Crystalline Mono‐ and Multilayer Self‐Assemblies of Oligothiophenes at the Air–Water Interface

Isz, Sandrine; Weissbuch, Isabelle; Kjær, Kristian; Bouwman, Wim G.; Als‐Nielsen, J.; Ruaudel‐Teixier, A.; Leiserowitz, Leslie; Lahav, Meir

doi:10.1002/chem.19970030615

Cited by 15 publications

(15 citation statements)

References 25 publications

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“…In recent years, quantum dots were prepared mainly in matrices and also as self-assembled structures, such as reverse micelles, [10] zeolites, [11] polymers, [12] self-assembled monolayers, [13] biopolymers, [14] layered metal phosphonates, [15] and Langmuir±Blodgett (LB) films. [16,17] In the preceding communication, [18] we reported that spreading of tetracosanedioic acid HOOC(CH 2 ) 22 COOH (C 24 diacid) on surfaces of aqueous solutions containing di- …”

Section: Methodsmentioning

confidence: 98%

“…Recently, the formation at the air±water interface of crystalline monolayer and multilayer films obtained from symmetric molecules with end groups equally hydrophobic or hydrophilic, such as long-chain linear fluorocarbons [14] and hydrocarbons, [15] oligothiophenes [16] (containing four, five, and six rings), and a,w-alkanediols, [17] has been reported. In these films at low surface pressure the long molecular axis is aligned either normal to the water surface or tilted by up to 40 from the normal.…”

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confidence: 99%

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Oriented Crystalline Thin Films of Tetracosanedioic Acid and Its Metal Salts at the Air-Aqueous Solution Interface

Weissbuch¹,

Guo

Edgar

et al. 1998

Adv. Mater.

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Langmuir monolayers are conventionally prepared by spreading, on a water surface, amphiphilic molecules containing hydrophilic head groups, which interact with the water molecules, and hydrophobic chains, which favor lateral aggregation in air. The crystalline packing of the molecules in the monolayer has been determined in situ, with almost atomic resolution by means of synchrotron X-ray diffraction using a monochromatic beam at grazing incidence.[1] With the use of this technique, the two-dimensional crystalline packing arrangement of monolayers of long-chain alcohols, [2±4] carboxylic acids, [5,6] amides, [7] aamino acids, [8±10] and phospholipids [11±13] could be determined. Recently, the formation at the air±water interface of crystalline monolayer and multilayer films obtained from symmetric molecules with end groups equally hydrophobic or hydrophilic, such as long-chain linear fluorocarbons [14] and hydrocarbons, [15] oligothiophenes [16] (containing four, five, and six rings), and a,w-alkanediols, [17] has been reported. In these films at low surface pressure the long molecular axis is aligned either normal to the water surface or tilted by up to 40 from the normal. Moreover, the formation of crystalline interdigitated trilayers from water-insoluble long-chain mandelic acid and phenylethylamine molecules contained in the subphase was proven by grazing incidence X-ray diffraction (GID).[18]The changes in packing arrangement of monolayers composed of long-chain carboxylic acids, as induced by the presence in the subphase of Cd 2+ , Ca 2+ , or Pb 2+ ions, have also been determined by GID. Over pure water and in the uncompressed state, the chains are tilted by approximately 30 from the normal to the water surface, whereas over solutions containing the metal ions, the chains are vertically aligned. [19,20] This report describes the self-assembly process of a,wtetracosanedioic acid, HOOC±(CH 2 ) 22 ±COOH, on aqueous subphases containing divalent Cd 2+ and Pb 2+ ions.These positive ions have a dramatic influence on the packing of the diacid molecules: they bind to both carboxylate ends of the molecule and force the long hydrocarbon chain to lie parallel to the water surface and to self-assemble as multilayer domains about 50 thick, but with the molecules and the bound ions perfectly ordered laterally over distances up to 1000 . GID and specular X-ray reflectivity (XR) were used to characterize the oriented crystalline multilayers of these cadmium and lead salts. Such multilayer films preserve their orientation during the transfer from the water surface onto a mica support, as imaged by scanning force microscopy (SFM), and can be used in the preparation of quantum dots (see following communication [21] ).The GID experiments were carried out at the synchrotron beamline BW1, HASYLAB, on the liquid surface diffractometer, as described elsewhere.[1] The samples were prepared by spreading solutions of the diacid onto pure water and onto aqueous subphases containing the metal ions, at 15 C, to give a nominal molecul...

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Section: Methodsmentioning

confidence: 98%

mentioning

confidence: 99%

Oriented Crystalline Thin Films of Tetracosanedioic Acid and Its Metal Salts at the Air-Aqueous Solution Interface

Weissbuch¹,

Guo

Edgar

et al. 1998

Adv. Mater.

