Synthesis of novel azo-bridged phthalocyanines and their toluene vapour sensing properties

Şahin, Safinaz; Altun, Selçuk; Altındal, Ahmet; Odabaş, Zafer

doi:10.1016/j.snb.2014.09.110

Cited by 44 publications

(18 citation statements)

References 33 publications

(38 reference statements)

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“…2 clearly shows that the interaction of the toluene vapor with the sensor surface causes an unexpected increase in sensor current. Although this finding is in agreement with the earlier toluene sensing studies of CuPc Langmuir-Blodgett film [32,33], the increase in the conductivity of the sensor in toluene vapor ambient is an unexpected behavior. Figure 2 also shows that the response-recovery characteristics of the sensors are very regular without any drift in baseline current.…”

Section: Toluene Sensingsupporting

confidence: 91%

“…Very good correlation coefficients for compounds 4, 6, 8, and 10, when compared with 3, 5, 7, and 9, indicate that the adsorption of toluene vapors onto the nonperipherally 2,6-dimethoxyphenol substituted Pcs was more favorable by the pseudo-second order kinetic model. In our previous work, we studied the effect of relative humidity and bridging units on the toluene vapor detection capabilities of novel dimethoxyphenoxy phthalocyanine thin films [33]. We found that the toluene sensitivity of the films strongly depends on the bridging unit: toluene sensitivities of the azo-bridged Pcs were higher than those of the homologous oxobridged derivatives.…”

Section: The First-order Modelmentioning

confidence: 98%

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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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Section: Toluene Sensingsupporting

confidence: 91%

Section: The First-order Modelmentioning

confidence: 98%

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

Self Cite

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“…Although the interaction of gas molecules with the film surface was a complicated phenomenon, central metal atom and the substituent effect had also a vital role for determination of different gas sensing features such as toluene. [41,42] In addition, introduction of electron donating or withdrawing substituents to Pc macrocycles led to change in the sensitivity of MPcs to various analytes since modifications of the electronic distribution, and the molecule energetic levels were present in the aromatic macrocycle. [43] Electron-withdrawing iodine substituents may also reduce electron density of the aromatic macrocycle and increase the oxidation potential of the molecule, which improves sensitivity of the iodosubstituted Pcs to NH 3 .…”

Section: Qcm Gas Adsorption Studiesmentioning

confidence: 99%

Investigation of electrochemical properties and gas adsorption studies of novel sandwich core phthalocyanines

Şenocak

Köksoy

Demirbaş

et al. 2018

J of Physical Organic Chem

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In this study, bis(tetra-iodo-phthalocyanine)s containing different lanthanide (III) metals, namely, samarium (III) (SmPc 2 ), europium (III) (EuPc 2 ), gadolinium (III) (GdPc 2 ), dysprosium (III) (DyPc 2 ), and terbium (III) (TbPc 2 ) were synthesized for the first time, and their structural characterizations were determined by elemental analyses and different spectroscopic methods such as Ultraviolet-Visible (UV-Vis), Fourier transform infrared (FT-IR), and matrix-assisted laser desorption/ionization-time of flight (MALDI-TOF). Moreover, voltammetric, in situ spectroelectrochemical, chemical redox, and quartz crystal microbalance (QCM) gas adsorption properties of the synthesized compounds were evaluated. The distinct spectral and color changes during the redox reactions for the complexes indicated a potential use in electrochromic materials. In addition, ammonia gas adsorption properties of the complexes were found to be relevant to central metal atom size, and the value for the ammonia gas adsorption at 15 μg/L was the highest for SmPc 2 (20 ng), and the lowest was DyPc 2 (1.4 ng).

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“…The phthalocyanine (Pc) molecules are belong in the organic semiconductors which offer significant potential for the fundamental and applied sciences. The Pc distinguish itself as one from the most stabilized organic materials which show no remarkable degradation beneath air exposure, its temperature stabilization up to the about 400•C [4], that has excellent stabilization against light, heat, oxygen and moisture, cost low, have good selectivity and sensitivity [5], chemical and thermal stability, and as well catalytic [6]. And possibility of tune those properties by insert various metals to macrocycles central bore or by introduce different substituents in their rings peripheries [7].…”

Section: Introductionmentioning

confidence: 99%

Effects of central aluminum on spectroscopic properties of hexadeca fluorinated phthalocyanine

Ibrahim¹,

Ghaleb²,

Mohammed³

2019

astp

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Synthesis of novel azo-bridged phthalocyanines and their toluene vapour sensing properties

Cited by 44 publications

References 33 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

Investigation of electrochemical properties and gas adsorption studies of novel sandwich core phthalocyanines

Effects of central aluminum on spectroscopic properties of hexadeca fluorinated phthalocyanine

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