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π‐Extended Pyrrole‐Fused Heteropine: Synthesis, Properties, and Application in Organic Field‐Effect Transistors

Weifan Wang, Fiona Hanindita, Yusei Tanaka, Kotaro Ochiai, Hiroyasu Sato, Yongxin Li, Takuma Yasuda, Shingo Ito

2022Angewandte Chemie International Edition30 citationsDOI

Abstract

Abstract Sulfur‐embedded polycyclic aromatic compounds have been used as building blocks for numerous organic semiconductors over the past few decades. While the success is based on thiophene‐containing compounds, aromatic compounds that contain thiepine, a sulfur‐containing seven‐membered‐ring arene, has been less well investigated. Here we report the synthesis and properties of π‐extended pyrrole‐fused heteropine compounds such as thiepine and oxepine. A π‐extended pyrrole‐fused thiepine exhibited a “pitched π‐stacking” structure in the crystal, and exhibited a high charge carrier mobility of up to 1.0 cm 2 V −1 s −1 in single‐crystal field‐effect transistors.

Topics & Concepts

ThiophenePyrroleStackingSulfurRing (chemistry)Organic semiconductorAromaticityChemistrySingle crystalCrystal (programming language)Materials scienceTransistorOrganic chemistryCrystallographyMoleculeComputer scienceVoltageProgramming languagePhysicsQuantum mechanicsOrganic Electronics and PhotovoltaicsPerovskite Materials and ApplicationsAdvanced Memory and Neural Computing
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