Solid state properties of oligomers containing dithienothiophene or fluorene residues suitable for field effect transistor devices

Porzio, William; Destri, Silvia; Giovanella, Umberto; Pasini, Mariacecilia; Marin, Luminița; Iosip, Mariana Dana; Campione, Marcello

doi:10.1016/j.tsf.2007.02.081

Cited by 24 publications

(11 citation statements)

References 20 publications

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“…[22][23][24][25][26] The design of novel π-conjugated polycyclic cores is therefore the key to improve the performances of liquid-crystalline (LC) semiconductors. In the last decade, LCs based on fused-thiophene subunits have been flourishing, and organic mesogenic derivatives of oligothiophenes, [27][28][29][30][31][32] thienothiophenes (TT), [33,34] dithienothiophenes (DTT), [35][36][37][38][39][40] benzothiophenes (BT), [41][42][43][44] benzotrithiophenes (BTT), [45,46] benzothieno [3,2-b]benzothiophene (BTBT), [47][48][49][50][51][52] materials have been amply reported. Such compounds exhibit high charge mobility with usual rates up to about 10 cm 2 V À 1 s À 1 for a rod-like mesogen [52] and nearly 0.2 cm 2 V À 1 s À 1 for a discotic mesogen, [45] in their highly ordered crystalline phases, directly obtained after annealing from their mesomorphic temperatures and slowly cooled down.…”

Section: Introductionmentioning

confidence: 99%

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Wang

Zhao

et al. 2019

ChemPlusChem

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Board‐like liquid‐crystalline semiconductors based on the dithieno[3,2‐b;2′,3′‐d]thiophene (DTT) substructure were synthesized and their thermal, self‐assembly, optical, and semiconducting properties investigated. These sanidic compounds, bearing eight peripheral chains, are mesomorphic and spontaneously self‐assemble into columnar hexagonal mesophases (Colhex) over broad temperature ranges, as confirmed by polarized optical microscopy, differential scanning calorimetry, and small‐angle X‐ray scattering. Strong blue photoluminescence with absolute quantum yields up to 33 % were measured. These compounds also form blue‐light emitting gels in various organic solvents. The fibrillar‐like morphology of these gels, reminiscent of the columnar structure, and stabilized by efficient intermolecular interactions, was characterized by scanning electron microscopy. The charge carrier mobility of these π‐extended mesogens was measured by time‐of‐flight transient photocurrent technique in the Colhex mesophase, and showed good hole‐transport performance with charge carrier mobility of 10−3 cm2 V−1 s−1.

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Section: Introductionmentioning

confidence: 99%

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Wang

Zhao

et al. 2019

ChemPlusChem

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“…Compared to that of pentacene (−4.96 eV) and other well-known current OFET materials [ 18 ], the lower HOMO energy level of THTP-C suggests that it should have better oxidative stability than traditional p-type semiconductor materials because there would be less probability of oxygen doping [ 7 ]. It is worth noting that such an energy level provides a closer match to the work function of platinum (5.6 eV) for source and drain contacts, which clearly encourages the preparation of prototype p-type OFET devices based on this material [ 19 ]. The LUMO energy level of THTP-C was estimated from the optical band gap and the HOMO energy value [ 17 ].…”

Section: Resultsmentioning

confidence: 99%

A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties

et al. 2011

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FeCl3-mediated oxidative cyclization was successfully used to construct an extended thiophene-pendant pyrene skeleton and synthesize a novel thiophene-fused polycyclic aromatic (THTP-C) with a tetracene core. The identity of the compound was confirmed by 1H-NMR, 13C-NMR, MS, and elemental analysis. Meanwhile, a single crystal of THTP-C was obtained and analyzed by X-ray single-crystal diffraction. THTP-C has a “saddle” shaped π-conjugated 1-D supramolecular structure, and favors highly ordered self-assembly by π-π interactions as evidenced by its concentration-dependent 1H-NMR spectra in solution. The optical properties of THTP-C were investigated by ultraviolet-visible (UV-Vis) and photoluminescence (PL) spectroscopy and its electrochemical properties were investigated by cyclic voltammetry (CV). The relatively large band gap (2.86 eV), low EHOMO level (−5.64 eV) and intermolecular π-π interactions imply that THTP-C has a high stability against photo-degradation and oxidation, and may be a promising candidate for stable hole-transporting materials.

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“…Because of the critical impact of film morphology on electronic device performances,8, 20 the AFM morphological characterization of the treated and untreated film surfaces of the four polymers was considered. Nova v.1443 software was used for recording and analyzing the AFM topographic and phase contrast images.…”

Section: Resultsmentioning

confidence: 99%

Solid state properties of thin films of new copoly(azomethine‐sulfone)s

Marin¹,

Ţîmpu²,

Cozan³

et al. 2010

J of Applied Polymer Sci

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A series of four copoly(azomethine-sulfone)s have been synthesized and extensively characterized. The chemical design has been thought to obtain semiconducting properties and thermotropic behavior matching the processing of the materials from the ordered melted state, suitable for the spontaneous alignment of molecules in the active layer on a substrate. Prototypes of thin films based on this series of polymers have been electrically and structurally characterized. It was found that the respective polymers show typical semiconducting properties. The thermal properties with particular reference to their mesomorphic state were checked by using differential scanning calorimetry, polarized light microscopy, and thermogravimetric analysis techniques. Morphological characterization was realized by atomic force microscopy and X-ray diffraction measurements. Some correlations between electrical properties and packing closeness were established.

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Solid state properties of oligomers containing dithienothiophene or fluorene residues suitable for field effect transistor devices

Cited by 24 publications

References 20 publications

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties

Solid state properties of thin films of new copoly(azomethine‐sulfone)s

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