bis(trimethylstannyl)oligothiopheneand 1-(2-methoxyethoxyl)-7-bromo-PDI | 1356240-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: bis(trimethylstannyl)oligothiopheneand 1-(2-methoxyethoxyl)-7-bromo-PDI
• 英文别名: 1-Bromo-7-(2-methoxyethoxyl)perylene diimide；11-bromo-7,18-bis(2-ethylhexyl)-22-(2-methoxyethoxy)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• CAS: 1356240-55-5
• 化学式: C₄₃H₄₇BrN₂O₆
• 分子量: 767.76
• InChiKey: OPQPVWUSMBHZAK-UHFFFAOYSA-N

物化性质

• 沸点：
  851.8±65.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(trimethylstannyl)oligothiopheneand 1-(2-methoxyethoxyl)-7-bromo-PDI 在 溴 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  Orientation of bromination in bay-region of perylene diimides

  摘要：

  We found that the entering position of the bromination in the bay-region (e.g., 1,6,7,12-positions) was precisely determined by the orientation director(s), either individually or cooperatively. In particular, a combination of two directors shows precisely positioning for the third entering bromo with an effect of '1+1>2'. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.035
• 作为产物：
  描述：

  5-bromo-2,9-bis(2-ethylhexyl)-anthra [2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone 在 溴 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 bis(trimethylstannyl)oligothiopheneand 1-(2-methoxyethoxyl)-7-bromo-PDI
  参考文献：
  名称：

  Orientation of bromination in bay-region of perylene diimides

  摘要：

  We found that the entering position of the bromination in the bay-region (e.g., 1,6,7,12-positions) was precisely determined by the orientation director(s), either individually or cooperatively. In particular, a combination of two directors shows precisely positioning for the third entering bromo with an effect of '1+1>2'. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.035

文献信息

• 五元杂环衍生物桥联的苝二酰亚胺二聚体、其 制备方法及其在有机光伏器件中的应用
  申请人：中国科学院化学研究所

  公开号：CN104045657B

  公开（公告）日：2017-07-21

  本发明提供了一种1,1‑二烷氧基取代的不对称苝二酰亚胺二聚体，该苝二酰亚胺二聚体为溶液可加工的电子受体型有机小分子。本发明还提供了一种合成这类不对称取代的苝二酰亚胺二聚体的方法。同时，使用该不对称取代的苝二酰亚胺二聚体为受体，与P3HT等电子给体型聚合物组合，制备了有机太阳能电池，取得了很高的光电转换效率，为光伏领域的研究提供了一个方向。
• Synthesis and photovoltaic properties of low bandgap dimeric perylene diimide based non-fullerene acceptors
  作者：Xin Zhang、Jiannian Yao、Chuanlang Zhan

  DOI：10.1007/s11426-015-5485-8

  日期：2016.2

  Non-fullerene organic acceptors have attracted increasing attention in recent years. One of the challenges in the synthesis of non-fullerene organic acceptors is to tune the absorption spectrum and molecular frontier orbitals, affording low bandgap molecules with improved absorption of the near-infrared solar photons. In this paper, we present the synthesis, optoelectronic and photovoltaic properties of a series of dimeric perylene diimide (PDI) based non-fullerene acceptors. These PDI dimers are bridged by oligothiophene (T) from 1T to 6T. With the increase of the oligothienyl size, the highest occupied molecular orbital (HOMO) energy is raised from −5.65 to −5.10 eV, while that of the lowest unoccupied molecular orbit (LUMO) is kept constant at −3.84 eV, affording narrow bandgap from 1.81 to 1.26 eV. The absorption from the oligothiophene occurs between 350 and 500 nm, which is complementary to that from its bridged PDI units, leading to a wide spectral coverage from 350 to 850 nm. The optimal dihedral angle between the bridged two perylene planes is dependent on the oligothienyl size, varying from 5° to 30°. The solubility of the dimers depends on the oligothienyl size and can be tuned by the alkyl chains on the bridged thienyl units. The possible applications as the solution-processable non-fullerene organic acceptor is primarily studied using commercial P3HT as the blend donor. The photovoltaic results indicate that 1T, 4T and 6T all yield a higher efficiency of ∼1.2%, whereas 2T, 3T and 5T all give a lower efficiency of <0.5%. The difference in the cell performance is related with the tradeoff between the differences of absorption, HOMO level and film-morphology between these dimers.

