可溶液加工p-n多臂结构共轭分子的设计合成与应用
收稿日期: 2014-05-10
修回日期: 2014-06-01
网络出版日期: 2014-06-16
基金资助
国家重点基础研究发展计划（973计划，No. 2014CB648300）、国家自然科学基金（Nos. 20904024，51173081，61136003，61106036）、江苏省自然科学基金（No. BK20130037，BK2011760）、教育部新世纪优秀人才（No. NCET-13-0872）、教育部博士点基金博导类（No. 20133223110008）、教育部创新团队（No. IRT1148）、江苏高校优势学科建设工程（PAPD）、江苏省六大人才高峰（No. 2012XCL035）和江苏省“青蓝工程”资助项目.
Solution-Processable Star-Shaped Conjugated Molecules with Multiple p-n Branches：Synthesis and Photovoltaic Properties
Received date: 2014-05-10
Revised date: 2014-06-01
Online published: 2014-06-16
Supported by
Project supported by the National Key Basic Research Program of China (973 Program, No. 2014CB648300), the National Natural Science Foundation of China (Nos. 20904024, 51173081, 61136003, 61106036), the Natural Science Foundation of Jiangsu Province (Nos. BK20130037, BK2011760), the Ministry of Education of China (Nos. NCET-13-0872, 20133223110008, IRT1148), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), the Six Talent Plan (No. 2012XCL035), the Qing Lan Project of Jiangsu Province.
范晓春 , 王芳 , 李祥春 , 陈垚 , 赖文勇 , 黄维 . 可溶液加工p-n多臂结构共轭分子的设计合成与应用[J]. 有机化学, 2014 , 34(10) : 2027 -2034 . DOI: 10.6023/cjoc201405016
Well-defined π conjugated star-shaped molecules have attracted much research interest in the field of organic electronics, due to their good monodispersity, high purity, excellent reproducibility, facile functionalization, interesting two/three-dimensional architecture and potential intriguing isotropic optoelectronic properties. Here two new p-n type star-shaped conjugated molecules, S1 and S2, with phenylcarbazole as core and benzothiodiazole derivatives as arms, were designed and synthesized. They are readily soluble in common organic solvents. The structures of the intermediates and resulting molecules were adequately confirmed by 1H NMR, 13C NMR, MALDI-TOF, and elemental analysis. S1 and S2 exhibited good thermal stability according to thermal gravimetric analysis; cyclic voltammetry revealed low-lying HOMO and LUMO energy levels as well as narrow band gaps. The HOMO/LUMO energy levels and band gaps could be facilely modulated by varying the content and sequence of p and/or n type moieties. With incorporating 3-hexylthiophene π bridge unit, S2 film shows a broad absorption band from 300 nm to 650 nm in films with absorption edge red-shifted by ca. 38 nm in comparison with that of S1. Additionally, S2 possessed amorphous properties, while S1 exhibited crystalline properties in powder. Density functional theory (DFT) calculation was also conducted to further understand the electronic properties. Solution-processed organic solar cells based on a blend of S1 and PC70BM (1:3, w/w) exhibited power conversion efficiency (PCE) of 0.34% with a short circuit current density (Jsc) of 1.5 mA/cm2 and an open circuit voltage (Voc) of 0.83 V under the illumination of AM1.5, 100 mW/cm2. Improved performance was achieved for S2 with PCE of 0.5%, Jsc of 1.85 mA/cm2, and a high Voc of 1.0 V under identical conditions.
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