Iratxe Arrechea‐Marcos

Universidad de Málaga

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Juan T. López Navarrete

University of Asia and the Pacific

Rocío Ponce Ortiz

Universidad de Málaga

M. Carmen Ruiz Delgado

Universidad de Málaga

José L. Segura

Universidad Complutense de Madrid

Xugang Guo

Southern University of Science and Technology

Alexandra Harbuzaru

Universidad de Málaga

María J. Mancheño

Universidad Complutense de Madrid

Han Guo

Huadong Hospital

Mar Ramos

Universidad Rey Juan Carlos

Rocio Ponce-Ortiz

Cooperative Institutions

Universidad Complutense de Madrid

Universidad de Málaga

Northwestern University

Instituto de Ciencia de Materiales de Madrid

University of Castilla-La Mancha

Centro Médico Sanitas Málaga

Southern University of Science and Technology

Consejo Superior de Investigaciones Científicas

Instituto de Ciencia de Materiales de Sevilla

University of Oregon

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D–A–D 2H-benzo[d][1,2,3]triazole derivatives as p-type semiconductors in organic field-effect transistors

RSC Advances (2018)

Iván Torres‐Moya Iratxe Arrechea‐Marcos Carlos Tardío José R. Carrillo Ángel Díaz‐Ortiz

A series of Donor-π-Acceptor-π-Donor compounds based on a 2H-benzo[d][1,2,3]triazole core branched with different alkynyl donor groups has been characterized and tested in organic field-effect transistors (OFETs). The electronic and molecular structures were elucidated through optical and vibrational spectroscopy in conjunction with DFT calculations. The results indicate that the planarity of the structure and the good intramolecular charge transfer from the electron-donating to the electron-withdrawing fragments play a critical role in the application of the compounds as semiconductors in OFET devices. The compounds were tested in a top-contact/bottom-gate thin film transistor architecture, and they behave as p-type semiconductors.

Organic field-effect transistor

Planarity testing

Organic semiconductor

10.1039/c8ra03246g

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Citations (15)

CCDC 1453353: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

Mithrabinda K. Poduval Iratxe Arrechea‐Marcos M. Carmen Ruiz Delgado Taiho Park Juan T. López Navarrete

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1ksbc1

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Citations (0)

Solution-processedN-trialkylated triindoles for organic field effect transistors

Journal of Materials Chemistry C (2017)

Constanza Ruiz Iratxe Arrechea‐Marcos Angela Benito-Hernández Enrique Gutiérrez‐Puebla Ángeles Monge

Self-assembly ofN-alkyl triindoles driven by CH–π interactions gives rise to highly aligned films successfully incorporated into solution-processed OFETs.

10.1039/c7tc03866f

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Citations (19)

(Semi)ladder-Type Bithiophene Imide-Based All-Acceptor Semiconductors: Synthesis, Structure–Property Correlations, and Unipolar n-Type Transistor Performance

Journal of the American Chemical Society (2018)

Yingfeng Wang Han Guo Alexandra Harbuzaru Mohammad Afsar Uddin Iratxe Arrechea‐Marcos

Development of high-performance unipolar n-type organic semiconductors still remains as a great challenge. In this work, all-acceptor bithiophene imide-based ladder-type small molecules BTIn and semiladder-type homopolymers PBTIn (n = 1–5) were synthesized, and their structure–property correlations were studied in depth. It was found that Pd-catalyzed Stille coupling is superior to Ni-mediated Yamamoto coupling to produce polymers with higher molecular weight and improved polymer quality, thus leading to greatly increased electron mobility (μe). Due to their all-acceptor backbone, these polymers all exhibit unipolar n-type transport in organic thin-film transistors, accompanied by low off-currents (10–10–10–9 A), large on/off current ratios (106), and small threshold voltages (∼15–25 V). The highest μe, up to 3.71 cm2 V–1 s–1, is attained from PBTI1 with the shortest monomer unit. As the monomer size is extended, the μe drops by 2 orders to 0.014 cm2 V–1 s–1 for PBTI5. This monotonic decrease of μe was also observed in their homologous BTIn small molecules. This trend of mobility decrease is in good agreement with the evolvement of disordered phases within the film, as revealed by Raman spectroscopy and X-ray diffraction measurements. The extension of the ladder-type building blocks appears to have a large impact on the motion freedom of the building blocks and the polymer chains during film formation, thus negatively affecting film morphology and charge carrier mobility. The result indicates that synthesizing building blocks with more extended ladder-type backbone does not necessarily lead to improved mobilities. This study marks a significant advance in the performance of all-acceptor-type polymers as unipolar electron transporting materials and provides useful guidelines for further development of (semi)ladder-type molecular and polymeric semiconductors for applications in organic electronics.

