Halogen Bonding as a Tool to Control Morphology and Charge Transport in Organic Semiconductors

Abstract The solid‐state structure and morphology of organic semiconductors (OSCs) are critical in determining the performance of organic electronic devices, as they directly influence charge carrier mobility. Improved molecular packing and ordering are key to achieving better device performance. While halogen bonding (XB) has been extensively used in supramolecular crystal engineering, its potential for organic electronics remains largely untapped. Here, we show that strong and directional XB can significantly enhance the morphology and optoelectronic properties of a pyridine‐substituted naphthalene diimide (NDI) derivative. By employing various XB donors with differing interaction strengths and comparing them to a nonbonding reference compound, we achieve a two‐orders‐of‐magnitude improvement in field‐effect mobility and I ON ‐ I OFF ratio. Furthermore, the geometric substitution pattern of the XB donors is found to strongly influence molecular packing, crystalline domain formation, and, ultimately, device performance.

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Publication Details

Journal
Angewandte Chemie
Published
2025-03-13
DOI
https://doi.org/10.1002/ange.202424979
Primary Topic
Semiconductor materials and devices
Type
article
Field-Weighted Citation Impact
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article

Halogen Bonding as a Tool to Control Morphology and Charge Transport in Organic Semiconductors

Tero‐Petri Ruoko, Arri Priimägi, Silan Zhang, Marc‐Antoine Stoeckel et al.
Angewandte Chemie
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article

Halogen Bonding as a Tool to Control Morphology and Charge Transport in Organic Semiconductors

Tero‐Petri Ruoko, Arri Priimägi, Silan Zhang, Marc‐Antoine Stoeckel, Rakesh Puttreddy, Paolo Samorı́, Nuno R. Candeias, Han Young Woo, Ziang Wu, Simone Fabiano, Chi‐Yuan Yang
article en

Abstract

Abstract The solid‐state structure and morphology of organic semiconductors (OSCs) are critical in determining the performance of organic electronic devices, as they directly influence charge carrier mobility. Improved molecular packing and ordering are key to achieving better device performance. While halogen bonding (XB) has been extensively used in supramolecular crystal engineering, its potential for organic electronics remains largely untapped. Here, we show that strong and directional XB can significantly enhance the morphology and optoelectronic properties of a pyridine‐substituted naphthalene diimide (NDI) derivative. By employing various XB donors with differing interaction strengths and comparing them to a nonbonding reference compound, we achieve a two‐orders‐of‐magnitude improvement in field‐effect mobility and I ON ‐ I OFF ratio. Furthermore, the geometric substitution pattern of the XB donors is found to strongly influence molecular packing, crystalline domain formation, and, ultimately, device performance.

Angewandte ChemieVol. 137(21)
Linköping University (SE), Centre National de la Recherche Scientifique (FR), Tampere University (FI), Korea University (KR), Department of Science,Technology and Innovation (ZA), Institut de Science et d'Ingénierie Supramoléculaires (FR), Wallenberg Wood Science Center (SE), Department of Science and Technology and Biotechnology (IN), Rede de Química e Tecnologia (PT), University of Aveiro (PT), Université de Strasbourg (FR), University of Jyväskylä (FI)
Openalex Percentile: Top 96%
Semiconductor materials and devices
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