Synthesis, optical properties and charge transport characteristics of a series of novel thiophene-fused phenazine derivatives
Synthesis, optical properties and charge transport characteristics of a series of novel thiophene-fused phenazine derivatives
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DOI：
10.1039/c3tc30346b
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发表时间：
2013-05
影响因子：
6.4
通讯作者：
Yong‐Xin Xie;Takuya Fujimoto;S. Dalgleish;Yoshiaki Shuku;M. Matsushita;K. Awaga
中科院分区：
文献类型：
--
作者：
Yong‐Xin Xie;Takuya Fujimoto;S. Dalgleish;Yoshiaki Shuku;M. Matsushita;K. Awaga
通过二酮与二胺的简单缩合反应，合成了一系列四噻吩并吩嗪衍生物（t-TTP、l-TTP、m-TTP及其烷基取代衍生物）。这些衍生物的氧化还原电位、紫外-可见吸收光谱和荧光光谱受硫原子和烷基位置的显著影响。基于密度泛函理论的理论计算很好地再现了所观察到的电子性质。这些衍生物的X-射线分析表明，广泛的π-π相互作用和短的S-π-S接触。烷基取代的衍生物通过气相沉积提供高度结晶的薄膜，并显示出合理的场效应晶体管性能。这些材料的掺杂单晶的电导率也进行了研究，并显示了几个数量级的I2蒸气掺杂后的增加。这些晶体的π-π堆叠结构和导电性能表明，这些噻吩稠合吩嗪是有用的材料，用于有机电子学。
A series of tetrathienophenazine derivatives (t-TTP, l-TTP, m-TTP and their alkyl-substituted derivatives) have been synthesized via a simple condensation reaction between diketones and diamines. The redox potentials, UV-vis absorption spectra and fluorescence spectra of these derivatives are significantly affected by the positions of the sulfur atoms and the alkyl groups. The observed electronic properties were well reproduced by theoretical calculations based on density functional theory. X-ray analyses of these derivatives reveal extensive π–π interactions and short S⋯S contacts. The alkyl-substituted derivatives afford highly crystalline thin films by vapor deposition, and show reasonable field effect transistor performance. The conductivity of doped single crystals of these materials was also investigated, and showed an increase by several orders of magnitude upon I2 vapor doping. The π–π stacked structures of these crystals and conductive properties indicate that these thiophene-fused phenazines are useful materials for application in organic electronics.