2,6-diphenyl-(4H-pyran-4ylidene)-diphenylphosphine oxide | 129806-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-diphenyl-(4H-pyran-4ylidene)-diphenylphosphine oxide
• 英文别名: 2,6-diphenyl(4H-pyran-4-ylidene)diphenylphosphine oxide；(2,6-diphenyl-4H-pyran-4-yl)diphenylphosphine oxide；2,6-diphenyl-(4H-pyran-4-yl)diphenylphosphine oxide；4-diphenylphosphoryl-2,6-diphenyl-4H-pyran
• CAS: 129806-51-5
• 化学式: C₂₉H₂₃O₂P
• 分子量: 434.474
• InChiKey: LZPVGBOZNDKSFX-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  619.0±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-diphenyl-(4H-pyran-4ylidene)-diphenylphosphine oxide 在 lead dioxide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Abaev, V. T.; Karsanov, I. V.; Urtaeva, Zh. Kh., Journal of general chemistry of the USSR, 1990, vol. 60, # 5, p. 891 - 898

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯基甲氧基膦 、 2,6-Diphenylpyrylium tetrafluoroborate 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以94%的产率得到2,6-diphenyl-(4H-pyran-4ylidene)-diphenylphosphine oxide
  参考文献：
  名称：

  Synthesis, Characterization, and Optical Properties of 4H-Pyran-4-ylidene Donor-Based Chromophores: The Relevance of the Location of a Thiophene Ring in the Spacer

  摘要：

  A series of new 4H-pyran-4-ylidene donor-based chromophores with a thiophene ring in the spacer has been synthesized. The linear and nonlinear optical (NLO) properties of these compounds have been determined and compared with the results of computational calculations. The position of the thiophene ring proved essential to optimize the figure of merit mu beta, with the best results obtained when the heterocyclic system was closer to the donor moiety.

  DOI：

  10.1021/jo300373m

文献信息

• Dithienopyrrole as a Rigid Alternative to the Bithiophene π Relay in Chromophores with Second-Order Nonlinear Optical Properties
  作者：A. Belén Marco、Natalia Martínez de Baroja、Santiago Franco、Javier Garín、Jesús Orduna、Belén Villacampa、Alejandro Revuelto、Raquel Andreu

  DOI：10.1002/asia.201402870

  日期：2015.1

  4H‐Pyranylidene‐containing push‐pull chromophores built around a bithiophene (BT) π relay or a rigidified thiophene‐based unit, namely cyclopenta[1,2‐b:3,4‐b′]dithiophene (CPDT) or dithieno[3,2‐b:2′,3′‐d]pyrrole (DTP), have been synthesized and characterized. The effect of these different relays on the polarization and the second‐order nonlinear optical (NLO) properties has been studied. For the sake of

  4 ħ -Pyranylidene含围绕双噻吩（BT）π继电器或僵化基于噻吩的单元，即环戊二烯并内置推挽生色团[1,2 b：3,4- b ']二噻吩（CPDT）或二噻吩并[已合成并表征了3,2‐ b：2'，3'‐ d ]吡咯（DTP）。研究了这些不同继电器对偏振和二阶非线性光学（NLO）特性的影响。为了比较，报告了相应的dithieno [3,2‐ b：2′，3′‐ d噻吩（DTT）衍生物也已包括在讨论中。用加固单元（CPDT，DTP）替换BT核心会导致极化更多的系统。计算得出的NBO电荷和电化学测量结果表明，二噻吩并吡咯具有显着的施主特性，可以在施主和受主之间进行重要的电荷转移。BT中继的刚性对NLO响应的影响取决于受体强度。对于所使用的最薄弱的受体（硫代巴比妥酸），从BT中继到僵化单元传递总是涉及在增加μβ 0品质因数。然而，对于最强受体（2-二氰基亚甲基-3-氰基-1,4,5,5-三甲基-2
• Pyranylidene/trifluoromethylbenzoic acid-based chromophores for dye-sensitized solar cells
  作者：Raquel Royo、Amelia Domínguez-Celorrio、Santiago Franco、Raquel Andreu、Jesús Orduna

