Photophysical properties of a water-soluble adjacently substituted bisnaphthalophthalocyanine

Abstract

Spectral properties of a water soluble metal free tetracarboxyphenoxy bisnaphthalophthalocyanine (3) were studied in water and organic solvents. It was found that in protic solvents, complex 3 was highly aggregated. The surfactant, Triton X100, and bovine serum albumin (BSA) do not effect disaggregation while cetyl trimethylammonium chloride (CTAC) caused the molecule to disaggregate. The fluorescence quantum yields were higher in the presence of CTAC. Studying the interaction of BSA with complex 3 using fluorometry revealed that BSA is highly quenched by the latter. A 1:1 stoichiometric binding ratio between BSA and the Pc was found. Triplet quantum yields in water containing CTAC were higher than in organic solvents.

Synthesis, spectroscopic, and cellular properties of α-pegylated cis-A2B2- and A3B-types ZnPcs

“…The reaction of bis-phthalonitrile 3 with various equivalents of phthalonitrile 4 (1–30 equiv) at 70–140 °C in dimethylaminoethanol (DMAE), in the presence of zinc(II) acetate and a catalytic amount of 1,5-diazabicyclo(4.3.0)non-5-ene (DBN) [18, 39], gave the A 2 B 2 - adjacent ZnPc 5 in up to 5% yield; ZnPcs 7 and 8 were also formed under the reaction conditions in 2–7% yields, similar to results previously published [44]. The formation of ZnPcs 7 and 8 in addition to 5 is a result of the higher flexibility of the 1,2-(dihydroxymethyl)benzene bridging group of 3 compared with the 2,2′-dihydroxy-1,1′-binaphthyl bridge previously reported [39–41, 46]. Deprotection of ZnPc 5 using concentrated H 2 SO 4 [47] gave the dihydroxy-dipegylated ZnPc 6 in 95% yield, while under similar conditions a mixture of ZnPcs 7 and 8 gave the monohydroxy-monopegylated ZnPc 9 in 41% yield.…”

Electrochemical, Spectroelectrochemical, and Electrocatalytic Dioxygen Reducing Properties of Peripheral Tetra‐2,6‐dimethoxyphenoxy Substituted Phthalocyanines

“…The novel Pc complexes (3-6) were then dried under vacuum. 3),9 (10), 16(17),23( 24 2.1.2.2 2(3),9 (10), 16(17), 23(24)-tetrakis-(2,6-dimethoxyphenoxy) phthalocyaninatoiron(III)acetate (4) The Fe(OAc)Pc ( 4) is soluble in DMSO, DMF, THF, toluene, CHCl (10), 16(17), 23(24)-tetrakis- (2,6-dimethoxyphenox) phthalocyaninatomanganese(III) acetate (5) The Mn(OAc)Pc (5)…”

“…The strong À C�N vibration at 2227 cm À 1 in the IR spectrum of the starting compound 1 was not observed in the spectra of metal-free Pc (2) and MPcs (3-6) which confirmed their formation. The vibrations bands were monitored at 3003-3081 cm À 1 for aromatic CÀ H stretching, 2832-2955 cm À 1 for aliphatic CÀ H stretching, 1716-1718 cm À 1 for aromatic C=O stretching (at Fe(OAc)Pc and Mn(OAc)Pc), 1639-1651 cm À 1 for aromatic C=N stretching, 1524-1602 cm À 1 for aromatic C=C stretching and 1200-1300 cm À 1 for ArÀ OÀ Ar stretching in the IR spectra of MPcs (3)(4)(5)(6).…”

“…Because of the exceptional chemical and thermal steadiness, Pc compounds have withdrawn high concern and have gained substantial place in many technological implementations in last tenner years [3]. Besides their traditional use, the usage of Pcs in various technological applications is extended to optical limiting devices, molecular electronics, liquid crystals, gas sensors, semiconductor materials, photovoltaic cells, photodynamic therapy (PDT) due to the above-mentioned excellent chemical and physical properties [1][2][3][4]. They have also attracted intensive attention because of broad applicability in the areas of materials chemistry and electrochemistry, including electrocatalysis, electrochromism, and energy conversion devices [4].…”

Synthetic approaches to asymmetric phthalocyanines and their analogues

“…Although formation of the other asymmetric and symmetric by-products in this reaction is unavoidable and thus purification of the target adjacent AABB phthalocyanines requires extensive chromatography steps, this method allows formation of rare AABB type compounds in a reasonably selective way. [156][157][158][159][160][161] Moreover, the key advantage of the use of the bis(phthalonitriles) with short rigid bridging groups similar to, for instance, 2,2′-dihydroxy-1.1′-binaphthyl, is suppressed formation of oligomeric phthalocyanines by the self-condensation reaction of such building blocks. …”