A<sub>3</sub>B‐Type Phthalocyanine‐Based Homoleptic Lanthanide(III) Double‐Decker π‐Radical Complexes Bearing Functional Hydroxy Groups: Synthetic Approach, Spectral Properties and Electrochemical Study

Pushkarev, Victor E.; Tolbin, Alexander Yu.; Borisova, Nataliya E.; Trashin, Stanislav; Tomilova, Larisa G.

doi:10.1002/ejic.201000511

Cited by 41 publications

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“…[13,53] We have performed demetallation of the prepared Mg complexes under acidic conditions to prepare metal-free dimeric phthalocyanines (Scheme 4). A variety of methods for the demetallation of Mg-phthalocyanines is reported, [61,64,65] which differ in origin of applied acid, from dissolution of the complex in concentrated sulphuric acid to reflux in acetic acid. We applied the mild conditions and performed the demetallation upon reflux either in 80 % acetic acid or 5 % trifluoroacetic acid in chloroform.…”

Section: (24-сrown-8)-linked Dimeric Phthalocyanines and Their Metal mentioning

confidence: 99%

(24-Сrown-8)-Linked Dimeric Phthalocyanines and Their Metal Complexes

Birin¹,

Chugunov²,

Krapivenko³

et al. 2014

MHC

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Section: (24-сrown-8)-linked Dimeric Phthalocyanines and Their Metal mentioning

confidence: 99%

(24-Сrown-8)-Linked Dimeric Phthalocyanines and Their Metal Complexes

Birin¹,

Chugunov²,

Krapivenko³

et al. 2014

MHC

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“…(Scheme 14) have been prepared using synthetic conditions [219] developed for systems 54 [102]. These complexes were further used as precursors for preparation of the nano-sized rareearth systems.…”

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confidence: 99%

Historic overview and new developments in synthetic methods for preparation of the rare-earth tetrapyrrolic complexes

Pushkarev

Tomilova

Nemykin

2016

Coordination Chemistry Reviews

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New developments as well as a historic overview on synthetic strategies for preparation of the rare-earth complexes with porphyrins, phthalocyanines, naphthalocyanines, tetraazaporphyrins, and related systems are discussed in detail with emphasis on selective synthetic pathways for preparation of single-, double, and triple-decker architectures. 6 IntroductionAfter their discovery almost 100 years ago, phthalocyanines (Pcs) were predominantly investigated because of their industrial applications as dyes, pigments, and catalysts [1][2][3].Similarly, historically, porphyrins (Pors) were intensively studied because of their importance in mimicking biologically relevant atom-and electron-transfer processes as well as light-harvesting mechanisms associated with living cells [4][5][6]. In addition, porphyrins, phthalocyanines, and their analogues were found to be useful in applications such as redox-driven fluorescence markers and biomarkers, light-harvesting antennas for organic photovoltaics and dye sensitized solar cells, charge carriers for copiers and printers, materials for molecular electronics, as well as redoxactive components in environmental, biological, and industrial sensors as well as active components in photodynamic therapy (PDT) and boron neutron therapy (BNT) of cancer [7][8][9][10][11][12][13][14][15][16][17][18][19].In their initial attempts, researchers focused on rich coordination, redox, and magnetic properties of the metal-free, main-group, and especially transition-metal porphyrinoids. It was soon realized, however, that the rare-earth ions can form unusual systems when coupled with the phthalocyanine ligand.The first rare-earth Pcs were reported by Russian scientists Kirin and Moskalev in 1965 [20]. Kirin and Moskalev also pointed out that because of the large ionic radii and high coordination numbers of the rare-earth ions, the formation of the double-decker rare-earth phthalocyanine compounds could be achieved under specific reaction conditions [20,21]. During the next 50 years, it was confirmed that rare-earth ions are capable of the formation of phthalocyanine single-, double, and triple-decker complexes and their analogues [22][23][24][25][26][27][28][29][30][31][32][33]. One of the interesting recent discoveries was the preparation and characterization of heteronuclear (rareearth / cadmium) multiple-decker complexes, which contain up to six Pc ligands [34][35][36][37][38][39][40][41][42].

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“…The 2‐ureido‐4[1H]‐pyrimidinone unit was found to be unstable under the harsh reaction conditions for both phthalocyanine and TbPc 2 synthesis, therefore its introduction after complex formation (postfunctionalization) is mandatory. To insert a single functionality on the TbPc 2 scaffold the complex was prepared starting from A 3 B‐type phthalocyaninato ligand Pc‐NPhth ( Figure ). Since phthalimide, used as protecting group for the amine, is known to be unstable under phthalocyanine formation conditions, this functionality was introduced via Williamson reaction of the mono‐hydroxyl phthalocyanine Pc‐OH .…”

Section: Resultsmentioning

confidence: 99%

Self‐Assembly of TbPc₂ Single‐Molecule Magnets on Surface through Multiple Hydrogen Bonding

Pedrini

Poggini

Tudisco

et al. 2017

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A₃B‐Type Phthalocyanine‐Based Homoleptic Lanthanide(III) Double‐Decker π‐Radical Complexes Bearing Functional Hydroxy Groups: Synthetic Approach, Spectral Properties and Electrochemical Study

Abstract: Pc = 2-benzyloxy-9,10,16,17,23,24-hexa-n- Pc = 9,10,16,17,23,24-hexa-nbutyl-2-hydroxyphthalocyaninate) (2a, 2b), which are prom-

Cited by 41 publications

References 29 publications

(24-Сrown-8)-Linked Dimeric Phthalocyanines and Their Metal Complexes

(24-Сrown-8)-Linked Dimeric Phthalocyanines and Their Metal Complexes

Historic overview and new developments in synthetic methods for preparation of the rare-earth tetrapyrrolic complexes

Self‐Assembly of TbPc₂ Single‐Molecule Magnets on Surface through Multiple Hydrogen Bonding

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A3B‐Type Phthalocyanine‐Based Homoleptic Lanthanide(III) Double‐Decker π‐Radical Complexes Bearing Functional Hydroxy Groups: Synthetic Approach, Spectral Properties and Electrochemical Study

Abstract: Pc = 2-benzyloxy-9,10,16,17,23,24-hexa-n- Pc = 9,10,16,17,23,24-hexa-nbutyl-2-hydroxyphthalocyaninate) (2a, 2b), which are prom-

Cited by 41 publications

References 29 publications

(24-Сrown-8)-Linked Dimeric Phthalocyanines and Their Metal Complexes

(24-Сrown-8)-Linked Dimeric Phthalocyanines and Their Metal Complexes

Historic overview and new developments in synthetic methods for preparation of the rare-earth tetrapyrrolic complexes

Self‐Assembly of TbPc2 Single‐Molecule Magnets on Surface through Multiple Hydrogen Bonding

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A₃B‐Type Phthalocyanine‐Based Homoleptic Lanthanide(III) Double‐Decker π‐Radical Complexes Bearing Functional Hydroxy Groups: Synthetic Approach, Spectral Properties and Electrochemical Study

Self‐Assembly of TbPc₂ Single‐Molecule Magnets on Surface through Multiple Hydrogen Bonding