  DOI：10.1016/j.dyepig.2022.110566

  日期：2022.10

  enhancement of the molar extinction coefficient, being slightly when a hexyl chain is introduced in the thiophene ring, but does not modify the oxidation potential. For the preparation of derived solar cells an antiaggregant is essential in all cases. The photovoltaic performance is sensitive to the structural modification of the dye: the CF3 group and the hexyl chain of the thiophene spacer were shown

  报道了基于 4 H-亚吡喃基部分作为供体部分的五种染料的合成和光伏研究。带有/不带有乙炔基键的噻吩单元充当π-中继，苯甲酸充当带有/不带有三氟甲基的锚定基团。通过使用联合实验和理论方法分析它们的电化学和光学性质。三氟甲基基团的存在导致摩尔消光系数的提高，当在噻吩环中引入己基链时会略微提高，但不会改变氧化电位。 对于衍生太阳能电池的制备，抗聚集剂在所有情况下都是必不可少的。光伏性能对染料的结构改性很敏感：CF 3基团和噻吩间隔基的己基链显示可以提高效率。π-间隔区中缺乏三键会降低光伏效率，三氟甲基会导致染料负载量降低，但复合过程会减少。这些结果与进行的电化学阻抗谱研究一致。此外，有机染料还用荧光灯（室内条件）进行了测试，导致效率提高，最佳染料达到 36%。
• Organic sensitizers bearing a trialkylsilyl ether group for liquid dye sensitized solar cells
  作者：Raquel Pérez-Tejada、Natalia Martínez de Baroja、Santiago Franco、Laia Pellejà、Jesús Orduna、Raquel Andreu、Javier Garín

  DOI：10.1016/j.dyepig.2015.07.026

  日期：2015.12

  In this work we present the synthesis, optical characterization and performance of five metal-free sensitizers for dye-sensitized solar cells (DSSC). All dyes include, for the first time, a trialkylsilyl ether group in the pi-conjugated bridge (a thiophene ring). The influence of different donor unities, like triarylamine (TPA), 4H-pyranylidene and dithiafulvene has been evaluated in DSSC with a liquid I-3/I- electrolyte, obtaining the best results with the 4H-pyranylidene moiety. The size and the position of the bulky group have a great importance in the efficiency of the final devices.In order to explain the recombination processes and electron life-time, charge extraction (CE) and transient photovoltage (TPV) experiments have been carried out. (C) 2015 Elsevier Ltd. All rights reserved.
• Influence of thiazole regioisomerism on second-order nonlinear optical chromophores
  作者：Elena Galán、Raquel Andreu、Javier Garín、Laura Mosteo、Jesús Orduna、Belén Villacampa、Beatriz E. Diosdado

  DOI：10.1016/j.tet.2012.05.123

  日期：2012.8

  Two series of matched and mismatched donor-thiazole-acceptor chromophores have been synthesized to disclose the role that the orientation of the thiazole ring plays on their second-order nonlinear optical (NLO) properties. Whereas previous theoretical studies predict that the matched systems show markedly higher NLO responses, our experimental results do not parallel this trend, showing differences between regioisomers much lower than those predicted. (C) 2012 Elsevier Ltd. All rights reserved.
• Efficient second-order nonlinear optical chromophores based on dithienothiophene and thienothiophene bridges
  作者：A. Belén Marco、Raquel Andreu、Santiago Franco、Javier Garín、Jesús Orduna、Belén Villacampa、Raquel Alicante

  DOI：10.1016/j.tet.2013.03.027

  日期：2013.5

  Two series of push-pull systems bearing dithienothiophene or thienothiophene as (part of) pi-conjugated spacer have been synthesized. These compounds combine high second-order molecular non-linearities with good thermal stabilities, showing one of the thienothiophene (TT) derivative the highest mu beta(0) value found for a 4H-pyranylidene-containing merocyanine. (C) 2013 Elsevier Ltd. All rights reserved.