摘要/Abstract
将靛红和氮杂靛红衍生物单元分别与苊醌二甲酰亚胺进行Knoevenagel缩合，开发了两个结构新型、强缺电特性的异靛青衍生物受体单元，包括靛红并苊醌二甲酰亚胺单元（A1）和氮杂靛红并苊醌二甲酰亚胺单元（A2）.然后运用"双受体策略"，进一步设计并合成了两个含A1和A2受体单元的A-A型二联体共轭分子（BA1和BA2），并对比研究了吡啶氮原子对共轭分子的骨架结构、吸收光谱、能级结构以及载流子迁移率的影响.研究发现：相比经典的异靛蓝受体，A1和A2受体单元拥有更低的LUMO能级（ca.-4.0 eV）和更大的骨架共轭；相比A1和A2，二联体化合物BA1和BA2不仅拥有更大的骨架共轭和更好的分子对称性，而且在整个紫外-可见光区的展现出强的光捕获能力；吡啶氮原子的引入增强了A2和BA2的骨架共平面性以及电子亲和力，有效地降低了A2和BA2的HOMO和LUMO能级值.基于BA1和BA2薄膜，制备了n-型场效应晶体管器件，其电子迁移率分别达1.64×10-3和2.52×10-3 cm2·V-1·s-1.
关键词: 靛红, 苊醌二甲酰亚胺, 异靛青, 电子迁移率
Two highly electron-deficient, novel isoindigo (IID) derivative acceptor units, including isatin-fused acenaphthenequinone imide (A1) and nitrogen-doped isatin-fused acenaphthenequinone imide (A2), were designed and synthesized via Knoevenagel consendation reaction. In comparison with the well-known IID unit, both A1 and A2 acceptor units exhibit reduced LUMO energy levels (ca. -4.0 eV) and extended π-conjugation backbone owing to the incorporation of strongly electron-withdrawing acenaphthenequinone imide. The properties observed here for both A1 and A2 are thus indicative of promising potential in the development of n-type organic semiconductors. On the basis of both A1 and A2 acceptor units, two A-A type organic π-conjugated molecules (BA1 and BA2) were further designed and synthesized by self-coupling of two identical A1 or A2 acceptor units. The effect of pyridal nitrogen on the backbone structure, optical absorption, energy level, and carrier mobility of the as-prepared π-conjugated molecules is studied systematically. The comparative investigation reveals that self-coupling of dual acceptor units into BA1 and BA2 not only endows them with extended conjugation backbone and enhanced molecular symmetry, but also improves their light-capturing abilities in the whole ultraviolet-visible region as relative to their parent acceptor units (A1 and A2). Moreover, the pyridal N-containing BA1 and BA2 possess enhanced backbone coplanarity and electron affinity as compared to their parent units (A1 and A2), thereby leading to reduced HOMO and LUMO energy levels. Finally, n-type thin-film transistors are further fabricated by adopting both BA1 and BA2 as the active layers, affording the electron motilities of 1.64×10-3 and 2.52×10-3 cm2·V-1·s-1, respectively.
Key words: isatin, acenaphthenequinone imide, isoindigo, electron mobility
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