Effect of substituents on the orientation of octasubstituted copper(II) phthalocyanine thin films

Basova, Tamara; Çamur, Meryem; Esenpınar, Aliye Aslı; Tuncel, Sinem; Hassan, Aseel; Alexeyev, A. V.; Banimuslem, Hikmat; Durmuş, Mahmut; Gürek, Ayşe Gül; Ahsen, Vefa

doi:10.1016/j.synthmet.2012.02.006

Cited by 24 publications

(18 citation statements)

References 52 publications

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“…The conductivities of 4a-f films deposited onto the interdigitated electrode structures were measured in the direction parallel to the films plane; the results are summarized in Table 3. The lateral conductivity tends to decrease with the increase of chain length (films 4a and 4b; 4c and 4d) similar to the films of phthalocyanine molecules described by other researchers [17,47].…”

Section: Comparative Study Of the Sensor Properties Of Cupc Filmssupporting

confidence: 82%

“…It is interesting to mention that the 4c, 4e and 4f derivatives tend to form ordered films with the cofacial arrangement of phthalocyanine macrocycles even without heating. This type of ordering is similar to that of the films of octaalkyl analogues which also form Col mesophases [17,42]. and 4b consist of small elongated aggregates.…”

Section: Films Characterizationsupporting

confidence: 70%

“…Table 4. The symmetry types of vibrations were assigned by analogy with similar phthalocyanine molecules [17,44] [45,46].…”

Section: Films Characterizationmentioning

confidence: 99%

“…In a previous study [17] we have addressed the liquid crystalline behavior of octasubstituted phthalocyanine derivatives (CuPcR 8 ) substituted with alkylthio-, alkyloxy-, (trioxyethylene)thio-and (trioxyethylene)oxy-substituents in peripheral positions over a wide range of temperatures. The significant dependence of crystal-to-mesophase and mesophase-toisotropic phase transition temperatures on the number of alkyl substituents was revealed for these phthalocyanines [17]. It was also known that both the mesophase type and the transition temperature also depend on the length of the alkyl chains [18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

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Tetrasubstituted copper phthalocyanines: Correlation between liquid crystalline properties, films alignment and sensing properties

Gülmez

Polyakov

Volchek

et al. 2017

Sensors and Actuators B: Chemical

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Copper phthalocyanines (CuPc) containing alkylthio (-S(CH 2) n CH 3 , n=7 and 15), alkyloxy-(-O(CH 2) n CH 3 , n=7 and 15) and polyoxo (-O(CH 2 CH 2 O) 3 CH 3 and-S(CH 2 CH 2 O) 3 CH 3) substituents were synthesized and investigated to reveal the effects of substituents type (alkylthio, alkyloxy and polyoxo) and the type of the connecting heteroatom (oxygen or sulphur) on the mesogenic properties, films alignment and sensing behaviour. The liquid crystalline properties of these phthalocyanines were investigated by differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction techniques. The structure and morphology of spun thin films of copper phthalocyanine derivatives were studied by the UV-Vis and Raman spectroscopies as well atomic force microscopy. The sensing properties of CuPc films were studied by the measurement of conductivity change upon interaction with ammonia in the range 10-50 ppm. All investigated films of CuPc derivatives display thermotropic columnar mesomorphism. It was shown that the films with polyoxo-(-O(CH 2 CH 2 O) 3 CH 3 and-S(CH 2 CH 2 O) 3 CH 3) substituents as well as with alkylthio-S(CH 2) n CH 3 (n=7) substituents, which are liquid crystalline at room temperature, form ordered films with a random planar alignment of columns. Their films exhibit the better sensor performance with the maximal sensor response for the films of CuPc containing (-S(CH 2 CH 2 O) 3 CH 3) substituents.

