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Structure–Property Correlation behind the High Mobility of Carbazolocarbazole

  • Miriam Más-Montoya
    Miriam Más-Montoya
    Department of Organic Chemistry, Faculty of Chemistry, University of Murcia, Campus of Espinardo, 30100 Murcia, Spain
  • Stamatis Georgakopoulos
    Stamatis Georgakopoulos
    Department of Organic Chemistry, Faculty of Chemistry, University of Murcia, Campus of Espinardo, 30100 Murcia, Spain
  • José Pedro Cerón-Carrasco
    José Pedro Cerón-Carrasco
    Bioinformatics and High Performance Computing Group, Universidad Católica San Antonio de Murcia (UCAM), Avda. Jerónimos, 135, 30107 Guadalupe, Murcia, Spain
  • José Pérez
    José Pérez
    Departamento de Ingeniería Minera, Geológica y Cartográfica, Área de Química Inorgánica, Regional Campus of International Excellence “Campus Mare Nostrum”, Universidad Politécnica de Cartagena, 30203 Cartagena, Spain
    More by José Pérez
  • Alberto Tárraga
    Alberto Tárraga
    Department of Organic Chemistry, Faculty of Chemistry, University of Murcia, Campus of Espinardo, 30100 Murcia, Spain
  • , and 
  • David Curiel*
    David Curiel
    Department of Organic Chemistry, Faculty of Chemistry, University of Murcia, Campus of Espinardo, 30100 Murcia, Spain
    *E-mail: [email protected]
    More by David Curiel
Cite this: J. Phys. Chem. C 2018, 122, 22, 11736–11746
Publication Date (Web):May 16, 2018
https://doi.org/10.1021/acs.jpcc.8b03878
Copyright © 2018 American Chemical Society

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    Supporting Info (2)»

    Abstract

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    A comparative study of carbazolocarbazole isomers and their respective N-alkyl derivatives confirms the good performance of carbazolo[2,1-a]carbazole as hole-transporting material in organic field effect transistors. The azaphenacene structure of this molecule forms a dense packing promoted by particularly short longitudinal shifts between molecules establishing face-to-face and edge-to-face interactions. Computational calculations have determined an almost isotropic 2D transport environment within a lamellar structure. This favorable solid state arrangement, in combination with appropriate interfacial layers, has led to a high mobility (1.3 cm2 V–1 s–1) that validates the aptitude of this molecular material as an organic semiconductor.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jpcc.8b03878.

    • NMR spectra, thermal characterization, cyclic voltammetry, polystyrene AFM, and stability of transfer characteristics (PDF)

    • CIf file for molecule 3 (CIF)

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    Cited By

    This article is cited by 6 publications.

    1. Paula Gómez, Stamatis Georgakopoulos, Miriam Más-Montoya, Jesús Cerdá, José Pérez, Enrique Ortí, Juan Aragó, David Curiel. Improving the Robustness of Organic Semiconductors through Hydrogen Bonding. ACS Applied Materials & Interfaces 2021, 13 (7) , 8620-8630. https://doi.org/10.1021/acsami.0c18928
    2. Miriam Más-Montoya, María F. Montenegro, Arturo Espinosa Ferao, Alberto Tárraga, José Neptuno Rodríguez-López, David Curiel. Rigid π-Extended Boron Difluoride Complex with Mega-Stokes Shift for Bioimaging. Organic Letters 2020, 22 (9) , 3356-3360. https://doi.org/10.1021/acs.orglett.0c00782
    3. Paula Gómez, Jesús Cerdá, Miriam Más-Montoya, Stamatis Georgakopoulos, Iván da Silva, Antonio García, Enrique Ortí, Juan Aragó, David Curiel. Effect of molecular geometry and extended conjugation on the performance of hydrogen-bonded semiconductors in organic thin-film field-effect transistors. Journal of Materials Chemistry C 2021, 9 (33) , 10819-10829. https://doi.org/10.1039/D1TC01328A
    4. Christoph M. Hendrich, Valentin D. Hannibal, Lukas Eberle, Leif E. Hertwig, Ute Zschieschang, Frank Rominger, Matthias Rudolph, Hagen Klauk, A. Stephen K. Hashmi. Gold‐Catalyzed Synthesis of π‐Extended Carbazole‐Based Systems and their Application as Organic Semiconductors. Advanced Synthesis & Catalysis 2021, 363 (5) , 1401-1407. https://doi.org/10.1002/adsc.202001461
    5. Tian Liu, Kuangshi Sun, Wei Shen, Rongxing He, Ming Li. Meta‐Stable Molecular Configuration Enables Thermally Stable and Solution Processable Organic Charge Transporting Materials. Advanced Functional Materials 2020, 30 (24) https://doi.org/10.1002/adfm.202000729
    6. Stamatis Georgakopoulos, Miriam Más-Montoya, José Pérez, Germán Ortuño, Alberto Tárraga, David Curiel. Interfacial and bulk charge transport in indolo[2,3-a]carbazole. Synthetic Metals 2020, 261 , 116308. https://doi.org/10.1016/j.synthmet.2020.116308