Pushing Extended p-Quinodimethanes to the Limit: Stable Tetracyano-oligo(N-annulated perylene)quinodimethanes with Tunable Ground States
文献类型：会议论文
| 作者 | Zeng, Zebing; Ishida, Masatoshi; Zafra, Jose L.; Zhu, Xiaojian; Sung, Young Mo; Bao, Nina; Webster, Richard D.; Lee, Byung Sun; Li, Run-Wei; Zeng, Wangdong |
| 出版日期 | 2013 |
| 关键词 | OPEN-SHELL QUINOIDAL OLIGOTHIOPHENES ELECTRON-ACCEPTORS CLOSED-SHELL TETRACYANODIPHENOQUINODIMETHANE HYDROCARBONS AROMATICITY ABSORPTION CHEMISTRY ANALOGS |
| 卷号 | 135 |
| 期号 | 16 |
| DOI | 10.1021/ja402467y |
| 英文摘要 | p-Quinodimethane (p-QDM) is a fundamental building block for the design of pi-conjugated systems with low band gap and open-shell biradical character. However, synthesis of extended p-QDMs has usually suffered from their intrinsic high reactivity and poor solubility. In this work, benzannulation together with terminal cyano-substitution was demonstrated to be an efficient approach for the synthesis of a series of soluble and stable tetracyano-oligo(N-annulated perylene)quinodirnethanes nPer-CN (n = 1-6), with the longest molecule having 12 para-linked benzenoid rings! The geometry and electronic structures of these oligomers were investigated by steady-state and transient absorption spectroscopy, nuclear magnetic resonance, electron spin resonance, superconducting quantum interference device, and FT Raman spectroscopy assisted by density functional theory calculations. They showed tunable ground states, varying from a closed-shell quinoidal structure for monomer, to a singlet biradical for dimer, trimer, and tetramer, and to a triplet biradical for pentamer and hexamer. Large two-photon absorption cross-section values were observed in the near-infrared range, which also exhibited a clear chain-length dependence. |
| 学科主题 | Chemistry |
| ISSN号 | 0002-7863 |
| 源URL | [http://ir.nimte.ac.cn/handle/174433/23623]  |
| 专题 | 会议专题 会议专题_会议论文 |
| 推荐引用方式 GB/T 7714 | Zeng, Zebing,Ishida, Masatoshi,Zafra, Jose L.,et al. Pushing Extended p-Quinodimethanes to the Limit: Stable Tetracyano-oligo(N-annulated perylene)quinodimethanes with Tunable Ground States[C]. 见:. |
入库方式： OAI收割
来源：宁波材料技术与工程研究所
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