Alberto Riaño

University of the Basque Country

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Manuel Melle‐Franco

University of Aveiro

Aurelio Mateo‐Alonso

Polymat

Juan T. López Navarrete

University of Asia and the Pacific

José L. Segura

Universidad Complutense de Madrid

Akinori Saeki

Osaka University

Rocío Ponce Ortiz

Universidad de Málaga

Juan Casado

Universidad de Málaga

Antonio Facchetti

Northwestern University

Tobin J. Marks

Northwestern University

Iratxe Arrechea‐Marcos

Universidad de Málaga

Cooperative Institutions

Universidad Complutense de Madrid

Northwestern University

Universidad de Málaga

Centro Médico Sanitas Málaga

University of the Basque Country

Rede de Química e Tecnologia

Centre National de la Recherche Scientifique

University of Bologna

Center for Light Energy Activated Redox Processes

Universidad Autónoma de Madrid

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Giant Star‐Shaped Nitrogen‐Doped Nanographenes

Angewandte Chemie (2018)

Juan P. Mora‐Fuentes Alberto Riaño Diego Cortizo‐Lacalle Akinori Saeki Manuel Melle‐Franco

Abstract Star‐shaped nanographenes (SNGs) are large monodisperse polycyclic aromatic hydrocarbons that are larger than a nanometer and have shown a lot of promise in a wide range of applications including electronics, energy conversion, and sensing. Herein, we report a new family of giant star‐shaped N‐doped nanographenes with diameters up to 6.5 nm. Furthermore, the high solubility of this SNG family in neutral organic solvents at room temperature allowed a complete structural, optoelectronic, and electrochemical characterisation, which together with charge transport studies illustrate their n‐type semiconducting character.

Nanometre

Star (game theory)

Dispersity

Organic Electronics

10.1002/ange.201811015

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Citations (16)

Synthesis of new derivatives of β‐carboline‐hydantoin

Journal of Heterocyclic Chemistry (1990)

Miguel F. Braña Mercedes Garrido María L. López-Rodrı́guez Pilar San Miguel M. J. MORCILLO

Abstract Reaction of tetrahydro‐β‐carboline‐3‐carboxylic acids 4a‐c with alkyl and phenyl isocyanates in acetone provide the corresponding 2,5‐disubstituted 1,3‐dioxo‐6 H ‐1,2,3,5,11,11a‐hexahydroimidazo[1,5‐ b ]‐β‐carbolines 2a‐r .

Hydantoin

10.1002/jhet.5570270342

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Citations (6)

Mechanically Interlocked Nitrogenated Nanographenes

Journal of the American Chemical Society (2020)

Alberto Riaño Marco Carini Manuel Melle‐Franco Aurelio Mateo‐Alonso

Herein, we report the synthesis of mechanically interlocked nitrogenated nanographenes. These systems have been obtained by clipping different tetralactam macrocycles around a 1.9 nm dumbbell-shaped nitrogenated nanographene. Thermal, optoelectronic, and electrochemical characterization of the different mechanically interlocked nanographenes evidence enhanced thermal and photochemical stability, and also absorption and emission properties that vary with the structure of the macrocycle.

Dumbbell

Thermal Stability

Characterization

10.1021/jacs.0c10345

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Even and odd oligothiophene-bridged bis-naphthalimides for n-type and ambipolar organic field effect transistors

Journal of Materials Chemistry C (2017)

Alberto Riaño Guzmán L. Espejo María José Mancheño Real Brian J. Eckstein Rafael C. González‐Cano

Which effect directs supramolecular packing? π–π stabilizing interactions between two NDI units or dipole–dipole couplings?

Ambipolar diffusion

Organic field-effect transistor

10.1039/c7tc02023f

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Citations (9)

Diseño, síntesis y estudio de sistemas moleculares electroactivos basados en tiofeno

Alberto Riaño

Organic molecular semiconductors are attractive for fabrication of costeffective, large-area, and mechanically flexible electronic devices. To date the applications of organic semiconductors include, but are not limited to, organic light-emitting diodes (OLEDs), organic thin-film transistors (OTFTs), organic solar cells (OSCs) and organic electrochromic devices (OECDs). During the past two decades, organic optoelectronic device performance has advanced dramatically. Such progress is the result of interdisciplinary research efforts from organic synthetic chemists to device engineers. In fact, the device performance is not only determined by the semiconductors but also closely related to materials combinations and integration, multilayer film morphologies and microstructures, as well as device structures. The main objective of this thesis, is the synthesis and modulation of the properties of different structures based on thiophene through their chemical modification to understand and explain their performance in (opto)electronic devices such as organic field effect transistors and organic solar cells. This thesis is divided into three chapters: - Chapter 1: Organic systems based on hexaazatriphenylene (HAT) and thiophene. - Chapter 2: Organic systems based on bis(naphthalene diimide) (NDI) and thiophene. - Chapter 3: Organic systems based on diketopyrrolopyrrole (DPP) and thiophene...

Organic semiconductor

Organic Electronics

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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)

CCDC 2033834: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Alberto Riaño Marco Carini Manuel Melle‐Franco Aurelio Mateo‐Alonso

10.5517/ccdc.csd.cc268ckf

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Citations (0)

Giant Star‐Shaped Nitrogen‐Doped Nanographenes

Angewandte Chemie International Edition (2018)

Juan P. Mora‐Fuentes Alberto Riaño Diego Cortizo‐Lacalle Akinori Saeki Manuel Melle‐Franco

Star-shaped nanographenes (SNGs) are large monodisperse polycyclic aromatic hydrocarbons that are larger than a nanometer and have shown a lot of promise in a wide range of applications including electronics, energy conversion, and sensing. Herein, we report a new family of giant star-shaped N-doped nanographenes with diameters up to 6.5 nm. Furthermore, the high solubility of this SNG family in neutral organic solvents at room temperature allowed a complete structural, optoelectronic, and electrochemical characterisation, which together with charge transport studies illustrate their n-type semiconducting character.

Nanometre

Organic Electronics

Dispersity

Star (game theory)

10.1002/anie.201811015

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Citations (39)

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)

Benzotrithiophenes vs. Benzo/Naptha-dithiophenes: The Effect of Star-Shaped versus Linear Conjugation on Their Electronic Structures

Iratxe Arrechea‐Marcos Rocio Ponce-Ortiz Alberto Riaño Paula Mayorga-Burruezo S. Loser

Star (game theory)

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