A NIR dye with high-performance n-type semiconducting properties. Issue 1 (23rd October 2015)

• Record Type: Journal Article
• Authors: Xie, Jiajun; Shi, Ke; Cai, Kang; Zhang, Di; Wang, Jie-Yu; Pei, Jian; Zhao, Dahui
• Is Part Of: Chemical science. Volume 7:Issue 1(2016:Jan.)
• Page Start: 499
• Page End: 504
• Publication Date: 2015-10-23
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5sc03045e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A novel hetero-polycyclic aromatic compound showing strong NIR absorption and high-performance n-type semiconducting properties is developed. A special metal-free C–C coupling serves as a pivotal step in constructing the polycyclic π-framework. Abstract : A novel hetero-polycyclic aromatic compound manifesting strong near-infrared (NIR) absorption as well as high-performance n-type semiconducting properties is developed. With an exceptionally low LUMO level at −4.7 eV, this NIR dye ( λ max ≈ 1100 nm, ε ≈ 10 5 mol −1 L cm −1 ) exhibits adequate stability under ambient conditions, with electron mobility up to 0.96 cm 2 V −1 s −1 measured in solution-processed organic field-effect transistors. A special metal-free C–C coupling serves as a pivotal step in constructing the polycyclic π-framework of this low-bandgap chromophore, by fusing an electron-deficient naphthalenediimide moiety with an electron-donating naphthalenediamine. Such a rare combination of extraordinary optical and semiconductive attributes is quite valuable for organic small molecules, and promising for unique applications in the opto-electronic field.