  近年来，非富勒烯有机受体越来越受到关注。合成非富勒烯有机受体的挑战之一是如何调整吸收光谱和分子前沿轨道，从而获得对近红外太阳光子有更好吸收的低带隙分子。在本文中，我们介绍了一系列基于二聚过二亚胺（PDI）的非富勒烯受体的合成、光电和光伏特性。这些 PDI 二聚体由 1T 到 6T 的低聚噻吩（T）桥接。随着低聚噻吩尺寸的增加，最高占位分子轨道（HOMO）的能量从 -5.65 eV 上升到 -5.10 eV，而最低未占位分子轨道（LUMO）的能量则保持在 -3.84 eV 不变，从而产生了从 1.81 到 1.26 eV 的窄带隙。低聚噻吩的吸收发生在 350 纳米到 500 纳米之间，与桥接 PDI 单元的吸收互补，从而产生了 350 纳米到 850 纳米的宽光谱覆盖范围。桥接的两个苝平面之间的最佳二面角取决于低聚噻吩的大小，从 5°到 30°不等。二聚体的溶解度取决于低聚噻吩基的大小，并可通过桥接噻吩基单元上的烷基链进行调整。我们主要以商用 P3HT 作为混合供体，研究了其作为可溶液加工的非富勒烯有机受体的应用可能性。光伏研究结果表明，1T、4T 和 6T 的效率均高于 1.2%，而 2T、3T 和 5T 的效率则低于 0.5%。电池性能的差异与这些二聚体之间的吸收、HOMO 水平和薄膜形态差异之间的权衡有关。
• Edge-to-face stacking non-fullerene small molecule acceptor for bulk heterojunction solar cells
  作者：Qichao Wu、Ling Li、Jiefeng Hai、Xin Zhang、Zhenhuan Lu、Jianwen Yang、Yongping Liu、Lingzhi Zhang、Chuanlang Zhan

  DOI：10.1016/j.dyepig.2016.04.040

  日期：2016.9

  Synthesis of a novel small molecule accepter with perylenediimide linked through thiophene ring with triphenylamine is described. Introducing thiophene unit leads to extending the molecular absorption spectrum to the range of 330 nm–700 nm. The molecule showed the lowest unoccupied molecular orbital level (LUMO) of −3.80 eV and the highest occupied molecular orbital level (HOMO) of −5.60 eV. The X-ray

  描述了一种新颖的小分子受体的合成，该受体具有通过噻吩环与三苯胺连接的per二酰亚胺。引入噻吩单元可将分子吸收光谱扩展到330 nm–700 nm范围。该分子显示出最低的未占据分子轨道能级（LUMO）为-3.80 eV，最高的未占据分子轨道能级（HOMO）为-5.60 eV。X射线衍射（XRD）光谱证实分子通过边对面的芳族相互作用在固相中自组装，并且在溶剂中添加1，8-二碘辛烷可以调节其堆积，从而改善结晶度和电子迁移率。以小分子为受体，PBDTTT-CT的聚合物为供体的固溶体异质结有机太阳能电池的最佳效率为1.92％。
• Facile synthesis of 1-bromo-7-alkoxyl perylene diimide dyes: toward unsymmetrical functionalizations at the 1,7-positions
  作者：Xin Zhang、Shufeng Pang、Zhigang Zhang、Xunlei Ding、Shanlin Zhang、Shenggui He、Chuanlang Zhan

  DOI：10.1016/j.tetlet.2011.12.080

  日期：2012.2

  In this Letter, we report a facile approach to synthesize unsymmetrical 1-bromo-7-alkoxyl perylene diimides by the nucleophilic substitution of one of the two 1.7-dibromo units with an alkyl alcohol using K2CO3 as the base. A further replacement of another bromo, for example, by using 4-hydroxylpyridine resulted in unsymmetrical functionalizations at the 1,7-positions. The optical properties of the unsymmetrical PDI derivative were reported and compared with those of the symmetrical derivative. (C) 2011 Elsevier Ltd. All rights reserved.