Two semiconducting naphthalene bisimides were comparatively studied: NBI–(TAA)₂, symmetrically N-substituted with triaryl amine and asymmetric NBI–TAA–Oc with triaryl amine and octyl N-substituents. Both compounds show very similar spectroscopic and redox properties but differ in their supramolecular organization. As evidenced by STM, in monolayers on HOPG they form ordered 2D structures, however of different packing patterns. NBI–(TAA)₂ does not form ordered 3D structures, yielding amorphous thin films whereas films of NBI–TAA–Oc are highly crystalline. DFT calculations predict the ionization potential (IP) of 5.22 eV and 5.18 eV for NBI–TAA–Oc and NBI–(TAA)₂, respectively, as well as the electron affinity values (EA) of −3.25 eV and −3.22 eV. These results are consistent with the cyclic voltammetry data which yield similar values of IP (5.20 eV and 5.19 eV) and somehow different values of EA (−3.80 eV and −3.83 eV). As judged from these data, both semiconductors should exhibit ambipolar behavior. Indeed, NBI–TAA–Oc is ambipolar, showing hole and electron mobilities of 4.5 × 10⁻⁵ cm²/(V s) and of 2.6 × 10⁻⁴ cm²/(V s), respectively, in the field effect transistor configuration. NBI–(TAA)₂ is not ambipolar and yields field effect only in the p-channel configuration. This different behavior is rationalized on the basis of structural factors.

中文翻译：

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用三芳基胺 非对称和对称地N取代的萘二甲酰亚胺–光谱，电化学，电子和自组装性能的比较†

两种半导体 萘对双酰亚胺进行了比较研究：NBI–（TAA）₂，被三芳基胺对称地N-取代，而不对称的NBI–TAA–Oc被三芳基胺和辛基N-取代基取代。两种化合物均显示出非常相似的光谱和氧化还原特性，但它们的超分子组织不同。如STM所证明的，它们在HOPG上的单层中形成有序的2D结构，但是具有不同的堆积模式。NBI–（TAA）₂不会形成有序的3D结构，从而产生非晶薄膜，而NBI–TAA–Oc的薄膜则是高度结晶的。DFT计算预测NBI–TAA–Oc和NBI–（TAA）₂的电离电势（IP）为5.22 eV和5.18 eV以及-3.25 eV和-3.22 eV的电子亲和力值（EA）。这些结果与循环伏安法数据一致，该数据可产生相似的IP值（5.20 eV和5.19 eV）和某种程度上的EA值（−3.80 eV和−3.83 eV）。根据这些数据判断，两种半导体都应表现出双极性行为。实际上，NBI–TAA–Oc是双极性的，在场效应晶体管中显示的空穴迁移率和电子迁移率分别为4.5×10 ^-5 cm ² /（V s）和2.6×10 ^-4 cm ² /（V s）。配置。NBI–（TAA）₂不是双极性的，仅在p通道配置中会产生场效应。这种不同的行为是根据结构因素合理化的。