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Section: Comparative Study Of the Sensor Properties Of Cupc Filmssupporting

confidence: 82%

Section: Films Characterizationsupporting

confidence: 70%

“…Table 4. The symmetry types of vibrations were assigned by analogy with similar phthalocyanine molecules [17,44] [45,46].…”

Section: Films Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Tetrasubstituted copper phthalocyanines: Correlation between liquid crystalline properties, films alignment and sensing properties

Gülmez

Polyakov

Volchek

et al. 2017

Sensors and Actuators B: Chemical

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“…However, these structural modifications can promote, in some cases, a significant decrease in their planarity. 5 A simple way to obtain porphyrins is the acid catalyzed condensation reaction of pyrrole with specific aldehyde, followed by oxidation of the porphyrinogen. This procedure, originally developed by Rothemund,6 has been refined by Adler-Longo, [7][8][9] due to the addition of metal salts to the reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Mota¹,

Júnior²,

Ribeiro³

et al. 2016

J. Braz. Chem. Soc.

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New asymmetric cardanol-based porphyrins, free-base and coordinated with Ni, Co and Cu, were synthesized and completely characterized as A3B type. Such porphyrins were obtained aiming improved solubility in polar solvents due insertion of an −OH phenolic group. Their thermal and dielectric properties were also evaluated. Changes in the synthetic route reduced the reaction time and improved the yields of the aldehyde precursor obtainment. Electronic absorption spectra of the new porphyrins in CH 2 Cl 2 , EtOH and acetone, indicated a decrease in the ε (molar absorptivity) values with increasing solvent polarity, except for the nickel complex which, in acetone, showed a slight increase of 2% in the ε value. The dielectric measurements showed that the conductivity (σ) and the loss tangent (tan δ) increased with frequency, but the permittivity (ε') decreased. The results showed that the coordination of the porphyrin promoted a significant change in thermal and dielectric properties, specially for to the Ni-complex compound, which presented the best dielectric properties with interesting values of permittivity and loss tangent at 100 MHz (19.46 and 0.011 a.u., respectively). Keywords: asymmetric porphyrins, cardanol, dielectric properties IntroductionPorphyrins are relatively planar aromatic system consisting of four pyrrole type rings joined by four methynic carbons. They have attracted scientists from many areas due to their biological importance, their fascinating physical, chemical, and spectroscopic properties.1 These compounds have a high electron density due to its 18 π-electrons delocalized on the macrocyclic ring, which are responsible for their spectroscopic characteristics. 2Porphyrin and its derivatives play multiple roles in nature, such as energy transfer and light absorption in a wide range of the electromagnetic spectrum. Such features are of great interest to the industry of optoelectronic components, such as solar cells, due to its ability to act as photosensitizers when irradiated under visible light.3 Thus, this is certainly one of the most promising areas of application for these compounds. The structural modeling and synthesis of new porphyrins has grown exponentially in order to control their electronic and thermal properties. 4 The addition of substituents at the meso positions and metal ions in the center of porphyrins can improve the electrical and magnetic properties, protecting against auto-oxidation and reducing the formation of dimers. However, these structural modifications can promote, in some cases, a significant decrease in their planarity. 5A simple way to obtain porphyrins is the acid catalyzed condensation reaction of pyrrole with specific aldehyde, followed by oxidation of the porphyrinogen. This procedure, originally developed by Rothemund,6 has been refined by [7][8][9] due to the addition of metal salts to the reaction. Despite the modest yields, the relative simplicity of this method has become suited for preparation of large amounts of tetraarylporphyrins. Higher yields an...

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An electrochemically prepared sky-blue light emitting ether functionalized polyfluorene as chemosensor for metal ions

et al. 2013

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Effect of substituents on the orientation of octasubstituted copper(II) phthalocyanine thin films

Cited by 24 publications

References 52 publications

Tetrasubstituted copper phthalocyanines: Correlation between liquid crystalline properties, films alignment and sensing properties

Tetrasubstituted copper phthalocyanines: Correlation between liquid crystalline properties, films alignment and sensing properties

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

An electrochemically prepared sky-blue light emitting ether functionalized polyfluorene as chemosensor for metal ions

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