Phenyl- and Thienyl-Ended Symmetric Azomethines and Azines as Model Compounds for n-Channel Organic Field-Effect Transistors: An Electrochemical and Computational Study

Vercelli, Barbara; Pasini, Mariacecilia; Berlin, Anna; Casado, Juan; Navarrete, Juan T. López; Ortiz, Rocío Ponce; Zotti, Gianni

doi:10.1021/jp411815w

Cited by 31 publications

(25 citation statements)

References 41 publications

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“…The radical anions generated in the course of the CV experiment are unstable and are easily protonated owing to their high basicity. A similar shift to the anodic region was observed previously for azines with aryl and heterocyclic substituents , …”

Section: Resultssupporting

confidence: 86%

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

et al. 2016

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The ferrocenyl‐containing 3,5‐di‐tert‐butylcatechol Fc‐L‐CatH2 (2) was synthesized by the condensation of the precursor 6‐(hydrazonomethyl)‐3,5‐di‐tert‐butylcatechol 6‐(H2N–N=CH)CatH2 (1) with ferrocenecarboxaldehyde (L = –CH=N–N=CH–, Cat = 3,5‐di‐tert‐butylcatecholate, Fc = ferrocene). The exchange reaction between catechol 2 and Ph3SbBr2 in the presence of a base (Et3N) in toluene leads to the formation of the triphenylantimony(V) catecholate (Fc‐L‐Cat)SbPh3 (3) as the main product and the ionic bromotriphenylantimony(V) catecholate (Fc‐LH‐Cat)SbPh3Br (4) containing a hydraziniumylidene cation (LH = –CH=NH+–N=CH–) as the byproduct. The change of toluene to tetrahydrofuran (THF) results in the formation of 4 as the main product in nearly quantitative yield. The exchange reactions of catechol 2 with Ph2SnCl2 and SnCl4 give anionic catecholate complexes bridged with hydraziniumylidene cations even in the presence of excess base. Complexes (Fc‐LH‐Cat)SnPh2Cl (5), (Fc‐LH‐Cat)2SnPh2 (6), and (Fc‐LH‐Cat)2SnCl2 (7) were synthesized. The compounds obtained were characterized by IR spectroscopy, 1H and 13C NMR spectroscopy, elemental analysis, and cyclic voltammetry. The molecular structures of crystals of 5–7 were determined by X‐ray diffraction analysis. The formation of catecholates 4–7 with hydraziniumylidene cations is caused by intramolecular hydrogen bonding between the hydroxy and imine groups, which leads to proton transfer from the oxygen atom to the nitrogen atom of the hydrazine linker.

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Section: Resultssupporting

confidence: 86%

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

et al. 2016

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“…The HOMO and LUMO levels of P1 , P2 , and P3 were obtained from the onsets of the oxidation and reduction potential [ 44 ], respectively, and are reported in Table 1 together with UV−vis spectroscopic data. The deviation between the optical and electrochemical results are in quite satisfactory agreement, as previously described in literature [ 45 ].…”

Section: Resultssupporting

confidence: 89%

Sulfonate-Conjugated Polyelectrolytes as Anode Interfacial Layers in Inverted Organic Solar Cells

et al. 2021

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Conjugated polymers with ionic pendant groups (CPEs) are receiving increasing attention as solution-processed interfacial materials for organic solar cells (OSCs). Various anionic CPEs have been successfully used, on top of ITO (Indium Tin Oxide) electrodes, as solution-processed anode interlayers (AILs) for conventional devices with direct geometry. However, the development of CPE AILs for OSC devices with inverted geometry is an important topic that still needs to be addressed. Here, we have designed three anionic CPEs bearing alkyl-potassium-sulfonate side chains. Their functional behavior as anode interlayers has been investigated in P3HT:PC61BM (poly(3-hexylthiophene): [6,6]-phenyl C61 butyric acid methyl ester) devices with an inverted geometry, using a hole collecting silver electrode evaporated on top. Our results reveal that to obtain effective anode modification, the CPEs’ conjugated backbone has to be tailored to grant self-doping and to have a good energy-level match with the photoactive layer. Furthermore, the sulfonate moieties not only ensure the solubility in polar orthogonal solvents, induce self-doping via a right choice of the conjugated backbone, but also play a role in the gaining of hole selectivity of the top silver electrode.

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“…They have many intrinsic advantages, i.e., well-elucidated molecular structures, molecular weights, high purity, and good charge-carrier mobility. 1−5 The performance of OFETs mainly depends on the structural characteristics of the active semiconducting material as well as the processing method employed during thin-film fabrication. 24 To reduce the fabrication cost for large-area manufacturing, implementation of solution process techniques like spin coating, blade coating, and inkjet printing are more favorable compared to vacuum deposition methods.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optoelectrical Characterization of Novel Squaraine Dyes Derived from Benzothiophene and Benzofuran

et al. 2018

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Synthesis and photophysical characterizations of two novel small molecules SQ-BEN-THI and SQ-BEN-FUR with D–A–D molecular structure consisting of squaraine as central unit and benzothiophene and benzofuran as end groups are being reported. Apart from very sharp and intense light absorption by these molecular sensitizers in near-infrared (NIR) wavelength region, their possibility as small molecular organic semiconductor was also explored after fabricating organic field-effect transistors (OFETs). Results obtained from photophysical, electrochemical, and quantum chemical studies were combined to elucidate the structural and optoelectronic properties. Electrical characterization pertaining to the charge-transport properties carried after OFET fabrication exhibited field-effect mobilities of 4.0 × 10 –5 and 5.4 × 10 –5 cm 2 /(V s) for SQ-BEN-THI and SQ-BEN-FUR , respectively. After thermal annealing at 130 °C, the field-effect mobility was found to increase for both squaraine dyes. Relatively facile carrier transport in SQ-BEN-FUR compared to that of SQ-BEN-THI could be attributed to relatively higher backbone planarity as indicated from optimized molecular structure obtained after density functional theory calculations. This work may guide for further molecular design and synthesis of novel squaraine dyes for high-performance OFET applications.

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Phenyl- and Thienyl-Ended Symmetric Azomethines and Azines as Model Compounds for n-Channel Organic Field-Effect Transistors: An Electrochemical and Computational Study

Cited by 31 publications

References 41 publications

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

Sulfonate-Conjugated Polyelectrolytes as Anode Interfacial Layers in Inverted Organic Solar Cells

Synthesis and Optoelectrical Characterization of Novel Squaraine Dyes Derived from Benzothiophene and Benzofuran

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