Electrochromic Switching of Evaporated Thin Films of Bulky, Electronic Deficient Metallo-Phthalocyanines

Nagel, S.; Lener, Martin; Keil, C.; Gerdes, Robert; Łapok, Łukasz; Gorun, Sergiu M.; Schlettwein, Derck

doi:10.1021/jp2010748

Cited by 56 publications

(41 citation statements)

References 36 publications

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“…Their characteristic B1 and B2 bands (3)(4)(5)(6)(7)(8)(9)(10) were observed at a range of 313-405 nm (Fig. 1).…”

Section: Syntheses and Characterizationmentioning

confidence: 96%

“…Because of their potential contribution to the next generation of molecular electronic devices such as electrochromic and electro-luminescent displays, nonlinear optics, photovoltaics, chemical sensors nanotechnology, and photosensitizers for photodynamic cancer therapy (PDT) of tumors, studies on the synthesis and characterization of novel phthalocyanines (Pcs) compounds are of considerable interest [1][2][3][4][5][6][7][8][9][10][11]. All the properties of Pcs are influenced and enhanced both by the nature of central metals and the substituent and substituent's position (peripheral or non-peripheral) in the Pc ring.…”

Section: Introductionmentioning

confidence: 99%

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Toluene vapor sensing characteristics of novel copper(II), indium(III), mono-lutetium(III) and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenoxy bioactive moieties

Pişkin

Can

Odabaş

et al. 2018

J. Porphyrins Phthalocyanines

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This study presents the synthesis, characterization and toluene sensing properties of copper(II), indium(III) acetate, mono-lutetium(III) acetate and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenol bioactive groups at the peripheral and non-peripheral positions. The effects of the substituent's position on the toluene vapor detection capabilities of these compounds were investigated. Adsorption data were analyzed by using first-order and Elovich equations in order to investigate the adsorption kinetics. It was found that the kinetics of the toluene adsorption strongly depends on the position of the substituent groups. Our results showed that the Elovich equation fits the experimental data well for non-peripherally substituted Pc based sensors, while the pseudo first-order model best describes the adsorption data for peripheral substituted Pc based sensors. Some physical, photophysical and photochemical of 2,6-dimethoxyphenoxy substituted metal-free and metallophthalocyanines (indium(III) and zinc(II) Pcs) were investigated by our group [26]. We wondered how copper(II), indium(III), mono-lutetium(III) and tin(IV) Pcs substituted with 2,6-dimethoxyphenoxy bioactive moieties affect the physical, electronic and toluene sensing properties. Hence, highly soluble peripherally and non-peripherally substituted Cu(II), In(III), Lu(III) and Sn(IV) Pcs with 2,6-dimethoxyphenoxy were also synthesized (Scheme 1), and the effects of the position of the substituents and the variety of central metal ions on the their spectroscopic and toluene vapors sensing properties were investigated in this study. KEYWORDS EXPERIMENTAL Materials and Equipment2,6-Dimethoxy-phenoxy substituted phthalonitriles (1 and 2) were obtained by the reaction of 2,6-dimethoxy phenol with 3-nitrophthalonitrile or 4-nitrophthalonitrile through base catalyzed nucleophilic aromatic displacement reaction [26]. All other starting materials and solvents used were obtained commercially. All reactions were carried out under dry nitrogen atmosphere. The novel Pcs (3-10) were successively cleaned by washing with hot acetic acid-water solution by volume 7/3, water, ethanol and acetonitrile in the Soxhlet apparatus. Column chromatography was performed on silica gel 60 for a proper purification of the raw compounds. The purity of the products was tested in each step by thin layer chromotography (Silicagel F-254 coated TLC plate). Melting points of the Pc compounds were found to be higher than 300 °C. IR Spectra and electronic spectra were recorded on a Shimadzu FTIR-8300 (ATR) and a Shimadzu UV-1601 spectrophotometer, respectively. Elemental analyses were performed by the Instrumental Analysis Laboratory of TUBITAK-Ankara. Mass spectra were acquired on a Microflex III MALDI-TOF mass spectrometer (Bruker Daltonics, Germany) equipped with a nitrogen UV-Laser operating at 337 nm in reflectron mode with an average of 50 shots. SynthesisGeneral procedure for the synthesis of metallophth alocyanines (3-10).

