Molecular orientation and electrical behaviour of Langmuir-Blodgett films of phthalocyanine derivatives containing eight alkyl chains

Nakahara, Hiroyuki; Sun, Kai; Fukuda, Kiyoshige; Azuma, Natsuhiro; Nishi, Hisao; Uchida, Hidekazu; Katsube, Teruaki

doi:10.1039/jm9950500395

Cited by 20 publications

(6 citation statements)

References 10 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%

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%

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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“…184,185 In other cases, the introduction of hydrogen bonds leads to a face-on orientation with the discs ''lying flat'' on the water surface and the hydrocarbon chains extending away from the water interface. 186,187 This obviously precludes the formation of the desired uniaxial alignment.…”

Section: Homeotropic Alignmentmentioning

confidence: 99%

Discotic liquid crystals: a new generation of organic semiconductors

2007

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Discotic (disc-like) molecules typically comprising a rigid aromatic core and flexible peripheral chains have been attracting growing interest because of their fundamental importance as model systems for the study of charge and energy transport and due to the possibilities of their application in organic electronic devices. This critical review covers various aspects of recent research on discotic liquid crystals, in particular, molecular design concepts, supramolecular structure, processing into ordered thin films and fabrication of electronic devices. The chemical structure of the conjugated core of discotic molecules governs, to a large extent, their intramolecular electronic properties. Variation of the peripheral flexible chains and of the aromatic core is decisive for the tuning of self-assembly in solution and in bulk. Supramolecular organization of discotic molecules can be effectively controlled by the choice of the processing methods. In particular, approaches to obtain suitable macroscopic orientations of columnar superstructures on surfaces, that is, planar uniaxial or homeotropic alignment, are discussed together with appropriate processing techniques. Finally, an overview of charge transport in discotic materials and their application in optoelectronic devices is given.

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“…2,11,12 The relationship between the physical properties of Pc films and the molecular orientation was widely investigated in recent years by employing different experimental techniques. 9,10,13,14 Sandwich-type phthalocyaninato double deckers, in which the large conjugated π systems are held in close proximity by rare-earth ions, have attracted great attention because of their application in organic materials science. 15,16 These types of molecules have recently been found to be good candidates for potential applications in the fields of molecular electronics, molecular optronics, and molecular iono-electronics.…”

Section: Introductionmentioning

confidence: 99%

“…The columnar architecture of the mesophase suggests the possibility of using them as anisotropic conductors 4c. Since the discovery of mesogenity, a variety of mesogenic Pcs have been prepared. , The application potential of Pc films heavily depends on the ability to prepare them in thin films by vacuum deposition, organic molecular beam epitaxy, , and Langmuir−Blodgett film formation. , Spin-coating technology has also been demonstrated as a useful method of preparing oriented Pc films. ,, The relationship between the physical properties of Pc films and the molecular orientation was widely investigated in recent years by employing different experimental techniques. ,,, …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Spectroscopic and Magnetic Properties of Mesomorphic Octakis(hexylthio)-Substituted Phthalocyanine Rare-Earth Metal Sandwich Complexes

et al. 2006

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The syntheses of new bis[octakis(hexylthio)phthalocyaninato] rare-earth metal(III) double-decker complexes [(C6S)8-Pc]2M (M = Gd(III), Dy(III), and Sm(III)) (2-4, respectively) are described. These compounds are very soluble in most common organic solvents. They have been fully characterized using elemental analysis, infrared, UV-vis spectroscopy, and mass spectrometry. The crystal structures of compounds 2-4 have been determined by X-ray diffraction on a single crystal. They are isostructural and crystallize in the monoclinic space group (space group C2/c). Their lattice constants have been determined in the following order: (2) a = 31.629(4) Angstroms, b = 32.861(4) Angstroms, c = 20.482(2) Angstroms, beta = 126.922(2) degrees, V = 17019(3) Angstroms(3); (3) a = 31.595(2) Angstroms, b = 32.816(2) Angstroms, c = 20.481(1) Angstroms, beta = 127.005(1) degrees, V = 16958(2) Angstroms(3); (4) a = 31.563(2) Angstroms, b = 32.796(2) Angstroms, c = 20.481(1) Angstroms, beta = 127.032 degrees, V = 16924(2) Angstroms(3). The magnetic properties of compounds 2-4 were studied, and it was revealed that the lanthanide ions and the radical delocalized on the two phthalocyanine rings are weakly interacting. The mesogenic properties of these new materials were studied by differential scanning calorimetry and optical microscopy. These phthalocyanine derivatives form columnar-hexagonal (Col(h)) mesophases. Thin films of bis[octakis(hexylthio)phthalocyaninato] rare-earth metal(III) double-decker complexes (2-4) were prepared by a spin-coating technique. Thermally induced molecular reorganization within films of bis[octakis(hexylthio)phthalocyaninato] rare-earth metal(III) double-decker complexes (2-4) was studied by the methods of ellipsometry, UV-vis absorption spectroscopy, and atomic force microscopy. Heat treatment produces molecular ordering, which is believed to be due to stacking interaction between neighboring phthalocyanine moieties.

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Molecular orientation and electrical behaviour of Langmuir-Blodgett films of phthalocyanine derivatives containing eight alkyl chains

Cited by 20 publications

References 10 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

Discotic liquid crystals: a new generation of organic semiconductors

Synthesis, Structure, and Spectroscopic and Magnetic Properties of Mesomorphic Octakis(hexylthio)-Substituted Phthalocyanine Rare-Earth Metal Sandwich Complexes

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