Acceptor

Electron Mobility

10.1021/jacs.8b02144

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Citations (196)

CCDC 1021612: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Cristina Mayor Ruíz Iratxe Arrechea‐Marcos Angela Benito-Hernández Enrique Gutiérrez‐Puebla Ángeles Monge

10.5517/ccdc.csd.cc13927q

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Tuning of the Electronic Levels of Oligothiophene–Naphthalimide Assemblies by Chemical Modification

Chemistry - A European Journal (2016)

Alejandro de la Peña Iratxe Arrechea‐Marcos María J. Mancheño M. Carmen Ruiz Delgado Juan T. López Navarrete

Inversion of the connections of amidine linkers combined with controlled oligothiophene chain catenation in oligothiophene-naphthalimide assemblies provides an efficient method to tune the HOMO and LUMO values in this type of assemblies. This modification also suppresses the intramolecular charge transfer (ICT) band normally found in this type of derivatives, also delocalizing the frontier molecular orbitals over the whole conjugated skeleton. The resultant assemblies were used in the fabrication of field-effect transistors, which showed well-balanced ambipolar transport.

Ambipolar diffusion

Catenation

HOMO/LUMO

10.1002/chem.201602082

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Citations (12)

Benzotrithiophene versus Benzo/Naphthodithiophene Building Blocks: The Effect of Star‐Shaped versus Linear Conjugation on Their Electronic Structures

Chemistry - A European Journal (2016)

Alberto Riaño Iratxe Arrechea‐Marcos María J. Mancheño Paula Mayorga Burrezo Alejandro de la Peña

Abstract The synthesis, characterization, and optical properties of a novel star‐shaped oligothiophene with a central rigid trithienobenzene (BTT) core and diketopyrrolopyrrole (DPP) units are reported and compared with homologous linear systems based on the benzodithiophene (BDT) and the naphthodithiophene (NDT) units end capped with DPPs. This comparison is aimed at elucidating the effect of the star‐shaped configuration versus linear conformation on the optical and electrical properties. Electronic and vibrational spectroscopies, together with transient absorption spectroscopy, scanning electronic microscopy, and DFT calculations are used to understand not only the molecular properties of these semiconductors, but also to analyze the supramolecular aggregation in these derivatives. We conclude that although the subject star‐shaped derivative is not optimal in terms of π‐conjugation, its extended BTT unit significantly favors intermolecular π‐stacking interactions, which is interesting for their applications in devices. Field‐effect transistors and solar cells were fabricated with these new molecular semiconductors and the performance difference discussed.

Star (game theory)

10.1002/chem.201504526

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Citations (14)

Understanding organic materials performance in field-effect transistors

Rocio Ponce-Ortiz Iratxe Arrechea‐Marcos Guzmán L. Espejo Juan T. López Navarrete José L. Segura

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Molecular aggregation of naphthalimide organic semiconductors assisted by amphiphilic and lipophilic interactions: a joint theoretical and experimental study

Physical Chemistry Chemical Physics (2017)

Iratxe Arrechea‐Marcos Paula de Echegaray María J. Mancheño M. Carmen Ruiz Delgado Mar Ramos

Amphiphilic and lipophilic donor-acceptor naphthalimide-oligothiophene assemblies exhibiting almost identical intramolecular properties, but differing in their intermolecular interactions, have been synthesized. Here we analyze the effect of replacing the normally used lipophilic alkyl chains with hydrophilic ones in directing molecular aggregation from an antiparallel to a parallel stacking. This different molecular packing of the amphiphilic, NIP-3TAmphi, and lipophilic, NIP-3TLipo, systems is assessed by electronic spectroscopies, scanning electronic microscopy and DFT quantum-chemical calculations. Theoretical calculations indicate that the presence of amphiphilic interactions promotes a face-to-face parallel arrangement of neighbor molecules, which induces improved electronic coupling and therefore enhances the charge transport ability and photoconducting properties of this type of materials. Time of flight and photoconducting measurements are used to determine the impact of the amphiphilic and lipophilic interactions on their possible performance in optoelectronic devices.

Antiparallel (mathematics)

Amphiphilic molecule

Acceptor

10.1039/c6cp06819g

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Citations (9)

Extending Hexaazatriphenylene with Mono-/Bithiophenes in Acceptor–Donor Diads and Acceptor–Donor–Acceptor Triads

The Journal of Physical Chemistry C (2016)

María Moreno Oliva Alberto Riaño Iratxe Arrechea‐Marcos Mar Ramos Rafael Gómez

Three new hexaazatriphenylene (HAT)-based electron-accepting molecules with octupolar disc-like symmetry that combine the HAT core with six branches of electron-donor thiophenes in two modalities have been synthesized: (i) with six donor thiophenes and bithiophenes delineating a six-donor-to-one-acceptor (6–1) profile and (ii) with six donor–acceptor branches configuring a 6–6–1 acceptor–donor–acceptor triad. The 6-fold accumulation of donors and acceptors in the periphery of the HAT core is expected to tune the molecular electronic and optical properties. An exhaustive analysis of these properties as a function of the 6–1 and 6–6–1 stoichiometry of the molecules is described by combining a palette of experimental spectroscopic techniques such as electronic absorption (from the ground electronic and excited states), emission (fluorescence and phosphorescence), ultraviolet photoelectron spectroscopy, spectroelectrochemistry, and vibrational Raman have been implemented, all combined with electrochemistry and molecular theoretical modeling. A particular focus on the charged species and the charge distribution around the 6–1 and 6–6–1 patterns is conducted. Structure–property relationships have been outlined. The complete understanding of all these properties might help to design improved chromophores based on the HAT structure and to anticipate new properties.

Acceptor

Electron acceptor

Chromophore

Electron donor

10.1021/acs.jpcc.6b08123

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Citations (5)