Highly Contorted 1, 2, 5‐Thiadiazole‐Fused Aromatics for Solution‐Processed Field‐Effect Transistors: Synthesis and Properties. Issue 15 (15th July 2016)

• Record Type: Journal Article
• Authors: Shi, Xin; Liu, Shuli; Liu, Chunming; Hu, Yueming; Shi, Saihua; Fu, Nina; Zhao, Baomin; Wang, Zhaohui; Huang, Wei
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 15(2016)
• Page Start: 2188
• Page End: 2200
• Publication Date: 2016-07-15
• Subjects: aromaticity -- conjugation -- fused-ring systems -- polycyclic aromatic hydrocarbons -- synthesis design; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201600675
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: 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. Molecules1 a and1 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 for1 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. Abstract : Fused FET : 1, 2, 5‐Thiadiazole‐fused 12‐ring π systems exhibiting highly contorted π surfaces with a plane‐to‐plane angle of 44.8° have been developed (see figure). 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 for1 a have been demonstrated with top‐contact bottom‐gate field‐effect transistor (FET) device structures. This represents an important step toward the solution‐processed organic FET application of contorted aromatics.