4-bromo-N-hexyl-phthalimide | 299963-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-bromo-N-hexyl-phthalimide
• 英文别名: 5-Bromo-2-hexylisoindole-1,3-dione
• CAS: 299963-46-5
• 化学式: C₁₄H₁₆BrNO₂
• 分子量: 310.191
• InChiKey: ATPNNTQMUDOFML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  噻吩并[3,2-b]噻吩 、 4-bromo-N-hexyl-phthalimide 在 potassium carbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以14%的产率得到
  参考文献：
  名称：

  通过直接（杂）芳基化反应合成与有机电子相关的芳族酰亚胺四聚物†

  摘要：

  我们报告了六种四聚体化合物，这些化合物是通过基于邻苯二甲酰亚胺，萘二甲酰亚胺和per二酰亚胺端基的直接（杂）芳基化方法与稠合噻吩核合成的。使用一组标准的反应条件，可以同时取代噻吩结构单元的2和3位。使用1 H和13 C NMR光谱，元素分析，循环伏安法以及光吸收和发射光谱对每种四聚体进行充分表征和分析。这项工作证明了一种用于有机电子应用的合成复杂四聚体材料的有效方法。

  DOI：

  10.1039/c9nj01553a
• 作为产物：
  描述：

  4-溴邻苯二甲酸酐 、 正己胺 以 甲苯 为溶剂， 反应 18.0h， 以99%的产率得到4-bromo-N-hexyl-phthalimide
  参考文献：
  名称：

  推挽大环：具有成对的线性共轭或交叉共轭途径的供体-受体化合物

  摘要：

  二维π系统目前在功能性有机分子的设计中受到关注，它在有机电子，单分子器件和传感中的应用表现出独特的性能。在这里，我们描述“推挽大环”的合成和表征：通过一对（匹配的）共轭桥连接的富电子和贫电子部分。我们已经开发出了一种由两部分组成的大环化策略，可以使这些结构以与无环供体-桥-受体系统相当的效率进行合成。用化合物两者交叉偶联（米亚苯基）和线性缀合（2,5-噻吩）桥梁已制备。如所期望的，化合物经历激发到局部激发态，随后是来自电荷转移态的荧光。该米基于亚苯基的系统表现出较慢的电荷复合速率，这可能是由于通过交叉共轭桥的电子耦合降低所致。有趣的是，配对线性共轭的2,5-噻吩桥也会减慢电荷重组。前沿分子轨道的DFT计算表明，对于这些对称的大环结构，直接的HOMO-LUMO跃迁极化正交于电荷转移轴，从而减少了电子耦合。我们认为，推挽式大环设计可能对工程化功能前沿分子轨道对称性有用。

  DOI：

  10.1021/jo2026004

文献信息

• Development of simple hole-transporting materials for perovskite solar cells
  作者：Andrew M. Namespetra、Arthur D. Hendsbee、Gregory C. Welch、Ian G. Hill

  DOI：10.1139/cjc-2015-0427

  日期：2016.4

  Three low-cost propeller-shaped small molecules based on a triphenylamine core and the high-performance donor molecule 7,7′-[4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl]bis[6-fluoro-4-(5′-hexyl-[2,2′-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazole] (DTS(FBTTh₂)₂) were investigated as hole-transporting materials in perovskite solar cells. Each hole-transporting material was designed with highly modular side arms, allowing for different bandgaps and thin-film properties while maintaining a consistent binding energy of the highest occupied molecular orbitals to facilitate hole extraction from the perovskite active layer. Perovskite solar cell devices were fabricated with each of the three triphenylamine-based hole-transporting materials and DTS(FBTTh₂)₂ and were compared to devices with 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (spiro-OMeTAD) hole-transporting layers. Each of our triphenylamine hole-transporting materials and DTS(FBTTh₂)₂ displayed surface morphologies that were considerably rougher than that of spiro-OMeTAD; a factor that may contribute to lower device performance. It was found that using inert, insulating polymers as additives with DTS(FBTTh₂)₂ reduced the surface roughness, resulting in devices with higher photocurrents.

  基于三苯胺核心和高性能给体分子7,7′-[4,4-双(2-乙基己基)-4H-硅杂[3,2-b:4,5-b′]噻吩-2,6-二基]双[6-氟-4-(5′-己基-[2,2′-联噻吩]-5-基)苯并[c][1,2,5]噻二唑] (DTS(FBTTh₂)₂) 为基础的三种低成本螺旋桨状小分子被研究作为钙钛矿太阳能电池中的传孔材料。每种传孔材料均设计有高度模块化的侧臂，可实现不同的带隙和薄膜性能，同时保持最高占据分子轨道的一致结合能，以促进从钙钛矿活性层中提取空穴。使用每种基于三苯胺的传孔材料和DTS(FBTTh₂)₂制备了钙钛矿太阳能电池器件，并与具有2,2′,7,7′-四(对-甲氧基苯胺基)-9,9′-螺联苯芴 (spiro-OMeTAD) 传孔层的器件进行了比较。我们的每种三苯胺传孔材料和DTS(FBTTh₂)₂显示出明显比spiro-OMeTAD更粗糙的表面形态，这可能导致器件性能较低。研究发现，在DTS(FBTTh₂)₂中使用惰性、绝缘聚合物作为添加剂可减少表面粗糙度，从而产生具有更高光电流的器件。
• Utility of a heterogeneous palladium catalyst for the synthesis of a molecular semiconductor via Stille, Suzuki, and direct heteroarylation cross-coupling reactions
  作者：Seth M. McAfee、Jenny S. J. McCahill、Casper M. Macaulay、Arthur D. Hendsbee、Gregory C. Welch

