A Lewis acid-base chemistry approach towards narrow bandgap dye molecules
文献类型：期刊论文
| 作者 | Huang, Jianhua1; Li, Yongchun1; Wang, Yike1; Meng, Huifeng1; Yan, Dong2; Jiang, Bowen1; Wei, Zhanhua1; Zhan, Chuanlang2 |
| 刊名 | DYES AND PIGMENTS
 |
| 出版日期 | 2018-06-01 |
| 卷号 | 153页码:1-9 |
| ISSN号 | 0143-7208 |
| DOI | 10.1016/j.dyepig.2018.02.003 |
| 英文摘要 | Although it usually involves troublesome and time-consuming synthesis work, molecular structure tailoring has been the mainstream tool to adjust the optical absorption and bandgap of organic semiconductors. Herein, we provided a convenient and feasible method to prepare narrow bandgap small-molecule semiconductors by Lewis acid-base chemistry and the optical absorption was adjusted by the stoichiometry of Lewis add-base reactions. In this work, three pyridine capped diketopyrrolopyrrole (DPP) molecules, i.e., DPPPy-Ph-F, DPPPy-Ph-3F, and DPPPy-Py-F, with medium bandgap were synthesized to coordinate with Lewis acid of B(C6F5)(3) (BCF). By coordinating with BCF, as demonstrated by H-1, F-19, and B-11 NMR spectra, the bandgaps of these DPP molecules were depressed largely. For DPPPy-Ph-F, with two pyridine units flanking symmetrically, 2 eq of BCF converted the two pyridine nitrogens stoichiometrically to Lewis acid adducts, along with absorption bands red-shifted and bandgap depressed (1.89 vs. 1.80 eV). For DPPPy-Ph-3F, with two pyridine units flanked and trifluorobenzene capped, adding 2 eq of BCF was unable to convert the two pyridine nitrogens to BCF adducts completely, due to the strong electron-drawing ability of trifluorobenzene substituent on pyridine, reducing its basicity. After adding excess BCF to coordinate with nitrogens, the bandgaps of DPPPy-Ph-3F also decreased from 1.92 eV to 1.84 eV. For DPPPy-Py-F, with four pyridine units flanked, 4 eq of BCF were required to bind the pyridine nitrogens. Accordingly, the red-shift of absorption bands and the depression of optical bandgaps (1.96 vs. 1.75 eV) for DPPPy-Py-F were most striking among the three molecules. |
| 语种 | 英语 |
| WOS记录号 | WOS:000429764800001 |
| 出版者 | ELSEVIER SCI LTD |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/45927]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Huang, Jianhua; Zhan, Chuanlang |
| 作者单位 | 1.Huaqiao Univ, Coll Mat Sci & Engn, Xiamen 361021, Peoples R China 2.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, CAS Key Lab Photochem, Beijing 100190, Peoples R China |
| 推荐引用方式 GB/T 7714 | Huang, Jianhua,Li, Yongchun,Wang, Yike,et al. A Lewis acid-base chemistry approach towards narrow bandgap dye molecules[J]. DYES AND PIGMENTS,2018,153:1-9. |
| APA | Huang, Jianhua.,Li, Yongchun.,Wang, Yike.,Meng, Huifeng.,Yan, Dong.,...&Zhan, Chuanlang.(2018).A Lewis acid-base chemistry approach towards narrow bandgap dye molecules.DYES AND PIGMENTS,153,1-9. |
| MLA | Huang, Jianhua,et al."A Lewis acid-base chemistry approach towards narrow bandgap dye molecules".DYES AND PIGMENTS 153(2018):1-9. |
入库方式： OAI收割
来源：化学研究所
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