Solution processible naphthalene and perylene bisimides: Synthesis, electrochemical characterization and application to organic field effect transistors (OFETs) fabrication

Gawryś, Paweł; Boudinet, Damien; Zagórska, Małgorzata; Djurado, David; Verilhac, Jean‐Marie; Horowitz, Gilles; Pécaud, Jacques; Pouget, Stéphanie; Proń, Adam

doi:10.1016/j.synthmet.2009.04.003

Cited by 76 publications

(80 citation statements)

References 38 publications

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“…The growth of modern technology has posed a constantly increasing need for materials that can perform well under harsh conditions, such as elevated temperatures, 4 and processable PIs with special properties have become a subject of great interest all over the world. 5,6 It was found that compounds containing imine rings have prospective applications in organic (opto)electronics and related fields, and that they are exemplary as materials for fabricating field-effect transistors, [6][7][8] organic light-emitting diodes, 9-12 solar cells [12][13][14] and photonic devices. [15][16][17] With regard to the PI microstructure, much effort is being devoted to the design and synthesis of PIs with thioether linkages.…”

Section: Introductionmentioning

confidence: 99%

Physical, optical and gas transport properties of new processable polyimides and poly(amideimide)s obtained from 4,4′-[oxybis(4,1-phenylenethio)]dianiline and aromatic dianhydrides

Grabiec

Schab‐Balcerzak

Wolińska‐Grabczyk

et al. 2011

Polym J

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Aromatic diamine 4,4¢-[oxybis(4,1-phenylenethio)]dianiline and various dianhydrides with isopropylidene, hexafluoroisopropylidene, fluorenylidene diphenyl, ether, thioether and/or amide linkages were applied in a polycondensation reaction to obtain new processable polyimides and poly(amideimide)s (PIs). PIs were synthesized by the conventional two-step procedure of ring-opening polyaddition and subsequent thermal cyclic dehydration. The structures of the polymers were characterized with Fourier-transform infrared spectroscopy and elemental analysis. The thermal behaviors of the PIs were characterized with differential scanning calorimetry, thermogravimetric analysis and dynamic mechanical thermal analysis. The glass transition temperature (T g ) of the PIs were in the range of 175-298 1C and depended on the dianhydride used. The 5% weight loss temperatures were in the range of 423-515 1C, which shows the high thermal resistance characteristics of the PI. The optical absorption properties in the UV-visible range of the obtained polymers were studied in solution and in the solid state. The average refractive indices (n) of the PI films measured at the low absorption range were in the range of 1.96-1.50. The permeation properties of the PIs were studied for He, O 2 , N 2 and CO 2 at 6 atm, with a constant pressure/variable volume setup. The hexafluoroisopropylidene-based PI showed the largest permeability for all gases.

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Section: Introductionmentioning

confidence: 99%

Physical, optical and gas transport properties of new processable polyimides and poly(amideimide)s obtained from 4,4′-[oxybis(4,1-phenylenethio)]dianiline and aromatic dianhydrides

Grabiec

Schab‐Balcerzak

Wolińska‐Grabczyk

et al. 2011

Polym J

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“…Subsequently the newly synthesized monomer (3-7) were introduced in free radical chain growth homopolymerization [20] using THF as solvent and AIBN (Azo bis iso butyronitrile) as initiator to produce the target new polymers (8-12) polymaleimides with pendent bulk Schiff base groups. Physical properties of monomers (3-7) and homopolymers (8)(9)(10)(11)(12) are shown in Tables-1 and 2. It was noticeable that incorporation of bulk pendent group in the new polymers exhibit them good solubility in all organic solvents beside most of them are either gummy products or solids with low softening points and these properties are fitted with the expected ones besides these properties made the polymer suitable for many applications like coating, adhesives , molding and as plasticizers.…”

Section: Al-azzawi and Faiqmentioning

confidence: 99%

“…respectively. Details of FTIR spectral data of homopolymers (8)(9)(10)(11)(12) are listed in Table-4. 1 H-NMR spectrum of homopolymer (10) showed signals at(=1.56)ppm and (3.89)ppm belong to aliphatic protons in imide ring and OCH 3 protons respectively.…”

