4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-hydroxy-3-cyclobutene-1,2-dione | 426227-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-hydroxy-3-cyclobutene-1,2-dione
• 英文别名: 3-[(1-butyl-3,3-dimethyl-1,3-dihydro-2H-indol-2-ylidene)methyl]-4-hydroxycyclobut-3-ene-1,2-dione；3-(1-butyl-3,3-dimethylindolin-2-ylidenemethyl)-4-hydroxycyclobut-3-ene-1,2-dione；3-[(1-Butyl-3,3-dimethylindol-2-ylidene)methyl]-4-hydroxycyclobut-3-ene-1,2-dione
• CAS: 426227-59-0
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: ROJHDKVOKNSXBS-UHFFFAOYSA-N

物化性质

• 沸点：
  410.8±55.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-hydroxy-3-cyclobutene-1,2-dione 在 喹啉 、 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 、 苯 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis and near-infrared absorption properties of linearly π-extended squarylium oligomers

  摘要：

  Linear squarylium oligomers bearing extended pi-conjugation systems were newly synthesized, and their near-infrared (NIR) light-absorbing properties were investigated. Replacement of the iodo substituent in a 5-iodinated indolino-squarylium dye to the 2-hydroxy-3,4-dioxocyclobut-1-en-1-yl functional group via the Pd-catalyzed cross-coupling with a tributylstannylsquarate followed by condensation with a quaternary indolium salt afforded the semi-squarylium-attached squarylium derivative, i.e., the squarylium dimer. The introduction of the semi-squarylium unit gave rise to a significant bathochromic shift towards the NIR region (lambda(abs) = 763 nm in CHCl(3) at 298 K). Starting from a 5,5'-diiodinated indolino-squarylium, the iterative extension of semi-squarylium units successfully yielded the linearly pi-extended trimer and pentamer, that showed absorption maxima at 862 and 940 nm in CHCl(3) at 298 K, respectively. Especially, the pentamer exhibited a considerably low optical band gap of 1.1 eV. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.12.005
• 作为产物：
  描述：

  3-butoxy-4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-cyclobutene-1,2-dione 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 以28%的产率得到4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-hydroxy-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Fluorescence properties of indolenine semi-squarylium dyes

  摘要：

  3-Butoxy-4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-cyclobut-1,2-dione exhibited the most intense florescence at fluorescence maxima 536 and 563 nm with fluorescence quantum yield 0.21 among any indolenine semi-squarylium dyes in the crystalline form due to the isolated dimer-type molecular packing and its suitable melting point. This compound showed aggregation-induced emission enhancement. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.089

文献信息

• 一系列含吲哚啉衍生物结构的不对称方酸菁小 分子及其应用
  申请人：四川大学

  公开号：CN104163785B

  公开（公告）日：2016-08-24

  本发明提供一系列新型不对称方酸菁小分子及其运用。通过在方酸四元环两端引入不同的富电芳香单元作为给体单元，设计合成了一系列低带隙的不对称方酸菁小分子光伏材料，其在可见及近红外光区具有强烈的吸收，吸收光谱覆盖400‑900 nm；其HOMO、LUMO与受体材料PCBM的能级匹配良好，获得高的开路电压，而且这类化合物都具有良好的溶解性和成膜性，使其可应用于低成本的溶液加工本体异质结有机太阳能电池器件。以不对称方酸小分子为给体材料的有机太阳能电池器件性能可达到：白光1.5 G（100 mw/cm2）照射下，开路电压（Voc）=0.72‑1.05V，短路电流（Jsc）=8.80‑12.67 mA/cm2，填充因子（FF）=0.38‑0.55，光电转化效率（PCE）=2.41‑6.10%。
• Two different donor subunits substituted unsymmetrical squaraines for solution-processed small molecule organic solar cells
  作者：Daobin Yang、Yan Jiao、Yan Huang、Taojun Zhuang、Lin Yang、Zhiyun Lu、Xuemei Pu、Hisahiro Sasabe、Junji Kido

  DOI：10.1016/j.orgel.2016.02.009

  日期：2016.5

  Two unsymmetrical squaraines (USQs) with different donor (D) subunits as photovoltaic materials, namely USQ-11 and USQ-12, were designed and synthesized to investigate the effect of different D subunits on the optoelectronic properties of USQs for the first time. The two USQs compounds were characterized for optical, electrochemical, quantum chemical and optoelectronic properties. By changing the two

