4-(对硝基苯乙烯基)苯乙炔 | 164467-32-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-(对硝基苯乙烯基)苯乙炔
• 英文名称: 4-( p-nitrostyryl)phenylacetylene
• 英文别名: (E)-4,4'-HC*CC6H4CH=CHC6H4NO2；(E)-HCCC6H4CH=CHC6H4NO2；HCC-4-C6H4-(E)-CH=CH-4-C6H4NO2；(E)-4,4'-HCCC6H4CH=CHC6H4NO2；(E)-4,4'-CCC6H4CHCHC6H4NO2；1-ethynyl-4-[(E)-2-(4-nitrophenyl)ethenyl]benzene
• CAS: 164467-32-7
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: DWOCSLWZHWQNBX-BQYQJAHWSA-N

物化性质

• 沸点：
  379.4±21.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(对硝基苯乙烯基)苯乙炔 、 cis-[RuCl₂(dppm)2] 在 NaPF₆ 、 Et₃N 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到trans-[Ru(C.tplbond.CC6H4CH=CHC6H4NO2-4,4',(E))Cl(dppm)2]
  参考文献：
  名称：

  Organometallic complexes for non-linear optics V

  摘要：

  A series of systematically-varied donor-acceptor octahedral ruthenium sigma-acetylide complexes of general formula trans-[Ru(C=CC(6)H(4)R-4)Cl(dppm)(2)] (R=H, NO2, C6H4NO2-4, CH=CHC6H4NO2-4,(E)) has been synthesized. An X-ray structural study of trans-[Ru(C=CC6H4C6H4NO2-4,4')Cl(dppm)(2)] reveals non-planarity of the biphenylene moiety in the solid state. Semi-empirical calculations employing ZINDO were performed on the acetylide complexes and the dichloro species cis- and trans-[RuCl2(dppm)(2)] to evaluate molecular quadratic optical non-linearities, beta; the results are consistent with (a) a significant increase in beta upon incorporation of a strong acceptor substituent, (b) a substantial increase in beta on chain lengthening, and (c) a 50% decrease in non-linearity upon rotation of phenylene-phenylene dihedral angle from coplanarity to orthogonality for the structurally-characterized complex.

  DOI：

  10.1016/s0022-328x(96)06197-9
• 作为产物：
  描述：

  在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-(对硝基苯乙烯基)苯乙炔
  参考文献：
  名称：

  Synthesis and Optical Properties, Including Two-Photon Absorption Cross-Sections, of Differentially Functionalized Starburst-Type π-Conjugated Molecules

  摘要：

  通过 Sonogashira 交叉偶联反应合成了不同对称性（D6h、D3h、D2h 和 C2v）的不同官能化六(对取代苯乙炔基)苯和六[4-(对取代苯乙烯基)苯乙炔基]苯衍生物。研究了这种星爆型 π 共轭体系的光学性质。其中，六[4-( 对二辛基氨基苯乙烯基)苯乙炔基]苯（5）在 800 纳米波长处显示出最大的双光子吸收截面δ = 818 GM，这是通过在甲苯溶液中使用 120 fs 激光脉冲进行开孔 Z 扫描测定的。

  DOI：

  10.1246/bcsj.82.1416

文献信息

• Synthesis and Nonlinear Optical Properties of η⁵-Monocyclopentadienyliron(II) Acetylide Derivatives. X-ray Crystal Structures of [Fe(η⁵-C₅H₅)(DPPE)(<i>p</i>-C⋮CC₆H₄NO₂)] and [Fe(η⁵-C₅H₅)(DPPE)((<i>E</i>)-<i>p</i>-C⋮CC₆H₄C(H)C(H)C₆H₄NO₂)]
  作者：M. Helena Garcia、M. Paula Robalo、Alberto R. Dias、M. Teresa Duarte、Wim Wenseleers、G. Aerts、Etienne Goovaerts、Marie P. Cifuentes、Steph Hurst、Mark G. Humphrey、Marek Samoc、Barry Luther-Davies

  DOI：10.1021/om0104619

  日期：2002.5.1

  increase in γ upon replacing Ru by the more easily oxidizable Fe and upon chain-lengthening the delocalizable π-bridging unit (proceeding from 4-C6H4 to (E)-4,4‘-C6H4CHCHC6H4). X-ray crystallographic structures of complexes [Fe(η5-C5H5)(DPPE)(p-C⋮CC6H4NO2)] and [Fe(η5-C5H5)(DPPE)((E)-p-C⋮CC6H4C(H)C(H)C6H4NO2)] were studied in order to investigate the existence of π-back-donation suggested by spectroscopic