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“…Their characteristic B1 and B2 bands (3)(4)(5)(6)(7)(8)(9)(10) were observed at a range of 313-405 nm (Fig. 1).…”

Section: Syntheses and Characterizationmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Toluene vapor sensing characteristics of novel copper(II), indium(III), mono-lutetium(III) and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenoxy bioactive moieties

Pişkin

Can

Odabaş

et al. 2018

J. Porphyrins Phthalocyanines

View full text Add to dashboard Cite

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“…Although many pioneering studies on redox properties, sometimes including spectral changes of porphyrins, have been reported, 17 systematic research on the electrochromic properties including colour changes has not been reported except for a few studies using phthalocyanines. 18–22 Here, we report the colour changes as well as spectroscopic changes of tetraphenylporphyrin (H 2 TPP) and metal complexes (MTPP) upon redox reactions. The metals used are Ag(II), Cu(II), Fe(III), Mg(II), Mn(III), Ni(II) and Zn(II) (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Changes in the absorption spectra and colour of tetraphenylporphyrins after redox reactions

Ogawa

Umetsu

Kamimura

2020

Journal of Chemical Research

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In this study, we have investigated the electrochromic properties including the change in absorption spectra and colour after oxidation and reduction reactions of tetraphenylporphyrin and its metal complexes in dichloromethane. The first oxidation potential is determined from CV measurements, and the reduction potential is estimated from comparison with literature values. Electrolytic reactions are carried out by applying the oxidation potential and reduction potential to each sample solution. The metals used are Ag(II), Cu(II), Fe(III), Mg(II), Mn(III), Ni(II) and Zn(II). Various colours can be expressed after the redox reactions by changing the central metal.

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“…It is advantageous to substitute the functional groups at the peripheral or non-peripheral positions of the Pcs, since they provide solubility and it also tunes the color of the material. Substitution of functional groups also changes the electron density of the phthalocyanines and allows the use in various fields such as solar cells, sensors, liquid crystals, and nonlinear optics (2)(3)(4)(5)(6).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysical properties of usymmetrically substituted phthalocyanine-pyrene conjugate

Karaoğlu

Burat

2019

Journal of the Turkish Chemical Society Section A: Chemistry

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An unsymmetrical zinc phthalocyanine (ZnPc) (5) bearing one pyrene (Py) and six tertbutylphenoxy units was synthesized in 3 steps. The unsymmetrical zinc phthalocyanine carrying the protecting group was synthesized in the first step. In the second stage, the protecting group was removed and in the final stage pyrene structure was introduced with the Sonagashira coupling reaction. The new compound was characterized by using spectroscopic techniques. The photophysical measurements of the conjugated structure were performed to determine the effect of the pyrene group on the fluorescence of Pc. It was determined that the absorption of the pyrene structure around 350 nm was overlapping with the B-band of phthalocyanine after conjugation. Fluorescence quantum yield (ΦF) and lifetime (τF) were calculated. The fluorescence quenching examinations were performed by adding the different concentration of 1,4-benzoquinone (BQ) in N,N-dimethylformamide (DMF) and the Stern-Volmer constant (Ksv) and quenching constant (kq) values of unsymmetrical zinc phthalocyanine (5) were determined.

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Electrochromic Switching of Evaporated Thin Films of Bulky, Electronic Deficient Metallo-Phthalocyanines

Cited by 56 publications

References 36 publications

Toluene vapor sensing characteristics of novel copper(II), indium(III), mono-lutetium(III) and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenoxy bioactive moieties

Toluene vapor sensing characteristics of novel copper(II), indium(III), mono-lutetium(III) and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenoxy bioactive moieties

Changes in the absorption spectra and colour of tetraphenylporphyrins after redox reactions

Synthesis and photophysical properties of usymmetrically substituted phthalocyanine-pyrene conjugate

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