4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzodithiophene-2,6-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzodithiophene-2,6-carbaldehyde
• 英文别名: 4,8-bis(5-(2-ethylhexyl)thienyl-2)-benzodithiophene-2,6-dicarbaldehyde；4,8-Bis(5(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene2,6-dicarbaldehyde；4,8-bis[5-(2-ethylhexyl)thiophen-2-yl]thieno[2,3-f][1]benzothiole-2,6-dicarbaldehyde
• 化学式: C₃₆H₄₂O₂S₄
• 分子量: 634.992
• InChiKey: UCUFHDPOVJDGND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.72
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  对氨基苯乙腈 、 4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzodithiophene-2,6-carbaldehyde 在 四丁基氢氧化铵 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以71%的产率得到
  参考文献：
  名称：

  A new organic far-red mechanofluorochromic compound derived from cyano-substituted diarylethene

  摘要：

  A new cyano-substituted diarylethene derivative (R-NH2) with reversible far-red mechanofluorochromic property was synthesized and confirmed by standard spectroscopic methods. To the best of our knowledge, the 684 nm red-shifted wavelength of the ground R-NH2 is the longest wavelength that has appeared in the literature. The mechanofluorochromic mechanism was investigated by small and wide-angle X-ray scattering and was ascribed to the destruction of crystalline structure. More in-depth study by infrared spectra and time-resolved emission-decay behaviors showed that the changes of C H out-of-plane bending vibrations in aryl group of the compound and the obvious increase of fluorescence lifetime might be the fundamental reasons. The synthetic strategy reported here can be extended to prepare more and more long-wavelength emission mechanofluorochromic materials, which can broaden the scope of application of such materials and for thoroughly understanding the mechanofluorochromic mechanism. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.066
• 作为产物：
  描述：

  2-(2-乙基己基)噻吩 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 7.75h， 生成 4,8-bis[5-(2-ethylhexyl)-2-thienyl]benzodithiophene-2,6-carbaldehyde
  参考文献：
  名称：

  一种基于苯并[1,2-b:4,5-b’]二噻吩的化合物及其制备方法

  摘要：

  本发明提供了一种基于苯并[1,2‑b:4,5‑b']二噻吩的化合物，具有如式(Ⅰ)所示的结构，其中，R1为‑CnH2n+1，且R2为‑Cn+2H2n+5，n选自1～20的偶数。本发明还提供了一种基于苯并[1,2‑b:4,5‑b']二噻吩的化合物的制备方法。本发明提供的化合物体系中，π电子有更大离域范围，能够使分子间更好地π‑π堆叠，有利于电荷的传输，能够有效提高基于该化合物有机小分子太阳能电池的开路电压及光电转换效率。而且制备方法简单高效，产率高。

  公开号：

  CN111606921A

文献信息

• Facile Preparation of Water Dispersible Red Fluorescent Organic Nanoparticles for Cell Imaging
  作者：Miao Luo

  DOI：10.5012/bkcs.2014.35.6.1732

  日期：2014.6.20

  Red fluorescent organic nanopaticles (FONs) based on a diarylacrylonitrile derivative conjugated molecule were facilely prepared by surfactant modification. Such red FONs showed excellent water solubility and biocompatibility, making them promising for cell imaging applications.

  基于二芳基丙烯腈衍生物的红色荧光有机纳米颗粒（FONs）通过表面活性剂改性简单制备而成。这些红色FONs具有优良的水溶性和生物相容性，使其在细胞成像应用中展现出良好的前景。
• Series of Quinoidal Methyl-Dioxocyano-Pyridine Based π-Extended Narrow-Bandgap Oligomers for Solution-Processed Small-Molecule Organic Solar Cells
  作者：Ailing Tang、Chuanlang Zhan、Jiannian Yao

  DOI：10.1021/acs.chemmater.5b01350

  日期：2015.7.14

  Small molecules with narrow bandgap of <1.6 eV can harvest the visible and near-infrared solar photons. In this Article, we report a new method to achieve narrow bandgap small molecule donors by using electron-deficient quinoidal methyl-dioxocyano-pyridine (MDP) to induce possible quinoidal resonance structure along the conjugated A−π–D−π–A backbone. Practically, two MDP moieties are covalently linked onto an electron-rich benzodithiophene (BDT) through the oligothiophene (0T–5T) π-bridge. The affording small molecules, namely, nTBM, exhibit broad and strong absorption bands covering the visible and near-infrared region from 400 to 870 nm. The estimated optical bandgap is down to 1.4 eV. The narrow bandgap is associated with the low-lying lowest unoccupied molecular orbital (LUMO) energy level (about −3.7 eV) and the high-lying highest occupied molecular orbital (HOMO) energy level (around −5.1 eV). Density-functional theory calculations reveal that the HOMO and LUMO energy levels, with the increase of the size of the oligothiophene bridge, become localizations in different moieties, i.e., the central electron-donating and the terminal electron-withdrawing units, respectively, which provides necessary driving force for the delocalization of the excited electrons and formation of the quinoidal resonance structure. The quinoidal structure enhances the photoinduced intramolecular charge-transfer, leading to the absorbance enhancement of the low-energy absorption band. With the increase of the size of the oligothiophene from 0 to 5 thienyl units and the change of the direction of the alkyl chains on the bridged thiophene from “outward” to “inward”, the crystalline nature, fibril length, and phase size of the blend films as well as the cell performance are all fine-tuned, also. With the “inward” alkyl chains, the terthiophene bridged molecule is amorphous, while the pentathiophene bridged one is relatively crystalline. Both molecules form nanoscale interpenetrating networks with a phase size of 15–20 nm when blended with PC71BM, showing the higher hole mobility and promising electric performance.

