(5-(1,3-二氧杂烷-2-基)-4-己基噻吩-2-基)三丁基锡 | 1239242-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: (5-(1,3-二氧杂烷-2-基)-4-己基噻吩-2-基)三丁基锡
• 英文名称: (5-(1,3-dioxolan-2-yl)-4-hexylthiophen-2-yl)tributylstannane
• 英文别名: tributyl-[5-(1,3-dioxolan-2-yl)-4-hexylthiophen-2-yl]stannane
• CAS: 1239242-61-5
• 化学式: C₂₅H₄₆O₂SSn
• 分子量: 529.415
• InChiKey: SCCHFHVAHJLAIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-(1,3-二氧杂烷-2-基)-4-己基噻吩-2-基)三丁基锡 、 N-(4-((1E,3E)-4-(5-bromo-3-((1E,3E)-4-(4-(di-p-tolylamino)phenyl)buta-1,3-dienyl)-2-(octyloxy)phenyl)buta-1,3-dienyl)phenyl)-4-methyl-N-p-tolylbenzenamine 在 四(三苯基膦)钯 、 盐酸 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 以68%的产率得到5-(3,5-bis((1E,3E)-4-(4-(di-p-tolylamino)phenyl)buta-1,3-dienyl)-4-(octyloxy)phenyl)-3-hexylthiophene-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and photovoltaic properties of new branchlike organic dyes containing benzothiadiazole or triphenylamine-linked consecutive vinylenes units

  摘要：

  Two novel branchlike organic dyes (WD1 and FD1) based on 4,7-bis-(4-hexylthiophen-2-yl)benzo[1,2,5]thiadiazole (DTBT) and triphenylamine, containing vinylenes and consecutive vinylenes as pi-conjugated unit, respectively, were designed and synthesized for dye-sensitized solar cells (DSSCs). The photophysical, electrochemical and photovoltaic properties of the dyes were investigated. The introduction of consecutive vinylenes into two branches of the FD1 molecule leads to a remarkably red-shifted absorption and higher molar extinction coefficient compared with the reference dye D2. The DSSCs based on FD1 and WD1 dyes exhibited the power conversion efficiency of 7.04% and 2.18% under AM1.5G irradiation (100 mW/cm(2)). (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.01.009

文献信息

• Reversed Y-shape di-anchoring sensitizers for dye sensitized solar cells based on benzimidazole core
  作者：Mulu Berhe Desta、Sumit Chaurasia、Jiann T. Lin

  DOI：10.1016/j.dyepig.2017.01.068

  日期：2017.5

  Three new Y-shaped D-(π-A)2 di-anchoring organic dyes comprising an arylamine as the electron donor, 2-cyanoacrylic acid as electron acceptors and various 2,4,7-trisubstituted benzimidazole entity as the π-linkers/spacers, have been synthesized for dye-sensitized solar cells. The new dyes MD2 and MD3 show red-shifted absorption in solution spectra when compared with their congeners (8b and 9b) without

  三种新型Y形D-（π-A）2双锚定有机染料，包括芳胺作为电子供体，2-氰基丙烯酸作为电子受体和各种2,4,7-三取代的苯并咪唑实体作为π-连接剂/已经合成了用于染料敏化太阳能电池的间隔物。与没有给电子己氧基取代基的同类染料（8b和9b）相比，新染料MD2和MD3在溶液光谱中显示出红移吸收。苯并咪唑的N-烷基虽然有助于改善溶解度，但显然会导致苯并咪唑核心与连接至受体的共轭链段中相邻噻吩环之间的严重扭曲。N-烷基或与芳胺供体连接的苯环。对新染料进行了光物理和电化学测量以及理论计算。除电流电压扫描和入射光子至电子的转换效率（IPCE）外，还进行了电化学阻抗谱（EIS）研究。对于没有和有CDCA共吸附剂的DSSC，染料MD3分别显示出最高的光电能转化效率，分别为6.45％和6.69％。MD3比9b更好的电池性能可以归因于前者更好的光收集和更好的暗电流抑制。
• Tetraphenylethylene tethered phenothiazine-based double-anchored sensitizers for high performance dye-sensitized solar cells
  作者：Chun-Ting Li、Yi-Ling Kuo、CH. Pavan Kumar、Pei-Ting Huang、Jiann T. Lin

  DOI：10.1039/c9ta09025h

  日期：——

  The YL4 dye exhibits DSSC efficiencies of 10.87% (1 sun) and 27.54% (187 lux) due to effective double layered shelters (the dianchor skeleton and clogged TPE units) for blockade of dark current.

  YL4染料由于有效的双层遮蔽（双锚骨架和堵塞的TPE单元）以阻止暗电流，其DSSC效率为10.87％（1太阳）和27.54％（187勒克斯）。
• The unusual electronic structure of ambipolar dicyanovinyl-substituted diketopyrrolopyrrole derivatives
  作者：A. Riaño、P. Mayorga Burrezo、M. J. Mancheño、A. Timalsina、J. Smith、A. Facchetti、T. J. Marks、J. T. López Navarrete、J. L. Segura、J. Casado、R. Ponce Ortiz