Section: Table 3-ftir Spectral Data (Cm -1 ) Of Schiff Bases (3-7)mentioning

confidence: 99%

“…Many efforts have been made to solve these problems since developing these properties can be an important approach to their use in many new fields [7][8][9][10][11][12][13]. Thus in the present work we try to improve polymaleimides properties by two ways the first one involved introducing of bulk Schiff base moieties as pendant groups in polymeric chains of polymaleimides ,while the second way involved introducing of maleimides substituted with Schiff bases into copolymerization with acrylonitrile since copolymerization is the most efficient method for modifying polymer properties [14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Polymerization of Several New Maleimides Linked to Schiff Bases and Their Copolymers with Acrylonitrile

2017

ijs

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A series of new maleimide monomers substituted with Schiff base moieties were synthesized via acid-catalyzed condensation of 3-(N-maleimidyl)phenyl hydrazide with aromatic aldehydes and ketones. The newly synthesized monomers were introduced in free radical chain growth homopolymerization producing five new polymaleimides with pendent Schiff base moieties .The new monomers were introduced also in free radical chain growth copolymerization with acrylonitrile producing new five copolymaleimides containing pendent Schiff base moieties. The new homopolymers and copolymers are of great importance since incorporation of bulky Schiff base moieties in their repeating units exhibit them better solubility and processing properties which made them suitable for a variety of important applications.

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“…Although the electron mobility of NDI has obvious decreased, the nitrogen atoms of NDI could be substituted by alkyls or other groups affording us versatile ways to obtain solution-processable n-type semiconductors with different electronic properties. Indeed, a lot of alkyls or other groups substituting NDIs exhibited high electron mobility [293][294][295][296]. For example, the hexyl-substituted NDI, 240b showed a high electron mobility up to 0.7 cm 2 V −1 s −1 .…”

Section: Diimidesmentioning

confidence: 99%

Organic Semiconductors for Field-Effect Transistors

Zhang

2015

Lecture Notes in Chemistry

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An important application of organic semiconductors is to fabricate organic field-effect transistors (OFETs) which are essential building blocks for the next generation of organic circuits. In terms of molecular size or molecular weight, organic semiconductors can be divided into small-molecule and polymer semiconductors, and thus their corresponding OFETs can also be categorized into organic small molecule OFETs and polymer field-effect transistors (PFETs). On the basis of the main charge carriers transporting in OFET channels, organic semiconductors can be further divided into p-type, n-type, and ambipolar semiconducting materials. According to the characteristic of the organic semiconductors, the OFETs can be classified into two types: organic thin film transistors (OTFTs) and organic single crystal transistors. In any kind of OFET devices, organic semiconductor materials are the core; their properties determine the performance of the electronic devices. Therefore, the design and synthesis of high performance organic semiconductor materials are the basis and premise of the wide application of OFET devices. In the past few decades, great progress has been made in developing organic semiconductors. Besides organic semiconducting materials, there are many other factors influencing the performance of OFETs including device configuration, processing technique, and other devices physical factors, etc. In the following, a brief review of the development of p-type, n-type, ambipolar organic semiconductors and their field-effect properties is given. The history, mechanism, configuration, and fabrication methods of OFET devices and main performance influencing factors of OFETs are also introduced.

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Solution processible naphthalene and perylene bisimides: Synthesis, electrochemical characterization and application to organic field effect transistors (OFETs) fabrication

Cited by 76 publications

References 38 publications

Physical, optical and gas transport properties of new processable polyimides and poly(amideimide)s obtained from 4,4′-[oxybis(4,1-phenylenethio)]dianiline and aromatic dianhydrides

Physical, optical and gas transport properties of new processable polyimides and poly(amideimide)s obtained from 4,4′-[oxybis(4,1-phenylenethio)]dianiline and aromatic dianhydrides

Synthesis and Polymerization of Several New Maleimides Linked to Schiff Bases and Their Copolymers with Acrylonitrile

Organic Semiconductors for Field-Effect Transistors

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