Synthesis, characterization, and field-effect performance of the halogenated indolone derivatives. (January 2017)

• Record Type: Journal Article
• Authors: Wei, Congyuan; Zou, Jiabin; Zhu, Rui; Huang, Jianyao; Gao, Dong; Wang, Liping; Zhang, Weifeng; Liao, Yi; Yu, Gui
• Is Part Of: Dyes and pigments. Volume 136(2017)
• Page Start: 434
• Page End: 440
• Publication Date: 2017-01
• Subjects: Donor-acceptor compound -- Mobility -- Indole-2-one -- Organic field-effect transistors; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2016.09.005
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: In this paper we present the design and synthesis of three π-extended indolone derivatives, namely (3Z, 3′Z)-3, 3′-((5, 5′-((E)-ethene-1, 2-diyl)bis(thiophene-2, 5-diyl))bis(methanylylidene))bis(1-octylindolin-2-one) (3a ), (3Z, 3′Z)-3, 3′-((5, 5′-((E)-ethene-1, 2-diyl)bis(thiophene-2, 5-diyl))bis(methanylylidene))bis(5-fluoro-1-octylindolin-2-one) (3b ) and (3Z, 3′Z)-3, 3′-((5, 5′-((E)-ethene-1, 2-diyl)bis(thiophene-2, 5-diyl))bis(methanylylidene))bis(5-chloro-1-octylindolin-2-one (3c ), with ( E )-1, 2-di(thiophen-2-yl)ethene as the donor and indolin-2-ones as the acceptors. All of the three acceptor-donor-acceptor type molecules have high conjugations and planar energy-minimized conformations, which are beneficial to forming ordered molecular packing and facilitating charge transport in thin films. Additionally, to study the effect of halogenation, fluorine and chlorine atoms were introduced in terms of microscale and mesoscale molecular engineering.3b and3c show obviously different features of crystalline tendencies and morphologies compared with those of3a . Organic field-effect transistors based on the three small molecules display typical p-channel charge transport characteristics under ambient conditions. Fluorinated3b affords the highest mobility of 0.1 cm 2 V −1 s −1 among the three analogues, demonstrating that fluorination is a useful strategy to optimize the solid-state arrangement and device performances. Graphical abstract: Highlights: Acceptor-donor-acceptor type small molecules based on indolone were synthetized and characterized. The field-effect transistors were fabricated and the high mobility of 0.10 cm 2 V −1 s −1 was obtained. Halide effect was investigated by introducing fluorine and chlorine atoms in the five position of indolone.