  设计并合成了两个具有不同供体（D）亚基作为光伏材料的不对称偏方（USQ），即USQ-11和USQ-12，以首次研究不同D亚基对USQs光电性能的影响。这两种USQs化合物具有光学，电化学，量子化学和光电特性。通过将连接到方酸核心的两个不同的D亚基从2,3,3-三甲基吲哚变为2-甲基苯并噻唑，可以以0.07 eV的步进调整HOMO能级，并且可以实现非常不同的固态聚集（H-或通过紫外-可见吸收光谱在薄膜中观察到了J-聚集现象，这归因于其独特的空间效应和偶极矩。71 BM（1：5，wt％）的PCE（4.27％）比USQ-12 / PC 71 BM（2.78％）高得多。PCE大大增强应归因于同时提高的V oc，J sc和FF。
• Conformational effect of symmetrical squaraine dyes on the performance of dye-sensitized solar cells
  作者：Takeshi Maeda、Shohei Mineta、Hideki Fujiwara、Hidekazu Nakao、Shigeyuki Yagi、Hiroyuki Nakazumi

  DOI：10.1039/c2ta00883a

  日期：——

  A symmetrical squaraine dye altered to possess dicyanovinylene functionality on a carbonyl group of the cyclobutene core (SQM1a) was synthesized to elucidate the effects of the conformationally locked-in cis-like form ensured by the steric repulsion of dicyanovinylenes on the performance of dye-sensitized solar cells (DSSCs) through a comparison with an unsymmetrical analogue bearing one carboxy group (SQM1b) and a standard squaraine dye (MSQ). The FT-IR spectrum of the TiO2 thin film immersed in the dye solution suggested that the linkages between the dye and TiO2 were formed by both carboxy groups symmetrically incorporated on the π-conjugation of dyes. The symmetrical and conformationally locked structure of SQM1a brought about a decrease in the non-radiative decay rate, which may have been induced by suppression of the possible photoisomerization of squaraines. In accordance with the finding of non-radiative decay, a DSSC fabricated with SQM1a exhibited a significantly enhanced short-circuit current density, which revealed an efficient electron injection derived from the double-anchored and conformationally locked structure of SQM1a. Consequently, the performance of DSSCs fabricated with SQM1a was higher than the performance of those fabricated with SQM1b and MSQ. This indicates that substantial advantages can be derived by restricting the conformation of symmetrical squaraine dyes.

  一种具有对称结构的方形花菁染料，其在环丁烯核心的羰基上具有二氰乙烯基功能团（SQM1a），通过与具有一个羧基的不对称类似物（SQM1b）和标准方形花菁染料（MSQ）的比较，合成了该染料，以阐明由二氰乙烯基的立体排斥确保的构象锁定顺式形式对染料敏化太阳能电池（DSSCs）性能的影响。TiO2薄膜沉浸在染料溶液中的FT-IR光谱表明，染料与TiO2之间的键合是由对称地结合在染料π共轭体系上的两个羧基形成的。SQM1a的对称和构象锁定结构导致非辐射衰减速率的降低，这可能是由抑制方形花菁的可能光异构化引起的。与非辐射衰减的发现一致，采用SQM1a制备的DSSC表现出显著增强的短路电流密度，这揭示了源自SQM1a的双锚定和构象锁定结构的有效的电子注入。因此，采用SQM1a制备的DSSCs的性能高于采用SQM1b和MSQ制备的那些。这表明，通过限制对称方形花菁染料的构象，可以获得实质性的优势。
• Near-infrared Absorbing Squarylium Dyes with Linearly Extended π-Conjugated Structure for Dye-sensitized Solar Cell Applications
  作者：Takeshi Maeda、Yuuto Hamamura、Kyohei Miyanaga、Naoki Shima、Shigeyuki Yagi、Hiroyuki Nakazumi

  DOI：10.1021/ol2024345

  日期：2011.11.18

  A novel class of near-infrared absorbing squarylium sensitizers with linearly extended pi-conjugated structures, which were obtained by Pd-catalyzed cross-coupling reactions with stannylcyclobutenediones, has been developed for dye-sensitized solar cells. The cells based on these dyes exhibited a significant spectral response in the near-Infrared region over 750 nm in addition to the visible region.