4.8 Article

Emerging Disordered Layered-Herringbone Phase in Organic Semiconductors Unveiled by Electron Crystallography

期刊

CHEMISTRY OF MATERIALS
卷 34, 期 1, 页码 72-83

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.chemmater.1c02793

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资金

  1. JST CREST from the Japan Science and Technology Agency (JST) [JPMJCR18J2]
  2. JSPS KAKENHI from the Japan Society for the Promotion of Science (JSPS) [JP19H05321, JP19H02579, JP21H04651, JP21K05209]
  3. JST-Mirai Program [JPMJMI20G5]
  4. Cyclic Innovation for Clinical Empowerment (CiCLE) from the Japan Agency for Medical Research and Development, AMED

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The study develops solution-processable organic semiconductors based on unsymmetric substitution of BTBT, showcasing formation of distinctive solid crystalline phases when substituents are similar, and bilayer-type crystalline phase when substituents are unsymmetrical. Controllable various phases are demonstrated in layered organic semiconductors through correlation and competition among different packing structures.
The control of two-dimensional layered crystalline and/or liquid crystalline phases for pi-extended organic molecules is crucial for expanding the potential of organic electronic materials and devices. In this work, we develop unique solution-processable organic semiconductors based on the unsymmetric substitution of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) with two different substituents, namely, phenylethynyl (PE) and normal alkyl with different chain lengths n (-CnH2n+1), both of which exhibit structural flexibility while maintaining the rod-like nature over the entire molecule. A distinctive layered solid crystalline phase, analogous to the smectic liquid crystalline phase, is obtainable in PE-BTBT-C-n at n = 6, where the substituent lengths are almost the same. The BTBT moiety maintains a rigid layered-herringbone (LHB) packing, whereas the molecular long axis exhibits a complete orientational disorder. We refer to this packing as disordered LHB (d-LHB), the unique geometry of which can be analyzed by the emerging technique of microcrystal electron diffraction crystallography. The intermolecular core-core interactions stabilize the d-LHB packing, enabling a relatively high field-effect mobility of approximately 3 cm(2) V-1 s(-1). In contrast, PE-BTBT-Cn with longer alkyl chains (n = 8, 10, 12) exhibits higher mobility of approximately 7 cm(2) V-1 s(-1) by constituting bilayer-type LHB (b-LHB), which is associated with the unsymmetrical length of the substituents. We discuss the correlation and competition among the d-LHB, b-LHB, and smectic liquid crystalline phases based on the structural, thermal, and transistor characteristics. These findings demonstrate the controllability of various phases in layered organic semiconductors.

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