  DOI：10.1039/c5ra02468d

  日期：——

  commercially available silica-supported heterogeneous catalyst SiliaCat® DPP-Pd has proven to be highly active, robust, and reusable for the synthesis of a thiophene–phthalimide-based molecular semiconductor under microwave-irradiation reaction conditions. A Stille reaction protocol demonstrated that SiliaCat® DPP-Pd outperformed well-known homogeneous catalysts, Pd(PPh3)4 and Pd(PPh3)2Cl2, in terms of

  市售二氧化硅负载的非均相催化剂Silia猫®DPP-钯已被证明是高活性的，强大的，且可重复使用微波照射反应条件下的基于噻吩邻苯二甲酰亚胺分子半导体的合成。甲Stille反应协议证明Silia猫®DPP-钯优于公知的均相催化剂，的Pd（PPh 3）4和Pd（PPH 3）2氯2，在性能和催化剂负载量而言，同时还表现出耐受性的环境反应条件和产品形成的两倍可回收性。对于Silia建立成功猫®DPP-Pd催化的Stille反应通过微波辐射扩展到优化Suzuki偶联和直接杂芳化协议。值得注意的是，直接与杂芳基化Silia猫®DPP-钯表现出优异的选择性和扰动的均耦合芳基溴化物，两个侧反应已知困扰这种类型的交叉偶联反应的形成。
• Development of low band gap molecular donors with phthalimide terminal groups for use in solution processed organic solar cells
  作者：Ronan R. San Juan、Abby-Jo Payne、Gregory C. Welch、Ala’a F. Eftaiha

  DOI：10.1016/j.dyepig.2016.05.015

  日期：2016.9

  narrow bandgap ‘donor’ small molecule semiconductors are reported. The new compounds are based upon the popular DTS(FBT-Th2-Hexyl)2 donor molecule which has a D2-A-D1-A-D2 architecture with D1 = dithienosilole (DTS), A = 2-fluorobenzothiadiazole (FBT), and D2 = hexyl-bithiophene (Th2-Hexyl). We have replaced the D2 hexyl-bithiophene unit with electron withdrawing phthalimide units. The new materials

  报道了两种新型窄带隙“供体”小分子半导体的合成和表征。这些新化合物基于流行的DTS（FBT-Th 2-己基）2供体分子，该分子具有D2-A-D1-A-D2结构，其中D1 =双硫杂硅醇（DTS），A = 2-氟苯并噻二唑（FBT）， D2 =己基联噻吩（Th 2-己基）。我们已经用吸电子邻苯二甲酰亚胺单元取代了D2己基-联噻吩单元。结合理论计算，紫外可见光谱，循环伏安法和热分析对新材料进行了表征。邻苯二甲酰亚胺取代导致最高占据分子轨道能级的总体稳定，并且偶极矩和有机溶剂溶解度均增加。与PC 61 BM配对时，有机太阳能电池的功率转换效率出奇地低。对活性层形态的研究表明，存在较大的相分离域，表明邻苯二甲酰亚胺取代使供体分子与富勒烯受体不混溶。
• Solution-Processed Organic Solar Cells with Power Conversion Efficiencies of 2.5% using Benzothiadiazole/Imide-Based Acceptors
  作者：Jason T. Bloking、Xu Han、Andrew T. Higgs、John P. Kastrop、Laxman Pandey、Joseph E. Norton、Chad Risko、Cynthia E. Chen、Jean-Luc Brédas、Michael D. McGehee、Alan Sellinger

  DOI：10.1021/cm203111k

  日期：2011.12.27

  A new series of electron-deficient molecules based on a central benzothiadiazole moiety flanked with vinylimides has been synthesized via Heck chemistry and used in solution-processed organic photovoltaics (OPV). Two new compounds, 4,7-bis(4-(N-hexyl-phthalimide)vinyl)benzo[c]1,2,5-thiadiazole (PI-BT) and 4,7-bis(4-(N-hexylnaphthalimide)vinyl)benzo[c]1,2,5-thiadiazole (NI-BT), show significantly different behaviors in bulk heterojunction (BHJ) solar cells using poly(3-hexylthiophene) (P3HT) as the electron donor. Two-dimensional grazing incidence X-ray scattering (2D GIXS) experiments demonstrate that PI-BT shows significant crystallization in spin-coated thin films, whereas 02 NI-BT does not. Density functional theory (DFT) calculations predict that while PI-BT maintains a planar structure in the ground state, steric interactions cause a twist in the NI-BT (.) E molecule, likely preventing significant crystallization. In BHJ solar cells with P3HT as donor, PI-BT devices achieved a large open-circuit voltage of 0.96 V and a maximum device power-conversion efficiency of 2.54%, whereas NI-BT containing devices only achieved 0.1% power-conversion efficiency.
• Thiophene vs thiazole: Effect of the π-connector on the properties of phthalimide end-capped diketopyrrolopyrrole based molecular acceptors for organic photovoltaics
  作者：Pierre Josse、Patricia Chávez、Chloé Dindault、Clément Dalinot、Seth M. McAfee、Sylvie Dabos-Seignon、Denis Tondelier、Gregory Welch、Philippe Blanchard、Nicolas Leclerc、Clément Cabanetos

  DOI：10.1016/j.dyepig.2016.10.046

  日期：2017.2

  Two phthalimide end-capped diketopyrrolopyrrole based non-fullerene derivatives distinguished by the nature of the pi-conjugated connector namely a thiophene or a thiazole ring were synthesized via direct arylation and evaluated as electron acceptor materials in air-processed inverted organic solar cells. It turns out that this simple chemical modification significantly impacts the energetics, the charge transport properties and consequgntly the photovoltaic performances. (C) 2016 Elsevier Ltd. All rights reserved.