3-环丁烯-1,2-酮,3-二苯基氨基-4-羟基- | 223582-26-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-环丁烯-1,2-酮,3-二苯基氨基-4-羟基-
• 中文别名: 3-环丁烯-1,2-酮,3-二苯基胺-4-醇
• 英文名称: 3-(diphenylamino)-4-hydroxy-cyclobut-3-ene-1,2-dione
• 英文别名: 3-Cyclobutene-1,2-dione, 3-(diphenylamino)-4-hydroxy-；3-hydroxy-4-(N-phenylanilino)cyclobut-3-ene-1,2-dione
• CAS: 223582-26-1
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: AXAFSDYGIMICGE-UHFFFAOYSA-N

物化性质

• 沸点：
  394.2±52.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,4-二甲基噻吩 、 3-环丁烯-1,2-酮,3-二苯基氨基-4-羟基- 以 甲苯 、 正丁醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  一种非对称方酸菁材料及其制备方法和应用

  摘要：

  本发明属于方酸菁材料制备技术领域，具体涉及一种非对称方酸菁材料及其制备方法和应用。本发明通过对C1和C2取代基的设计与选择，使得其光谱吸收峰位于蓝绿光吸收区域，用以制备有机蓝绿光敏感器件，满足蓝绿光传感、多通道光通信领域的应用需求；同时，本发明提供的非对称方酸菁材料溶液下的吸收半峰宽和薄膜形态下的吸收半峰宽均小于110nm，在制备光敏二极管方面有着十分重要的应用。此外，本发明提供的材料稳定性强，能够满足蒸镀、旋涂、喷墨打印等多种工艺。

  公开号：

  CN109053531B
• 作为产物：
  描述：

  3-diphenylamino-4-isopropoxycyclobut-3-ene-1,2-dione 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 以55%的产率得到3-环丁烯-1,2-酮,3-二苯基氨基-4-羟基-
  参考文献：
  名称：

  Squaraine dyes containing diphenylamine group: Effects of different type structures on material properties and organic photovoltaic performances

  摘要：

  Four donor-acceptor-donor (D-A-D') unsymmetrical squaraines (USQs) with different molecular skeletons (XZ-type and YZ-type), containing diphenylamine group with/without methoxy substituent were synthesized as donor materials in bulk-heterojunction (BHJ) organic photovoltaics (OPVs). The introduction of methoxy group in USQs has little different effects on the overall photovoltaic performance. Conversely, the different molecular skeleton types of the USQs have significant influence on their material properties and photovoltaic performances. Compared to BIDPSQ and BIDPOMeSQ with XZ-type molecular skeleton, IDPSQ and IDPOMeSQ with YZ-type molecular skeleton display closer solid-state packing, much lower highest occupied molecular orbital (HOMO) energy level, higher hole mobility and smaller phase separation domain size. Consequently, YZ-type USQs exhibit the most excellent performance with power conversion efficiency (PCE) of similar to 4%, which is approximately 300% higher than those of XZ-type USQs. Surprisingly, even though IDPSQ and IDPOMeSQ show wide band gaps, the corresponding devices still achieve a highest PCE of similar to 4%, which is comparable to or even higher than the PCEs of some reported SQ-based devices with low band gaps. These results indicate the YZ-type molecular skeleton and the electron-donating diphenylamine group are very promising to construct highly efficient squaraine donor materials.

  DOI：

  10.1016/j.dyepig.2019.107763

文献信息

• N,N-Di<i>aryl</i>anilinosquaraines and Their Application to Organic Photovoltaics
  作者：Siyi Wang、Lincoln Hall、Vyacheslav V. Diev、Ralf Haiges、Guodan Wei、Xin Xiao、Peter I. Djurovich、Stephen R. Forrest、Mark E. Thompson

  DOI：10.1021/cm2020803

  日期：2011.11.8

  spectra (λmax = 529–535 nm) relative to their symmetric counterparts. Compared to bis(N,N-diisobutylanilino)squaraine, both symmetrical and unsymmetrical N,N-diarylanilino squaraines show markedly broader absorption bands in solution than their N,N-dialkylanilino squaraine counterparts: the full width at half-maximum (fwhm) for N,N-diarylanilino squaraines range from 1280–1980 cm–1, while the fwhm value

  我们报告N，对称方酸菁染料的新衍生物N-二芳基具有高溶解度和高的吸收率（ε= 0.71-4.1×10苯胺取代基5中号-1 厘米-1在红色太阳光谱区域）（λ最大= 645-694 nm）使其成为有机光伏（OPV）应用的有希望的候选者。还制备了非对称的N，N-二异丁基苯胺基和N，N-二苯基苯胺基（二苯基氨基）方胺，相对于它们的对称对应物，它们给出了蓝移的吸收光谱（λmax = 529–535 nm）。与双（N，N-二异丁基苯胺基）方酸相比，对称和不对称的N，N-二芳基苯胺方酸在溶液中的吸收带比N，N-di烷基苯胺方酸的对应物要宽得多：N，N-二芳基苯胺方酸的半峰全宽（fwhm）为1280–1980 cm –1，而N，N-二异丁基苯胺基对苯二酚的fwhm值仅为630 cm –1。N，N-二芳基苯胺类方酸薄膜的吸收带进一步扩大到2500-3300 cm -1。N，N-Di芳基苯胺类方括号是荧光的，
• SQUARYLIUM COMPOUNDS AND INFRARED CUT FILMS, INFRARED CUT FILTERS AND ELECTRONIC DEVICES INCLUDING THE SAME
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20180282303A1