  窄带隙<1.6 eV的小分子可以收获可见光和近红外太阳光子。在本文中，我们报告了一种获得窄带隙小分子供体的新方法，通过使用缺电子的醌型甲基二氧氰基吡啶（MDP）沿着共轭的A−π–D−π–A主链诱导可能的醌型共振结构。实际上，两个 MDP 部分通过低聚噻吩 (0T–5T) π 桥共价连接到富电子苯并二噻吩 (BDT) 上。这种小分子，即 nTBM，具有覆盖 400 至 870 nm 可见光和近红外区域的宽而强的吸收带。估计光学带隙低至 1.4 eV。窄带隙与低位最低未占分子轨道（LUMO）能级（约-3.7 eV）和高位最高占据分子轨道（HOMO）能级（约-5.1 eV）相关。密度泛函理论计算表明，随着低聚噻吩桥尺寸的增加，HOMO和LUMO能级分别定位在不同的部分，即中心给电子单元和末端吸电子单元，这提供了激发电子离域和形成醌型共振结构的必要驱动力。醌型结构增强了光诱导分子内电荷转移，导致低能吸收带的吸光度增强。随着低聚噻吩尺寸从0个增加到5个噻吩基单元以及桥联噻吩上烷基链方向从“向外”到“向内”的变化，低聚噻吩的结晶性质、原纤长度和相尺寸都发生了变化。混合薄膜以及电池性能也都经过微调。由于烷基链“向内”，三噻吩桥联分子是无定形的，而五噻吩桥联分子则相对结晶。当与 PC71BM 混合时，两种分子形成相尺寸为 15-20 nm 的纳米级互穿网络，表现出更高的空穴迁移率和良好的电性能。
• 一种基于苯并[1,2-b:4,5-b’]二噻吩的化合物及其制备方法
  申请人：河南省科学院化学研究所有限公司

  公开号：CN111606921A

  公开（公告）日：2020-09-01

  本发明提供了一种基于苯并[1,2‑b:4,5‑b']二噻吩的化合物，具有如式(Ⅰ)所示的结构，其中，R1为‑CnH2n+1，且R2为‑Cn+2H2n+5，n选自1～20的偶数。本发明还提供了一种基于苯并[1,2‑b:4,5‑b']二噻吩的化合物的制备方法。本发明提供的化合物体系中，π电子有更大离域范围，能够使分子间更好地π‑π堆叠，有利于电荷的传输，能够有效提高基于该化合物有机小分子太阳能电池的开路电压及光电转换效率。而且制备方法简单高效，产率高。
• Facile preparation of water dispersible red fluorescent organic nanoparticles and their cell imaging applications
  作者：Xiqi Zhang、Xiaoyong Zhang、Bin Yang、Yaling Zhang、Yen Wei

  DOI：10.1016/j.tet.2014.04.010

  日期：2014.6

  Red fluorescent organic nanoparticles (FONs) based on a cyano-substituted diarylethylene and tetraphenylethene derivative conjugated molecule (R-TPE) were facilely prepared via surfactant modification with lecithin for the first time. The obtained R-TPE-LEC FONs were characterized by a series of techniques including fluorescence and UV spectroscopy, Fourier transform infrared spectroscopy, and transmission electron microscopy. Biocompatibility evaluation and cell uptake behavior of R-TPE-LEC FONs were further investigated to explore their potential biomedical application. We demonstrated that such red FONs exhibit anti-aggregation-caused quenching property, broad excitation wavelength, high water dispersibility, uniform morphology (40-60 nm), and excellent biocompatibility, making them promising for cell imaging application. (C) 2014 Elsevier Ltd. All rights reserved.
• A new organic far-red mechanofluorochromic compound derived from cyano-substituted diarylethene
  作者：Xiqi Zhang、Zhiyong Ma、Meiying Liu、Xiaoyong Zhang、Xinru Jia、Yen Wei

  DOI：10.1016/j.tet.2013.10.066

  日期：2013.12

  A new cyano-substituted diarylethene derivative (R-NH2) with reversible far-red mechanofluorochromic property was synthesized and confirmed by standard spectroscopic methods. To the best of our knowledge, the 684 nm red-shifted wavelength of the ground R-NH2 is the longest wavelength that has appeared in the literature. The mechanofluorochromic mechanism was investigated by small and wide-angle X-ray scattering and was ascribed to the destruction of crystalline structure. More in-depth study by infrared spectra and time-resolved emission-decay behaviors showed that the changes of C H out-of-plane bending vibrations in aryl group of the compound and the obvious increase of fluorescence lifetime might be the fundamental reasons. The synthetic strategy reported here can be extended to prepare more and more long-wavelength emission mechanofluorochromic materials, which can broaden the scope of application of such materials and for thoroughly understanding the mechanofluorochromic mechanism. (C) 2013 Elsevier Ltd. All rights reserved.