Article, 2023

Supramolecular Self-Assembly of Diketopyrrolopyrrole with Unprecedented Photoconductivity

ACS Applied Electronic Materials, ISSN 2637-6113, Volume 5, 9, Pages 5093-5102, 10.1021/acsaelm.3c00845

Contributors

Maity, Nilabja 0000-0001-6341-9704 [1] Sharma, Manoj Kumar 0009-0004-5740-0985 [1] Ghosh, Samrat 0000-0002-5946-3013 [2] [3] Huss-Hansen, Mathias K 0000-0003-4487-508X [4] Roy, Ahin 0000-0002-9515-2562 [1] Narayanan, Ravishankar 0000-0003-0012-046X [1] Knaapila, Matti Pekka 0000-0002-4114-9798 [5] Matsuda, Wakana [3] Seki, Shuhei 0000-0001-7851-4405 (Corresponding author) [3] Patil, Satish 0000-0003-3884-114X (Corresponding author) [1]

Affiliations

  1. [1] Indian Institute of Science Bangalore
    2. [NORA names: India; Asia, South];
  2. [2] Central Leather Research Institute
    3. [NORA names: India; Asia, South];
  3. [3] Kyoto University
    4. [NORA names: Japan; Asia, East; OECD];
  4. [4] University of Southern Denmark
    5. [NORA names: SDU University of Southern Denmark; University; Denmark; Europe, EU; Nordic; OECD];
  5. [5] Norwegian University of Science and Technology
    6. [NORA names: Norway; Europe, Non-EU; Nordic; OECD]

Abstract

The oscillation of chemical bonds in molecular semiconductors plays a key role in fragmenting the electric conducting pathways due to the large fraction of free volumes, acting as “trap sites” for charge carriers. Incorporating directional noncovalent chemical bonds between the monomeric unit in organic semiconductors is an excellent approach to reducing thermally induced structural fluctuations, resulting in a decrease in a trap densities. In this work, we utilize noncovalent interactions in diketopyrrolopyrrole (DPP)-based supramolecular assembled systems to enhance or tune the photoconductivity and charge transport properties. Infinitesimal molecular design by substituting different side chains and introducing intramolecular dihedral angles leads to a notable difference in solid-state packing, transient photoconductivity, and thin film morphology. Grazing incidence wide-angle X-ray scattering, and thin film X-ray diffraction measurements reveal that the packing order is enhanced for hexyl substituted DPP derivatives, resulting in high intrinsic charge carrier mobility of ∑μ = 1.7 cm2 V–1 s–1. At the microscopic level, electron microscopy reveals that the unique self-assembly remarkably improves the structural order via directional hydrogen bonding. These findings exemplify that the supramolecular self-assembly strategy via hydrogen bonding networks is an efficacious way to reduce the molecular vibration and structural defects in molecular semiconductors and ameliorate the performance in optoelectronic devices.

Keywords

Supramolecular, X-ray diffraction measurements, X-ray scattering, angle, approach, bond network, bonds, carriers, chain, charge, charge carriers, charge transport properties, chemical bonding, conduction pathways, decrease, defects, density, design, devices, diffraction measurements, dihedral angle, diketopyrrolopyrrole, directional hydrogen bonds, efficacious way, electrically conductive pathways, electron, electron microscopy, excellent approach, film morphology, findings, fluctuations, fraction, fraction of free volume, free volume, grazing, grazing incidence wide-angle X-ray scattering, hexyl, hydrogen, hydrogen bond network, hydrogen bonds, interaction, intramolecular dihedral angle, levels, measurements, microscopic level, microscopy, mobility, molecular design, molecular semiconductors, molecular vibrations, monomeric units, morphology, network, noncovalent interactions, optoelectronic devices, order, organic semiconductors, oscillations, packing, packing order, pathway, performance, photoconductivity, properties, scattering, self-assembly, self-assembly strategy, semiconductor, side, side chains, sites, solid-state packing, strategies, structural defects, structural fluctuations, structural order, supramolecular assembly system, supramolecular self-assembly, supramolecular self-assembly strategy, system, thin film morphology, thin-film X-ray diffraction measurement, transient photoconductivity, transport properties, trap density, trapping sites, traps, unique self-assembly, units, vibration, volume, way, wide-angle X-ray scattering

Funders

  • Japan Society for the Promotion of Science
  • Department of Science and Technology
  • Engineering and Physical Sciences Research Council
  • Science and Engineering Research Board
  • Department for Business, Energy and Industrial Strategy
  • Indian Institute of Science Bangalore
  • Council of Scientific and Industrial Research

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