  DOI：10.1039/c4tc00714j

  日期：——

  We have synthesized two novel dicyanovinylene-substituted DPP–oligothiophene semiconductors, DPP-4T-2DCV and 2DPP-6T-2DCV. In these materials, the combination of an extended oligothiophene conjugated skeleton with the strong electron-withdrawing DPP–dicyanovinylene groups results in semiconductors exhibiting ambipolar TFT response with reasonably balanced electron and hole mobilities of up to 0.16 cm2 V−1 s−1 and 0.02 cm2 V−1 s−1, respectively. Furthermore, no thermal annealing of the semiconductors is necessary to afford high mobility, making them ideal candidates for low cost fabrication of devices on inexpensive plastic foils. Analysis of the molecular and electronic structures by means of electronic and vibrational spectroscopy techniques, electrochemistry and DFT calculations highlights a unique electronic scenario in these semiconductors, where the external cyano groups are isolated from the π-conjugated core. The appearance of these unusual π-systems explains the similar electron mobilities recorded for both DPP-4T-2DCV and 2DPP-6T-2DCV, despite their different skeletal dimensions. Furthermore, it also supports the appearance of moderately balanced hole and electron mobilities in semiconductors with such large accumulation of acceptor units. Transient spectroscopy measurements indicate the appearance of triplet excited state species, which may be related to the semiconductors' low performances in OPVs, due to the intrusion of triplets in the carrier formation process.

  我们合成了两种新型双氰基乙烯基取代 DPP-寡噻吩半导体：DPP-4T-2DCV 和 2DPP-6T-2DCV。在这些材料中，延伸的低聚噻吩共轭骨架与强电子吸收性的 DPP-双氰基乙烯基团相结合，使半导体呈现伏极性 TFT 响应，电子和空穴迁移率相当平衡，分别高达 0.16 cm2 V-1 s-1 和 0.02 cm2 V-1 s-1。此外，无需对半导体进行热退火处理即可获得高迁移率，这使它们成为在廉价塑料薄膜上低成本制造器件的理想候选材料。通过电子和振动光谱技术、电化学和 DFT 计算对分子结构和电子结构进行分析，突出显示了这些半导体中独特的电子情况，即外部氰基与π共轭核心隔离。这些不寻常的 π 系统的出现解释了 DPP-4T-2DCV 和 2DPP-6T-2DCV 虽然骨架尺寸不同，但电子迁移率却相似的原因。此外，它还支持在具有如此大的受体单元积累的半导体中出现适度平衡的空穴和电子迁移率。瞬态光谱测量结果表明，在载流子形成过程中出现了三重激发态物种，这可能与半导体在 OPV 中的低性能有关。
• Organic sensitizers with a rigid dithienobenzotriazole-based spacer for high-performance dye-sensitized solar cells
  作者：Jen-Shyang Ni、Yi-Chi Yen、Jiann T. Lin

  DOI：10.1039/c6ta02275h

  日期：——

  ∼54 800 M−1 cm−1. The light-to-electricity conversion efficiencies of the dye-sensitized solar cells (DSSCs) ranged from 5.82 to 8.51% under simulated AM 1.5 G illumination. Upon addition of 5 mM of CDCA as a coadsorbent, the best performing cell displayed an efficiency of 9.10%, surpassing that of the N719-based standard cell (8.12%), and even achieved an efficiency of 10.56% under quarter sunlight illumination

  新型D–π–A型敏化剂（YC染料），包括芳基胺作为电子供体，二噻吩并[3'，2'：3,4; 2''，3''：5,6]苯并[1,2-合成了作为刚性π-共轭间隔基的d ] [1,2,3]三唑（DTBZ）和作为受体和锚点的2-氰基丙烯酸。该YC敏化剂显示的光的宽的吸收，从362纳米至550纳米，具有摩尔消光系数高达约54 800米-1厘米-1。在模拟AM 1.5 G照射下，染料敏化太阳能电池（DSSC）的光电转换效率在5.82％至8.51％的范围内。加入5 mM CDCA作为共吸附剂后，性能最佳的电池的效率为9.10％，超过了基于N719的标准电池的效率（8.12％），甚至在四分之一的日光照射下也达到了10.56％的效率。
• Efficient triphenylamine-based dyes featuring dual-role carbazole, fluorene and spirobifluorene moieties
  作者：Ping Shen、Yuhua Tang、Shenghui Jiang、Huajie Chen、Xiaoyan Zheng、Xueye Wang、Bin Zhao、Songting Tan

  DOI：10.1016/j.orgel.2010.10.016

  日期：2011.1

  Three triphenylamine-based organic dyes SD6, SD7, and SD8 containing the bulky dual-role moieties (fluorene, carbazole, and spirobifluorene) in the molecular frameworks were synthesized, characterized and applied in dye-sensitized solar cells (DSSCs). The effects of dual-role moieties of organic dyes on their photophysical, electrochemical, and photovoltaic properties have been investigated in detail. These dyes exhibit strong charge transfer absorption bands in the visible region. Their redox potential levels were estimated by cyclic voltammetry and found to suit well to the charge flow in DSSCs. Inserting the dual-role moieties as the secondary donor between the triphenylamine and thiophene units increased the electron density of the donor groups, therefore reduced the HOMO-LUMO band gaps. The combination of ultraviolet-visible (UV-vis) region broad absorption bands with fairly high extinction coefficients and appropriate redox properties observed in these triphenylamine-based dyes make them promising dyes for DSSCs. For a typical solar cell device based on dye SD6, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to similar to 73%, with a short-circuit photocurrent density (J(sc)) of 14.25 mA/cm(2), an open-circuit photovoltage (V-oc) of 0.70 V, and a fill factor (FF) of 0.705, which corresponds to a power conversion efficiency (PCE) of 7.03%. (C) 2010 Elsevier B. V. All rights reserved.