Face-on oriented thermolabile Boc-isoindigo/thiophenes small molecules: From synthesis to OFET performance. (January 2020)

• Record Type: Journal Article
• Authors: Shaker, Mohamed; Park, Byoungwook; Lee, Seongyu; Lee, Kwanghee
• Is Part Of: Dyes and pigments. Volume 172(2020)
• Publication Date: 2020-01
• Subjects: Tert-butoxycarbonyl-isoindigo -- Thermal decarboxylation -- Hydrogen bonding -- Ambipolar behavior -- Photovoltaic performances -- Synthesis; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2019.107784
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A new series of protected isoindigo (ID) based solution processable donor-acceptor type of small molecules was synthesized. Tert-butoxycarbonyl (t-Boc) substituted isoindigo is used as the acceptor unit and oligothiophene derivatives as the donor units. Thermal decarboxylation of small molecules films at 200 °C eliminated the t-Boc side groups. The cleavage of the protecting group formed a variety of N–H …. .O=C hydrogen bonding across the lactam structures of the isoindigo. The molecular orientation during the thermal decarboxylation of ID-Boc to ID-H was examined using X-ray diffraction and atomic force microscopy. The H-bonding formation and its impact on the optical, thermal, electrochemical and ambipolar behavior were investigated. Graphical abstract: Image 1 Highlights: H-bonding self-organized isoindigo based small molecules were synthesized and characterized. During thermal deprotection, the targeted materials showed face on orientation in the solid state. The hole mobility is dramatically a thousandfold increased after thermal deprotection.