Synthesis and Spectral Properties of <i>gem</i>‐Dimethyl Chlorin Photosensitizers

Melissari, Zoi; Sample, Harry C.; Twamley, Brendan; Williams, René M.; Senge, Ma­thias O.

doi:10.1002/cptc.202000051

Cited by 14 publications

(18 citation statements)

References 68 publications

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“…Chlorins are tetrapyrrolic structures, similar to porphyrins, except that one of the pyrrole rings is reduced. It was shown that the Zn(II) chlorin Chlorin-2 displayed an increased ISC rate, a higher triplet excited state quantum yields and a more efficient 1 O2 generation than its free-base counterpart Chlorin-1 as a result of the internal HAE [63]. Experimental results shown in ethanol [63].…”

Section: Bodipys and The Heavy Atom Effectmentioning

confidence: 96%

Metal Coordination Effects on the Photophysics of Dipyrrinato Photosensitizers

Teeuwen¹,

Melissari²,

Senge³

et al. 2022

Preprint

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Within this work we review the metal coordination effect on the photophysics of metal dipyrrinato complexes. Dipyrrinato complexes are promising candidates in the search for alternative transition metal photosensitizers for application in photodynamic therapy (PDT). These complexes can be activated by irradiation with light of a specific wavelength, after which cytotoxic reactive oxygen species (ROS) are generated. The metal coordination allows for the use of the heavy atom effect, which can enhance the triplet generation necessary for generation of ROS. Additionally, the flexibility of these complexes for metal ions, substitutions and ligands allows the possibility to tune their photophysical properties. A general overview of the mechanism of photodynamic therapy and the properties of the triplet photosensitizers is given, followed by further details of dipyrrinato complexes described in the literature that show relevance as photosensitizers for PDT. In particular, the photophysical properties of Re(I), Ru(II), Ir(III), Ni(II), Cu(II), Pd(II), Pt(II), Zn(II), Ga(III), In(III), Al(III), Sn(II), and P dipyrrinato complexes are discussed. The potential for future development in the field of (dipyrrinato)metal complexes is addressed and several new research topics are suggested throughout this work. We propose that significant advances could be made for heteroleptic bis(dipyrrinato)zinc(II) and homoleptic bis(dipyrrinato)palladium(II) complexes and their application as photosensitizers for PDT.

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Section: Bodipys and The Heavy Atom Effectmentioning

confidence: 96%

Metal Coordination Effects on the Photophysics of Dipyrrinato Photosensitizers

Teeuwen¹,

Melissari²,

Senge³

et al. 2022

Preprint

Self Cite

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“…18 It is well established that the introduction of halogen atoms or transition metals can enhance the efficiency of this ISC, and therefore the triplet and singlet oxygen quantum yield. 50 The fluorescence lifetimes revealed a single exponential decay, suggesting the presence of only one population (for more detailed results please see the ESI, † Fig. S19).…”

Section: Papermentioning

confidence: 99%

“…33 Some research studies describe that the macrocycle distortion from the planarity and enhanced conformational dynamics can induce some destabilization of the π-system, which may lead to considerably shorter lifetimes. 50 Considering that the insertion of the metal ion can influence the thermal behaviour of the heterocyclic-fused chlorins, a thermal decomposition/sublimation study by TGA of the free-base and metal-complexes for the pyrrolidine and isoxazolidine-fused chlorins was carried out. The thermograms of the pyrrolidine and isoxazolidine-fused metallochlorins are presented in Fig.…”

Section: Papermentioning

confidence: 99%

Ohmic heating-assisted synthesis and characterization of Zn(ii), Cu(ii) and Pd(ii) complexes of heterocyclic-fused chlorins

et al. 2022

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“…Chlorins are tetrapyrrolic structures, similar to porphyrins, except that one of the pyrrole rings is reduced. It was shown that the Zn(II) chlorin Chlorin-2 displayed an increased ISC rate, a higher triplet excited state quantum yields and a more efficient 1 O 2 generation than its free-base counterpart Chlorin-1 as a result of the internal HAE [ 63 ].…”

Section: The Heavy Atom Effect In Bodipys and Chlorinsmentioning

confidence: 99%

“…These methods can predict the structural, energetic, and spectroscopic properties of compounds for the ground-state and excited-state properties of PSs. First, the geometry of the relevant compound is optimized, using a certain functional (usually a hybrid functional such as B3LYP or M06 [ 63 , 85 ]) and a basis set. Generally, basis sets leading to more accurate results cost significantly more computational effort.…”

Section: Transition Metal Triplet Photosensitizersmentioning

confidence: 99%

Metal Coordination Effects on the Photophysics of Dipyrrinato Photosensitizers

et al. 2022

View full text Add to dashboard Cite

Within this work, we review the metal coordination effect on the photophysics of metal dipyrrinato complexes. Dipyrrinato complexes are promising candidates in the search for alternative transition metal photosensitizers for application in photodynamic therapy (PDT). These complexes can be activated by irradiation with light of a specific wavelength, after which, cytotoxic reactive oxygen species (ROS) are generated. The metal coordination allows for the use of the heavy atom effect, which can enhance the triplet generation necessary for generation of ROS. Additionally, the flexibility of these complexes for metal ions, substitutions and ligands allows the possibility to tune their photophysical properties. A general overview of the mechanism of photodynamic therapy and the properties of the triplet photosensitizers is given, followed by further details of dipyrrinato complexes described in the literature that show relevance as photosensitizers for PDT. In particular, the photophysical properties of Re(I), Ru(II), Rh(III), Ir(III), Zn(II), Pd(II), Pt(II), Ni(II), Cu(II), Ga(III), In(III) and Al(III) dipyrrinato complexes are discussed. The potential for future development in the field of (dipyrrinato)metal complexes is addressed, and several new research topics are suggested throughout this work. We propose that significant advances could be made for heteroleptic bis(dipyrrinato)zinc(II) and homoleptic bis(dipyrrinato)palladium(II) complexes and their application as photosensitizers for PDT.

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Synthesis and Spectral Properties of gem‐Dimethyl Chlorin Photosensitizers

Cited by 14 publications

References 68 publications

Metal Coordination Effects on the Photophysics of Dipyrrinato Photosensitizers

Metal Coordination Effects on the Photophysics of Dipyrrinato Photosensitizers

Ohmic heating-assisted synthesis and characterization of Zn(ii), Cu(ii) and Pd(ii) complexes of heterocyclic-fused chlorins

Metal Coordination Effects on the Photophysics of Dipyrrinato Photosensitizers

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