensity with every dendrimer generation added. In our study, the relative absorbance of the Q band of tribenzoporphyrazines 9 and 13 with G 0 and G 1 dendrimeric substituents of different size did not change significantly.…”

Section: Resultsmentioning

confidence: 94%

“…The possibility to add and modify dendrimer substituents at the periphery of macrocyclic rings has been applied so far for porphyrins and phthalocyanines . It has been shown that dendrimeric moieties around the porphyrinoid core significantly affect their photophysical characteristics . Dendrimers by themselves are highly branched polymers with unique physico‐chemical and biological properties .…”

Section: Introductionmentioning

confidence: 99%

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Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico‐Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

et al. 2016

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Sulfanyl porphyrazines substituted at their periphery with different dendrimeric moieties up to their first generation were synthesized and characterized by photochemical and biological methods. The presence of a dendrimeric periphery enhanced the spectral properties of the porphyrazines studied. The singlet‐oxygen‐generation quantum yield of the obtained macrocycles ranged from 0.02 to 0.20 and was strongly dependent on the symmetry of the compounds and the terminal groups of the dendritic outer shell. The in vitro biological effects of three most promising tribenzoporphyrazines were examined; the results indicated their potential as photosensitizers for photodynamic therapy (PDT) against two oral squamous cell carcinoma cell lines derived from the tongue. The highest photocytotoxicity was found for sulfanyl tribenzoporphyrazine that possessed 4‐[3,5‐di(hydroxymethyl)phenoxy]butyl substituents with nanomolar IC50 values at 10 and 42 nm against CAL 27 and HSC‐3 cell lines, respectively.

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Section: Resultsmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico‐Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

et al. 2016

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“…A phthalocyanine functionalized by eight aldehydes has been used as core for the synthesis of phosphorhydrazone dendrimers, using the process shown in Scheme 1. The process was carried out up to generation 5 from a free phthalocyanine, and up to generation 8 starting from its cobalt complex [10]. The phthalocyanine core was used for analyzing the properties of the internal structure and for determining the influence of each structural part (surface, branches, core) upon the whole structure, behaving as a sensitive sensor.…”

Section: Functional Cores Of Dendrimers (Type A)mentioning

confidence: 99%

Bifunctional Phosphorus Dendrimers and Their Properties

Caminade

Majoral

2016

Molecules

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Dendrimers are hyperbranched and monodisperse macromolecules, generally considered as a special class of polymers, but synthesized step-by-step. Most dendrimers have a uniform structure, with a single type of terminal function. However, it is often desirable to have at least two different functional groups. This review will discuss the case of bifunctional phosphorus-containing dendrimers, and the consequences for their properties. Besides the terminal functions, dendritic structures may have also a function at the core, or linked off-center to the core, or at the core of dendrons (dendritic wedges). Association of two dendrons having different terminal functions leads to Janus dendrimers (two faces). The internal structure can also possess functional groups on one layer, or linked to one layer, or on several layers. Finally, there are several ways to have two types of terminal functions, besides the case of Janus dendrimers: either each terminal function bears two functions sequentially, or two different functions are linked to each terminal branching point. Examples of each type of structure will be given in this review, as well as practical uses of such sophisticated structures in the fields of fluorescence, catalysis, nanomaterials and biology.

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“…Dendrimers of up to the eighth generation complexed with Co(II) were prepared to study the progressive influence of the branches on the core (Fig. The addition of subsequent generations did not show any further change, indicating that the influence of the branches on the core is limited up to this specific generation probably due to steric hindrance [44]. The addition of subsequent generations did not show any further change, indicating that the influence of the branches on the core is limited up to this specific generation probably due to steric hindrance [44].…”

Section: Porphyrin and Phthalocyanine-based Dendrimersmentioning

confidence: 99%

Metallodendrimers: Photophysical Properties and Related Applications

Franc

Kakkar

2010

Photochemistry and Photophysics of Polymer Materials

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Hyperbranched and monodispersed tree-like macromolecules that are commonly referred to as dendrimers [1][2][3][4][5][6] have been attracting tremendous attention due to their significant potential in designing novel materials for applications in material science, medicine, and catalysis. Dendrimers (Fig. 5.1) can be synthesized using two different iterative step-by-step synthetic methodologies: (1) a divergent approach that starts from a plurifunctional core and extends outward in a layer-by-layer fashion, as initially described by V€ ogtle and coworkers [7] and subsequently extended by Tomalia et al. [8] or (2) alternatively, using a less common convergent strategy that involves grafting dendrons onto the core [9][10][11].The flurry of activity that followed these initial reports has generated a wealth of these macromolecules [12], and much emphasis has subsequently shifted to understanding their structure-property relationships, and then, applying these principles to design goaloriented applications. In addition, during the past few years, intriguing fluorescence properties offered by dendrimers have been studied in detail, and have been extended to a wide range of applications such as light harvesting [13][14][15], two-photon absorption [16,17], labeling agents for biology [18][19][20][21], and in the design of efficient and competitive OLEDs [22][23][24][25]. Furthermore, investigations regarding dendrimers and their interactions with metals have also expanded at a fast pace. Metallodendrimers [4,[26][27][28], as they are generally called, are now an integral part of the main-stream dendritic macromolecules. Thesewell-defined architectures include metal complexes of varied forms as illustrated in Fig. 5.2. Metallodendrimers can be synthesized using a stepwisebuild-upapproachinwhichcoordination ligands bindtometals ofawidevariety that can be placed at the core, the periphery, and even as divergent points or a combination

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Metallated Phthalocyanines as the Core of Dendrimers – Synthesis and Spectroscopic Studies

Cited by 28 publications

References 22 publications

Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico‐Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico‐Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

Bifunctional Phosphorus Dendrimers and Their Properties

Metallodendrimers: Photophysical Properties and Related Applications

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