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Highly Contorted 1,2,5‐Thiadiazole‐Fused Aromatics for Solution‐Processed Field‐Effect Transistors: Synthesis and Properties
Author(s) -
Shi Xin,
Liu Shuli,
Liu Chunming,
Hu Yueming,
Shi Saihua,
Fu Nina,
Zhao Baomin,
Wang Zhaohui,
Huang Wei
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600675
Subject(s) - organic field effect transistor , homo/lumo , molecule , materials science , absorption spectroscopy , analytical chemistry (journal) , field effect transistor , differential scanning calorimetry , spectroscopy , chemistry , crystallography , transistor , organic chemistry , optics , voltage , physics , quantum mechanics , thermodynamics
A straightforward strategy has been used to construct 1,2,5‐thiadiazole‐fused 12‐ring π systems through twofold Stille coupling and subsequent cyclodehydrogenation by utilizing the building blocks of naphthodithiophene and 5,6‐substituted benzo[ b ]‐2,1,3‐thiadidazole. Molecules 1 a and 1 b , which exhibit highly contorted π surfaces, show a butterfly‐shaped conformation according to DFT calculations. Within the molecules, a plane‐to‐plane angle of 44.8° was found. UV/Vis absorption, thermogravimetric analysis, differential scanning calorimetry, and cyclic voltammetry (CV) were used to study their physical properties. Strong intermolecular interactions of the nonplanar molecules were also observed by concentration‐dependent 1 H NMR spectroscopy measurements and thin‐film XRD characterization. The low‐lying LUMO and high‐lying HOMO levels of the molecules are −3.73 and −5.48 eV, respectively, as estimated from CV measurements; this indicates their potential as semiconducting materials for solution‐processed organic field‐effect transistors (OFETS). A field‐effect hole mobility of up to 0.035 cm 2 V −1 s −1 , a threshold voltage of 6.98 V, and a current on/off ratio of 8.65×10 5 in air for 1 a have been demonstrated with the top‐contact bottom‐gate field‐effect transistor device structures; this represents an important step toward the solution‐processed OFET application of contorted aromatics.