An Easy Route for the Synthesis of New Axially Substituted Titanium(IV) Phthalocyanines

Barthel, Markus J.; Dini, Danilo; Vagin, Sergei I.; Hanack, Michael

doi:10.1002/1099-0690(200211)2002:22<3756::aid-ejoc3756>3.0.co;2-4

Cited by 65 publications

(62 citation statements)

References 20 publications

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“…The choice of Ti as a central metal allows axial ligation to the metal center, as reported previously, 5,6 the axial ligand being employed to anchor the dye to the nanocrystalline particles and to prevent the aggregation of the macrocycles. On the other hand, the bulky peripheral tert-butyl substituents help to solubilise the dye in common organic solvents and to avoid dye aggregation.…”

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State selective electron injection in non-aggregated titanium phthalocyanine sensitised nanocrystalline TiO₂films

et al. 2004

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We describe a novel titanium phthalocyanine that shows no aggregation when anchored to nanocrystalline TiO 2 films through its axial carboxylated ligand without the use of coadsorbents; state selective electron injection into the TiO 2 is demonstrated, resulting in efficient photocurrent generation in dye sensitised photoelectrochemical solar cells.The dye sensitisation of wide-band gap nanocrystalline semiconductors is attracting renewed interest due to the development of efficient photoelectrochemical solar cells 1 based on ruthenium bipyridyl dyes. The efficiency of these devices is, however, significantly limited by the low optical absorbance of such dyes in the red/near infrared spectral regions. Hence, extensive research efforts are targeting new sensitiser dyes with stronger absorbance over this spectral region.Phthalocyanines (Pc) are well known chromophores for their intense absorption in the UV/blue (Soret band) and the red/near IR (Q band) spectral regions, as well as for their electrochemical, photochemical and thermal stability. They are therefore attractive as sensitiser dyes for dye sensitised solar cells (DSSC's), 2 as well as other photovoltaic devices.3 However, the applications of Pc dyes in DSSC's to date have been limited due to problems associated with aggregation of the dye on the metal oxide surface. Moreover, phthalocyanines suitable for DSSC's typically have a poor solubility in organic solvents, and a strong tendency to aggregate on the film surface, resulting in rapid deactivation of the dye excited state and low sensitising efficiency. Several groups 2,4 have studied the co-adsorption of small organic acids with the Pc sensitiser to minimise the aggregation process, resulting in a limited improvement in device performance.Here we report the synthesis of a new titanium phthalocyanine (TiPc) and its application to the sensitisation of nanocrystalline, mesoporous TiO 2 films. The choice of Ti as a central metal allows axial ligation to the metal center, as reported previously, 5,6 the axial ligand being employed to anchor the dye to the nanocrystalline particles and to prevent the aggregation of the macrocycles. On the other hand, the bulky peripheral tert-butyl substituents help to solubilise the dye in common organic solvents and to avoid dye aggregation. Using this axial ligation approach we are, moreover, able to control the distance between the HOMO orbital of the chromophore and the TiO 2 surface and thereby the electron injection and recombination dynamics.Titanium(IV) tetra(tert-butyl)phthalocyanine (TiPc) was synthesised according to a literature procedure 5 and characterised by 1 H NMR and UV-Vis spectroscopies, MALDI-TOF spectrometry and elemental analysis.The compound TiPc showed electrochemical stability, with reversible dye oxidation being observed with a mid-point potential of 0.950 V vs. Ag/AgCl. The solution absorption spectrum showed the expected intense Q-band absorption transition (l max~7 02 nm, e~135 000 dm 3 mol 21 cm 21). ZINDO/1 semi-empirical calculations indic...

