Charge transfer complexes of a benzothienobenzothiophene derivative and their implementation as active layer in solution-processed thin film organic field-effect transistors

Fijahi, Lamiaa; Salzillo, Tommaso; Tamayo, Adrián; Bardini, Marco; Ruzié, Christian; Quarti, Claudio; Beljonne, David; D’Agostino, Simone; Geerts, Yves; Mas‐Torrent, Marta

doi:10.1039/d2tc00655c

Cited by 12 publications

(18 citation statements)

References 61 publications

(113 reference statements)

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“…Electronic structure calculations confirm the formation of type I heterostructures but also highlight the direct role from the I-EA spacer in improving the vertical transport. DFT-calculated effective masses for holes reach values down to 1.8 m e , comparable to promising organic molecular semiconductors, like rubrene or BTBT. − …”

Section: Introductionmentioning

confidence: 99%

Halide Containing Short Organic Monocations in n = 1–4 2D Multilayered Halide Perovskite Thin Films and Crystals

et al. 2023

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Low electronic band gap 2D multilayered (n = 3,4) leadiodide perovskites with formulas A′ 2 A n−1 Pb n I 3n+1 A″A n−1 Pb n I 3n+1 are of great interest for photovoltaics, with recent demonstrations of stable solar cell operation based on 2D/3D bilayered heterostructures. Still, the difficulty in achieving optimal phase control, with potential formation of mixed ndomains, is a limiting factor for the photovoltaic performance of 2D/3D heterostructures, and the current choice for multi n-layered compounds is limited. Here, we report synthesis and XRD characterization of novel (I-EA) 2 MA n−1 Pb n I 3n+1 (n = 1−4) compound series, along with the (Br-EA) 2 PbBr 4 (n = 1) compound, incorporating iodo-ethylammonium (I-EA) and bromo-ethylammonium (Br-EA) spacers. These halide-featuring spacers lead to a small lattice mismatch between the inorganic and organic components, which explains the successful formation of multi nlayered compounds. The presence of bromine or iodine in the interlayer space impacts on the dielectric and electronic properties of these materials. Periodic DFT simulations predict vertical hole effective mass for n = 1 (I-EA) 2 PbI 4 as small as 1.8 m e , comparable to popular organic semiconductors, like rubrene. UV−vis characterization sets the optical absorption onset of these materials around 1.71 eV for n = 3 and 4, hence suggesting that they can be successfully implemented in 2D/3D photovoltaic architectures.

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Section: Introductionmentioning

confidence: 99%

Halide Containing Short Organic Monocations in n = 1–4 2D Multilayered Halide Perovskite Thin Films and Crystals

et al. 2023

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“…3,4 This interest arises from the many applications of semiconductors in devices capable of converting an electrical power into light, OLEDs, with a broad spectrum of tunability enabled by the donor or acceptor chemistry, and also electrical devices based on semiconductors such as field effect transistors. 5,6 In addition, the optical properties of such co-crystal semiconductors, combined with their needle like crystal habit, allow for potential applications in photonics as waveguides, where light from an external light source with an energy below the gap or the luminescence of the co-crystal can be guided. 7 Crucial to the many possible applications of these materials as semiconductors are the energy values of the frontier orbitals, i.e.…”

Section: Introductionmentioning

confidence: 99%

Charge transfer modulation in charge transfer co-crystals driven by crystal structure morphology

Fontanesi

Solano

Inaudi

et al. 2022

Phys. Chem. Chem. Phys.

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“…In general, the HOMO level of a complex is deeper than that of the component donor due to the charge-transfer interaction, and this is the reason that not all hole-transporting materials show hole transport in the charge-transfer complexes. Alkoxy-BTBT with a comparatively shallow HOMO level has been reported, 51 but the complexes still exhibit electron-only transport due to the HOMO/LUMO orthogonality. Both the energy level and the nonorthogonality requirements are to be fulfilled to realize ambipolar transport.…”

Section: ■ Discussionmentioning

confidence: 99%

“…Benzothienobenzothiophene (BTBT) complexes have deep HOMO levels (Figure a) ,− and do not show hole transport. In general, the HOMO level of a complex is deeper than that of the component donor due to the charge-transfer interaction, and this is the reason that not all hole-transporting materials show hole transport in the charge-transfer complexes.…”

Section: Discussionmentioning

confidence: 99%

Transistor Properties of Charge-Transfer Complexes─Combined Requirements from Energy Levels and Orbital Symmetry

et al. 2023

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Tetracyanoquinodimethane (TCNQ) complexes of fluorene, dibenzofuran, dibenzothiophene, terphenyl, dithienothiophene, and carbazole show n-channel transistor properties, whereas that of diaminoterphenyl and phenothiazine exhibits ambipolar characteristics. Ambipolar transport is observed when the highest occupied molecular orbital (HOMO) level of the donor–acceptor complex is located above the ordinary hole transport limit. Since the HOMO of the charge-transfer complex is deeper than that of the component donor owing to the charge-transfer interaction, not all hole-transporting materials show hole transport in the charge-transfer complexes. In addition, the effective (super-exchange) transfer integrals have to be sufficiently large; this is frequently not satisfied when the donor HOMO is practically orthogonal to the acceptor’s lowest unoccupied molecular orbital (LUMO). By applying these criteria to calculations starting from the crystal structures, transistor properties of mixed stack charge-transfer complexes are explained.

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Charge transfer complexes of a benzothienobenzothiophene derivative and their implementation as active layer in solution-processed thin film organic field-effect transistors

Abstract: Herein, we report on the synthesis and structural characterization of novel charge transfer (CT) complexes of the benzothienobenzothiophene derivative C8O-BTBT-OC8 with the series of FxTCNQ derivatives (x= 2,4). The degree...

Cited by 12 publications

References 61 publications

Halide Containing Short Organic Monocations in n = 1–4 2D Multilayered Halide Perovskite Thin Films and Crystals

Halide Containing Short Organic Monocations in n = 1–4 2D Multilayered Halide Perovskite Thin Films and Crystals

Charge transfer modulation in charge transfer co-crystals driven by crystal structure morphology

Transistor Properties of Charge-Transfer Complexes─Combined Requirements from Energy Levels and Orbital Symmetry

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