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首页> 外文期刊>Chemistry: A European journal >Combining high electron affinity and intramolecular charge transfer in 1,3-dithiole-nitrofluorene push-pull diads
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Combining high electron affinity and intramolecular charge transfer in 1,3-dithiole-nitrofluorene push-pull diads

机译：高电子亲和力和分子内电荷转移在1,3-二硫代-硝基芴推挽二元相结合

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摘要

Attaching electron-rich 1,3-dithiol-2-ylidene moieties to polynitrofluorene electron acceptors leads to the formation of highly conjugated compounds 6 to 11, which combine high electron affinity with a pronounced intramolecular charge transfer (ICT) that is manifested as an intense absorption band in their visible spectra. Such a rare combination of optical and electronic properties is beneficial for several applications in optoelectronics. Thus, incorporation of fluorene-dithiole derivative 6a into photoconductive films affords photothermoplastic storage media with dramatically increased photosensitivity in the ICT region. A wide structural variation of the dithiole and fluorene parts of the molecules reveals excellent correlation between the ICT energy and the reduction potential with the Hammett's parameters for the substituents. Although only a small solvatochromism of the ICT band was observed, heating the solution led to a pronounced blueshift, which was probably as a result of increased twisting around the C9 = C14 bond that links the fluorene and dithiole moieties. X-ray crystallographic analysis of 7a, 8a, 10a, 11a and 13a confirms an ICT interaction in the ground state of the molecules. The C9 = C14 double bond between the donor and acceptor is substantially elongated and its length increases as the donor character of the dithiole moiety is enhanced.
机译：将富含电子的1,3-二硫醇-2-亚甲基连接到聚硝基芴电子受体上会导致形成高度共轭的化合物6至11，这些化合物将高电子亲和力与明显的分子内电荷转移（ICT）结合在一起，表现为强烈的可见光谱中的吸收带。光学和电子特性的这种罕见组合对于光电子学中的多种应用是有益的。因此，将芴-二硫醇衍生物6a掺入光电导膜中提供了光热可塑性存储介质，其在ICT区域具有显着提高的光敏性。分子中二硫醇和芴部分的广泛结构变化揭示了ICT能量和还原电势与取代基的Hammett参数之间的极佳相关性。尽管仅观察到ICT波段很小的溶剂变色现象，但加热溶液会导致明显的蓝移，这可能是由于连接芴和二硫键部分的C9 = C14键周围扭曲增加的结果。 7a，8a，10a，11a和13a的X射线晶体学分析证实了分子基态中的ICT相互作用。供体和受体之间的C9 ＝ C14双键基本上被延长，并且其长度随着二硫醇部分的供体特性的增强而增加。

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