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“…Titanium(IV) tetra(tert-butyl)phthalocyanine (TiPc) was synthesised according to a literature procedure 5 and characterised by 1 H NMR and UV-Vis spectroscopies, MALDI-TOF spectrometry and elemental analysis.…”

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State selective electron injection in non-aggregated titanium phthalocyanine sensitised nanocrystalline TiO₂films

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“…In the current study, we investigated and clarified the antioxidant properties of the synthesized MPCs, because of the relevance of these compounds in the contexts of oxidative stress, disease etiology, and for the progress of medicine 25 . Thus we considered that it was worthwhile to study the potential aspects of these new copper, cobalt and nickel phthalocyanines carrying four 2(2-methoxyphenyl)ethanol and 3-Hydroxybenzaldehyde groups on the peripheral positions 3-8 for antioxidant activity according to our initial planning.…”

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Synthesis, Characterization, Aggregation behaviors, Antioxidant and Anti-inflammatory activities of Unmetalled and metallophthalocyanines bearing 2(3,4-dimethoxyphenyl)ethanol and 4-Hydroxybenzaldehyde groups

Sulaiman¹

2016

Mediterr.J.Chem.,

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Novel metallophthalocyanines (M: Co, Cu, Ni) containing 2(2-methoxyphenyl)ethanol and 3-Hydroxybenzaldehyde groupsÂ were synthesized and characterized.The structures were confirmed by IR, UV/vis, 1H NMR, 13C NMR, mass spectroscopy Â and elemental analysis. The aggregation behavior of these compounds was investigated in DMSO.Â In addition; the compounds 4-9 were investigated for anti-oxidant activities by super oxide radical; DPPH (2,2-Diphenyl-1-picrylhydrazyl); and hydroxyl radical scavenging assays; in which most of themÂ displayed significant antioxidant activities. Furthermore; compounds 4-9Â Â were evaluated for anti-inflammatory activity by indirect hemolytic and lipoxygenase inhibition assays and revealed good activity.

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“…shown by some phthalocyaninatotitanium(IV) complexes characterized by different kinds of axial ligands X [21,22]. The R y PcTiX n species whose OL properties are here investigated are listed in Table 1 and the references concerning the details of their preparation are given in the last column of the table.…”

Section: Synthesis Of Conjugated Macrocycle-metal Complexesmentioning

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Conjugated Molecules for the Smart Filtering of Intense Radiations

Dini

2003

IJMS

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Abstract:The practical realization of smart optical filters, i.e. devices which change their optical transmission in a suitable way to keep a working state for a general light sensitive element , can involve the use of conjugated molecules whose light absorption properties are light-intensity dependent (nonlinear optical effect). The verification of optical limiting displayed by some particular conjugated molecules, e.g. phthalocyanines, is quite noteworthy and can be successfully exploited for the realization of such smart optical devices. In the present contribution the analysis of the relevant molecular feature of a phthalocyanine are analyzed with the aim of determining useful correlations between optical limiting performance and phthalocyanine chemical structure. In particular , the electronic nature of the substituent is considered as a key factor for the explanation of some observed optical limiting trends.

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An Easy Route for the Synthesis of New Axially Substituted Titanium(IV) Phthalocyanines

Cited by 65 publications

References 20 publications

State selective electron injection in non-aggregated titanium phthalocyanine sensitised nanocrystalline TiO₂films

State selective electron injection in non-aggregated titanium phthalocyanine sensitised nanocrystalline TiO₂films

Synthesis, Characterization, Aggregation behaviors, Antioxidant and Anti-inflammatory activities of Unmetalled and metallophthalocyanines bearing 2(3,4-dimethoxyphenyl)ethanol and 4-Hydroxybenzaldehyde groups

Conjugated Molecules for the Smart Filtering of Intense Radiations

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An Easy Route for the Synthesis of New Axially Substituted Titanium(IV) Phthalocyanines

Cited by 65 publications

References 20 publications

State selective electron injection in non-aggregated titanium phthalocyanine sensitised nanocrystalline TiO2films

State selective electron injection in non-aggregated titanium phthalocyanine sensitised nanocrystalline TiO2films

Synthesis, Characterization, Aggregation behaviors, Antioxidant and Anti-inflammatory activities of Unmetalled and metallophthalocyanines bearing 2(3,4-dimethoxyphenyl)ethanol and 4-Hydroxybenzaldehyde groups

Conjugated Molecules for the Smart Filtering of Intense Radiations

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State selective electron injection in non-aggregated titanium phthalocyanine sensitised nanocrystalline TiO₂films

State selective electron injection in non-aggregated titanium phthalocyanine sensitised nanocrystalline TiO₂films