Self Cite

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“…Charge carriers are trapped or scattered by defects and impurities in the accumulation region or at its interfaces. In addition, at such small thicknesses, due to the small size of the crystal and the proximity of the gate insulator interfaces, monolayers of small‐molecule organic semiconductors have a complex arrangement of molecules, often including different island morphologies and crystallographic structures than in thicker films 7, 8. The crystallographic differences lead to different intrinsic overlap of the molecular orbitals of adjacent molecules and thus to different hole transport characteristics 9.…”

Section: Introductionmentioning

confidence: 99%

High Hole Mobility and Thickness‐Dependent Crystal Structure in α,ω‐Dihexylsexithiophene Single‐Monolayer Field‐Effect Transistors

Mannebach

Spalenka

Johnson

et al. 2012

Adv Funct Materials

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Monolayer‐thickness two‐dimensional layers of α,ω‐dihexylsexithiophene (α,ω‐DH6T) exhibit field‐effect hole mobility of up to 0.032 cm2 V−1 s−1, higher than previously reported for monolayers of other small‐molecule organic semiconductors. In situ measurements during deposition show that the source‐drain current saturates rapidly after the percolation of monolayer‐high islands, indicating that the electrical properties of α,ω‐DH6T transistors are largely determined by the first molecular monolayer. The α,ω‐DH6T monolayer consists of crystalline islands in which the long axes of molecules are oriented approximately perpendicular to the plane of the substrate surface. In‐plane lattice constants measured using synchrotron grazing‐incidence diffraction are larger in monolayer‐thickness films than the in‐plane lattice constants of several‐monolayer films and of previously reported thick‐film structures. Near‐edge X‐ray absorption fine structure spectroscopy (NEXAFS) reveals that the larger in‐plane lattice constant of single‐monolayer films arises from a larger tilt of the molecular axis away from the surface normal. NEXAFS spectra at the C 1s and S 2p edges are consistent with a high degree of molecular alignment and with the local symmetry imposed by the thiophene ring. The high mobility of holes in α,ω‐DH6T monolayers can be attributed to the reduction of hole scattering associated with the isolation of the thiophene core from the interface by terminal hexyl chains.

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“…The hydrophobic Ni 3 (HITP) 2 nanoparticles float on the water surface, which acts as a “smooth substrate”, and consequently the nanoparticles closely pack to form a nanometer-thick uniform layer due to the interface-confining effect (Figure S1). , After the air–liquid interface is fully covered with this Ni 3 (HITP) 2 layer, the MOF membrane probably forms through continuous assembly of organic HITP components and nickel ions in the solution onto the Ni 3 (HITP) 2 layer at the MOF–solution interface. The formation of the membrane at the interface could be observed even by the naked eye.…”

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confidence: 99%

“…Herein we demonstrate an air−liquid interfacial method to prepare ultrasmooth and compact Ni 3 (HITP) 2 membranes S1). 20,21 After the air−liquid interface is fully covered with this Ni 3 (HITP) 2 layer, the MOF membrane probably forms through continuous assembly of organic HITP components and nickel ions in the solution onto the Ni 3 (HITP) 2 layer at the MOF−solution interface. The formation of the membrane at the interface could be observed even by the naked eye.…”

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confidence: 99%

Porous Field-Effect Transistors Based on a Semiconductive Metal–Organic Framework

et al. 2016

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Recently, the emergence of conductive metal-organic frameworks (MOFs) has given great prospects for their applications as active materials in electronic devices. In this work, a high-quality, free-standing conductive MOF membrane was prepared by an air-liquid interfacial growth method. Accordingly, field-effect transistors (FETs) possessing a crystalline microporous MOF channel layer were successfully fabricated for the first time. The porous FETs exhibited p-type behavior, distinguishable on/off ratios, and excellent field-effect hole mobilities as high as 48.6 cm V s, which is even comparable to the highest value reported for solution-processed organic or inorganic FETs.

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Crystalline Mono‐ and Multilayer Self‐Assemblies of Oligothiophenes at the Air–Water Interface

Cited by 15 publications

References 25 publications

Oriented Crystalline Thin Films of Tetracosanedioic Acid and Its Metal Salts at the Air-Aqueous Solution Interface

Oriented Crystalline Thin Films of Tetracosanedioic Acid and Its Metal Salts at the Air-Aqueous Solution Interface

High Hole Mobility and Thickness‐Dependent Crystal Structure in α,ω‐Dihexylsexithiophene Single‐Monolayer Field‐Effect Transistors

Porous Field-Effect Transistors Based on a Semiconductive Metal–Organic Framework

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