Thionating iso-diketopyrrolopyrrole-based polymers: from p-type to ambipolar field effect transistors with enhanced charge mobility†,Polymer Chemistry

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Thionating iso-diketopyrrolopyrrole-based polymers: from p-type to ambipolar field effect transistors with enhanced charge mobility†
Polymer Chemistry ( IF 4.1 ) Pub Date : 2018-03-05 00:00:00 , DOI: 10.1039/c8py00292d
Haichang Zhang _{1,

2,

3,

4,

5} , Kun Yang _{6,

7,

8,

9} , Kai Zhang _{1,

2,

3,

4,

5} , Zhenzhen Zhang _{1,

2,

3,

4,

5} , Qikun Sun _{1,

2,

3,

4,

5} , Wenjun Yang _{1,

2,

3,

4,

5}

Affiliation

In this paper, two donor–acceptor-type π-conjugated polymers (P1 and P2) with 4,4′-bis(2-ethylhexyl)-5,5′-bis(trimethyltin)dithieno[3,2-b:2′,3′-d]silole as the donor and iso-diketopyrrolopyrrole or iso-dithioketopyrrolopyrrole as the acceptor moiety were designed and synthesized via palladium-catalyzed Stille coupling, and their optical, electrochemical and organic field effect transistor (OFET) properties were investigated. P2 could be regarded as the simple thionated product of P1, however, only one atom difference has resulted in their significantly different optical and electronic properties. P2 exhibited an obviously bathochromic shift absorption compared to P1. Noticeably, P1 only showed a hole mobility of 0.09 cm² V⁻¹ s⁻¹, while P2 exhibited hole and electron mobilities of up to 0.49 cm² V⁻¹ s⁻¹ and 0.26 cm² V⁻¹ s⁻¹, respectively, which indicated that the thionation could not only improve charge mobility but also give the polymer ambipolar transporting properties. Quantum chemical calculations and electrochemical analysis revealed that the thionation could further optimize the frontier molecular orbitals and facilitate the charge injection. This work demonstrated that iso-dithioketopyrrolopyrroles could be promising building blocks for high-performance organic field effect transistors.

中文翻译：

异硫氰酸二酮基吡咯并吡咯基聚合物：具有增强的电荷迁移率的从p型到双极场效应晶体管†

在本文中，两个具有4,4'-双（2-乙基己基）-5,5'-双（三甲基锡）二硫代[3,2- b：2]的供体-受体型π共轭聚合物（P1和P2）'，3'- d ]噻咯作为供体和异二酮吡咯并吡咯或异二硫代作为受体部分设计并合成了通过钯催化的Stille偶联，和它们的光学，电化学和有机场效应晶体管（OFET）性能的影响。P2可以看作是P1的简单亚硫代产物，但是，只有一个原子的差异导致它们的光学和电子性质显着不同。P2与P1相比，表现出明显的红移吸收。值得注意的是，P1仅显示出0.09 cm ² V ^-1 s ^-1的空穴迁移率，而P2显示出高达0.49 cm ² V ^-1 s ^-1和0.26 cm ² V ^-1 s ^-1的空穴迁移率和电子迁移率。分别表明，硫磺化不仅可以改善电荷迁移率，而且还赋予聚合物双极性传输性质。量子化学计算和电化学分析表明，硫磺化可以进一步优化前沿分子轨道并促进电荷注入。这项工作表明，异二硫代酮基吡咯并吡咯可能是高性能有机场效应晶体管的有前途的构建基块。

更新日期：2018-03-05

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