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Redox‐Stability of Alkoxy‐BDT Copolymers and their Use for Organic Bioelectronic Devices
Advanced Functional Materials ( IF 19.0 ) Pub Date : 2018-02-21 , DOI: 10.1002/adfm.201706325
Alexander Giovannitti 1 , Karl J. Thorley 1 , Christian B. Nielsen 2 , Jun Li 1 , Mary J. Donahue 3 , George G. Malliaras 4 , Jonathan Rivnay 5, 6 , Iain McCulloch 1, 7
Affiliation  

Organic semiconductors can be employed as the active layer in accumulation mode organic electrochemical transistors (OECTs), where redox stability in aqueous electrolytes is important for long‐term recordings of biological events. It is observed that alkoxy‐benzo[1,2‐b:4,5‐b′]dithiophene (BDT) copolymers can be extremely unstable when they are oxidized in aqueous solutions. The redox stability of these copolymers can be improved by molecular design of the copolymer where it is observed that the electron rich comonomer 3,3′‐dimethoxy‐2,2′‐bithiophene (MeOT2) lowers the oxidation potential and also stabilizes positive charges through delocalization and resonance effects. For copolymers where the comonomers do not have the same ability to stabilize positive charges, irreversible redox reactions are observed with the formation of quinone structures, being detrimental to performance of the materials in OECTs. Charge distribution along the copolymer from density functional theory calculations is seen to be an important factor in the stability of the charged copolymer. As a result of the stabilizing effect of the comonomer, a highly stable OECT performance is observed with transconductances in the mS range. The analysis of the decomposition pathway also raises questions about the general stability of the alkoxy‐BDT unit, which is heavily used in donor–acceptor copolymers in the field of photovoltaics.

中文翻译:

烷氧基-BDT共聚物的氧化还原稳定性及其在有机生物电子设备中的用途

有机半导体可以用作累积模式有机电化学晶体管(OECT)中的活性层,其中在水性电解质中的氧化还原稳定性对于长期记录生物事件很重要。观察到烷氧基苯并[1,2- b:4,5- b']二噻吩(BDT)共聚物在水溶液中氧化时可能非常不稳定。这些共聚物的氧化还原稳定性可以通过共聚物的分子设计来改善,其中观察到富电子共聚单体3,3'-二甲氧基-2,2'-联噻吩(MeOT2)降低了氧化电位,并通过离域和共振效应。对于共聚单体不具有稳定正电荷的相同能力的共聚物,观察到不可逆的氧化还原反应,形成醌结构,这不利于OECTs中材料的性能。由密度泛函理论计算得出的沿共聚物的电荷分布被认为是带电共聚物稳定性的重要因素。由于共聚单体的稳定作用,跨导在mS范围内,观察到了非常稳定的OECT性能。分解途径的分析也引发了有关烷氧基-BDT单元总体稳定性的问题,该单元在光伏领域中大量用于施主-受主共聚物中。
更新日期:2018-02-21
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