X-ray crystal structure of [2,7,12,17-tetrapropylporphycenato]platinum(II). A comparison of nickel(II) and platinum(II) porphycene

Ming, Chi; Cheung, Ka Shing; Li, Zao Ying; Wong, Kwok Yin; Yu, Wei

doi:10.1016/s0277-5387(00)83100-9

Cited by 13 publications

(4 citation statements)

References 8 publications

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“…Other less frequently studied metalloporphycenes are those containing rhenium ( 231 and 232 , Scheme ), osmium ( 234 and 235 , Scheme ), indium ( 223 , Scheme ), platinum ( 13 ), , molybdenum ( 19 ), and magnesium ( 19 ) …”

Section: Electronic Spectroscopymentioning

confidence: 99%

Spectroscopy and Tautomerization Studies of Porphycenes

2016

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Tautomerization in porphycenes, constitutional isomers of porphyrins, is strongly entangled with spectral and photophysical parameters. The intramolecular double hydrogen transfer occurring in the ground and electronically excited states leads to uncommon spectroscopic characteristics, such as depolarized emission, viscosity-dependent radiationless depopulation, and vibrational-mode-specific tunneling splittings. This review starts with documentation of the electronic spectra of porphycenes: Absorption and magnetic circular dichroism are discussed, together with their analysis based on the perimeter model. Next, photophysical characteristics are presented, setting the stage for the final part, which discusses the developments in research on tautomerism. Porphycenes have been studied in different experimental regimes: molecules in condensed phases, isolated in supersonic jets and helium nanodroplets, and, recently also on the level of single molecules investigated by optical and scanning probe microscopies. Because of the rich and detailed information obtained from these diverse investigations, porphycenes emerge as very good models for studying the complex, multidimensional phenomena involved in the process of intramolecular double hydrogen transfer.

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Section: Electronic Spectroscopymentioning

confidence: 99%

Spectroscopy and Tautomerization Studies of Porphycenes

2016

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“…Although porphycenes are poorer ligands than porphyrins, they also form complexes with a variety of metals [124,160,[180][181][182][183][184][185][186][187][188][189][190][191][192][193]. The absorption spectra of metalloporphycenes have both similarities and differences compared to the free base: while the Soret band position is virtually unchanged, the three Q-bands are reduced to two as a result of the increase in symmetry, and the lowest-energy Q-band suffers a hypsochromic shift that reflects electron donation from the metal into the porphycene, thus raising its energy.…”

Section: Absorption Spectramentioning

confidence: 99%

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Stockert¹,

Cañete²,

Juarranz³

et al. 2007

CMC

177

130

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The photodynamic process induces cell damage and death by the combined effect of a photosensitizer (PS), visible light, and molecular oxygen, which generate singlet oxygen ((1)O(2)) and other reactive oxygen species that are responsible for cytotoxicity. The most important application of this process with increasing biomedical interest is the photodynamic therapy (PDT) of cancer. In addition to hematoporphyrin-based drugs, 2nd generation PSs with better photochemical properties are now studied using cell cultures, experimental tumors and clinical trials. Porphycene is a structural isomer of porphyrin and constitutes an interesting new class of PS. Porphycene derivatives show higher absorption than porphyrins in the red spectral region (lambda > 600 nm, epsilon > 50000 M-(1)cm(-1)) owing to the lower molecular symmetry. Photophysical and photobiological properties of porphycenes make them excellent candidates as PSs, showing fast uptake and diverse subcellular localizations (mainly membranous organelles). Several tetraalkylporphycenes and the tetraphenyl derivative (TPPo) induce photodamage and cell death in vitro. Photodynamic treatments of cultured tumor cells with TPPo and its palladium(II) complex induce cytoskeletal changes, mitotic blockage, and dose-dependent apoptotic or necrotic cell death. Some pharmacokinetic and phototherapeutic studies on experimental tumors after intravenous or topical application of lipophilic alkyl-substituted porphycene derivatives are known. Taking into account all these features, porphycene PSs should be very useful for PDT of cancer and other biomedical applications.

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“…For example, strong hydrogen bonding is found to make the ligand more rectangular in nature; as a result, the orientation of nitrogen lone pairs less is favorable for metal coordination. This was clearly evident in type A and type B porphycenes having substituents at the meso - and outer-β-pyrrolic positions, respectively (Figure ), where coordination with metal ions was found to be difficult to perform. ,, Vogel found the presence of substituents at the 3,6,13,16-positions in β-octaalkylporphycenes reduced the strength of the NH···N hydrogen bond owing to nonbonding interactions, thereby making the macrocyclic core more of a square-type . After more than three decades, we recently synthesized the first 3,6,13,16-substituted porphycene (type C ), which was found to display slightly stronger NH···N hydrogen bonding than the type D analogues .…”

mentioning

confidence: 99%

In-Core N4-Coordination of Palladium(II) in Dinaphthoporphycene: Synthesis, Structure, and Photophysical Studies

Sahoo

Panda

2022

Inorg. Chem.

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Dinaphthoporphycene (DNP) has emerged as a versatile ligand undergoing large out-of-plane distortion to form a cis-bimetallic complex with Pd(II) using Pd(OAc)2 and out-of-plane monometallic complexes with Pd(acac)2 and PtCl2(PhCN)2. Herein, we are finally able to synthesize the in-core complex with Pd(II) using PdCl2(PhCN)2 or PdCl2. The crystal structure shows the palladium ion resides slightly above the N4-core, with the Pd(II) dimensionally dissenting with the typical square planarity displayed by the reported in-core DNP complexes with Ni(II) and Cu(II) ions. The deformed complex displays a blue shift in the absorption spectra compared to DNP and its metallo-derivatives. PdDNP exhibits a moderate singlet oxygen generation ability (18%).

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X-ray crystal structure of [2,7,12,17-tetrapropylporphycenato]platinum(II). A comparison of nickel(II) and platinum(II) porphycene

Cited by 13 publications

References 8 publications

Spectroscopy and Tautomerization Studies of Porphycenes

Spectroscopy and Tautomerization Studies of Porphycenes

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

In-Core N4-Coordination of Palladium(II) in Dinaphthoporphycene: Synthesis, Structure, and Photophysical Studies

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