  公开（公告）日：2018-10-04

  A squarylium compound has high transmittance in a visible wavelength spectrum of light and is configured to selectively absorb light in an infrared/near infrared wavelength spectrum of light.

  一个方酰胺化合物在可见光波长范围内具有高透射率，并被配置为选择性地吸收红外/近红外波长范围内的光。
• Ionic Liquid Driven Nucleophilic Substitution of Squaric Acid to Squaramides
  作者：Peera Acharasatian、Siraporn Soonthonhut

  DOI：10.1055/a-1795-8322

  日期：2022.9

  crucial encumbrance for the synthesis of squaramides through nucleophilic substitution of squaric acid. The reactions must be performed in an aqueous medium since squaric acid is insoluble in virtually all organic solvents. The scope of amine nucleophiles was consequently restricted to those amines soluble in water. Owing to remarkable solvating ability of ionic liquid, reactions of squaric acid with

  溶解度是通过方酸的亲核取代合成方酰胺的关键障碍。反应必须在水性介质中进行，因为方酸几乎不溶于所有有机溶剂。因此，胺亲核试剂的范围仅限于那些溶于水的胺。由于离子液体的显着溶剂化能力，实现了方酸与多种结构多样的胺类亲核试剂的反应。有趣的是，在氯化 1-丁基-3-甲基咪唑鎓或 [bmim]Cl 中的无催化剂反应可以产生高达 99% 的产率的方酰胺。在同样的效果下，[bmim]Cl 可以重复使用至少三个循环。无催化剂、离子液体介导的方法扩大了反应物范围，并提供了一种简单、高效、
• Synthesis and Structures of Polymeric Mn, Co, Cu, and Zn Complexes of 3-Diphenylamino-4-hydroxycyclobut-3-ene-1,2-dione (Diphenylaminosquarate) and of the Salt [Ni(H₂O)₆][(C₆H₅)₂NC₄O₃]₂·2H₂O
  作者：Avril R. Williams、Bert D. Alleyne、Lincoln A. Hall、Andrew J. P. White、David J. Williams、Laurence K. Thompson

  DOI：10.1021/ic000390q

  日期：2000.11.13

  Reaction of M(NO3)2.xH2O (M = Mn, Co, Ni, Cu, Zn) with 3-diphenylamino-4-hydroxycyclobut-3-ene-1,2-dione (diphenylaminosquarate) produces the neutral polymeric species (M[mu-(C6H5)2NC4O3]2[H2O]2)n [M = Mn (1), Cu (2)]; (M[mu-(C6H5)2NC4O3][(C6H5)2NC4O3][H2O]3)n [M = Co (3), Zn (4)]; and in the case of Ni, the salt [Ni(H2O)6][(C6H5)2NC4O3]2.2H2O (5). Complexes 1 and 2 are isomorphous and crystallize

  M（NO3）2.xH2O（M = Mn，Co，Ni，Cu，Zn）与3-二苯基氨基-4-羟基环丁-3-烯-1,1,2-二酮（二苯基氨基方形）的反应生成中性聚合物（M [μ-（C6H5）2NC4O3] 2 [H2O] 2）n [M = Mn（1），Cu（2）]; （M [μ-（C6H5）2NC4O3] [（C6H5）2NC4O3] [H2O] 3）n [M = Co（3），Zn（4）]; 在镍的情况下，盐[Ni（H2O）6] [（C6H5）2NC4O3] 2.2H2O（5）。配合物1和2是同晶的，并且在单斜空间群P2（1）/ c中结晶，对于1，a = 13.138（1）A，b = 10.900（2）A，c = 9.269（2）A，beta = 96.07（1）度，Z =2。在空间组P2（1）/ c中，配合物3和4也是同晶的，其中a = 13.211（1）A，b = 11.038（1）A ，c =
• Squarylium compounds and infrared cut films, infrared cut filters and electronic devices including the same
  申请人：Samsung Electronics Co., Ltd.

  公开号：US11261172B2

  公开（公告）日：2022-03-01

  A squarylium compound has high transmittance in a visible wavelength spectrum of light and is configured to selectively absorb light in an infrared/near infrared wavelength spectrum of light.

  一种方酸菁化合物在可见光波长范围内具有高透射率，并且配置为选择性吸收红外/近红外光波长范围内的光线。