  一系列所述类型的新的乙炔化物络合物的[Fe（η 5 -C 5 H ^ 5）（P⌒P）（p -C⋮CC 6 H ^ 4 R）]（P⌒P= DPPE（= 1,2-双（二苯基膦基）乙烷），（R）-PROPHOS（=（R）-（+）-1,2-双（二苯基膦基）丙烷），R = NO 2，C 6 H 4 NO 2，（Z）-C（ H）C（H）C 6 H 4 NO 2，（E）-C（H）C（H）C 6 H 4 NO 2）已经通过从所述前体卤化物抽象合成的[Fe（η 5 -C 5 H ^ 5）（P⌒P）（I）]和完全表征。络合物的二次超极化率（β）已通过1064 nm处的超瑞利散射测定。研究了从4-硝基苯基乙炔基到4-硝基联苯基乙炔基和4-硝基-（E）-苯乙烯基乙炔基对乙炔链长度的非线性响应的影响，揭示了有机金属分子材料中最高的首次超极化率的值。上非线性效率的比较绘制化合物的相关公知的家庭的[Ru（η 5 -C 5
• Organometallic complexes for nonlinear optics
  作者：Andrew M McDonagh、Marie P Cifuentes、Mark G Humphrey、Stephan Houbrechts、Joachim Maes、André Persoons、Marek Samoc、Barry Luther-Davies

  DOI：10.1016/s0022-328x(00)00420-4

  日期：2000.9

  and proceeding from 3d to 4d and 5d metal (2≤5≤7). Two-level-corrected nonlinearities reproduce the first two trends, but metal variation follows the sequence 2<7<5. The experimental and two-level-corrected nonlinearities for 6 (2795×10−30 and 406×10−30 esu, respectively), are amongst the largest observed thus far for organometallic complexes. Crystals of complexes 2 and 7 exhibit second-harmonic generation

  的氯配合物的制备反式- [的FeCl 2 （[R ，- [R）-diph} 2 ]（1）和炔基络合物反式- [M（4-CCC 6 ħ 4 R）氯（[R ，- [R）-diph} 2 ] [M = Fe，R = NO 2（2）; M = Ru，R = H（4），NO 2（5），（E）-CH ＝ CH-4-C 6 H 4 NO 2（6）；M = Os，R = NO 2（7）]，描述了掺入光学活性的二膦1，2-双（甲基苯基膦基）苯（diph）。通过循环伏安法测定的氧化电势随着2 < 7 < 5的增加而增加。分子二次非线性是由超瑞利散射在在引入受体基团（1064nm的增加4 < 5），桥连基团（的链伸长5 < 6从3d）中，并进行到4d和5d金属（2 ≤ 5 ≤ 7）。经两级校正的非线性再现了前两个趋势，但金属变化遵循以下顺序2 < 7 <5。为实验和两电平校正的非线性6（2795×10 -30和406×10
• Organometallic Complexes for Nonlinear Optics. 11.¹ Molecular Quadratic and Cubic Hyperpolarizabilities of Systematically Varied (Cyclopentadienyl)(triphenylphosphine)nickel σ-Arylacetylides
  作者：Ian R. Whittall、Marie P. Cifuentes、Mark G. Humphrey、Barry Luther-Davies、Marek Samoc、Stephan Houbrechts、André Persoons、Graham A. Heath、Denes Bogsányi

  DOI：10.1021/om961066z

  日期：1997.6.1

  complexes Ni(C⋮CR)(PPh3)(η-C5H5) (R = 4-C6H4NO2 (3), 4,4‘-C6H4C6H4NO2 (4), (E)-4,4‘-C6H4CHCHC6H4NO2 (5), (Z)-4,4‘-C6H4CHCHC6H4NO2 (6), 4,4‘-C6H4C⋮CC6H4NO2 (7), 4,4‘-C6H4NCHC6H4NO2 (8)) have been prepared. Electrochemical data for the series of complexes NiCl(PPh3)(η-C5H5) (1), Ni(C⋮CPh)(PPh3)(η-C5H5) (2), and 3−8 have been determined. Introduction of nitro substituent (in progressing from 2 to 3) results

  配合物的Ni（C⋮CR）（PPH 3）（η-C 5 H ^ 5）（R = 4-C 6 H ^ 4 NO 2（3），4,4'--C 6 H ^ 4 Ç 6 ħ 4 NO 2（4），（ê）-4,4'--C 6 H ^ 4 CH CHC 6 H ^ 4 NO 2（5），（ž）-4,4'--C 6 H ^ 4 CH CHC 6 H ^ 4 NO 2（在图6）中，已经制备了4,4'-C 6 H 4 C⋮CC 6 H 4 NO 2（7），4,4'-C 6 H 4 N CHC 6 H 4 NO 2（8）。为系列复合物的电化学数据的NiCl（PPH 3）（η-C 5 H ^ 5）（1），镍（C⋮CPH）（PPH 3）（η-C 5 H ^ 5）（2），和3 - 8已经确定。硝基取代基的引入（在进展从2到3）导致在镍大幅增加II / III的氧化电位，所有这些都对从一环进展丢失（3），以两环（4 - 8）发色
• EMISSIVE AND BROADBAND NONLINEAR ABSORBING METAL COMPLEXES AND LIGANDS AS OLED, OPTICAL SWITCHING OR OPTICAL SENSING MATERIALS
  申请人：Sun Wenfang

  公开号：US20120100628A1

  公开（公告）日：2012-04-26

  Platinum (II) terdentate or bidentate complexes with non-linear optical properties are provided. The complexes have a broadband spectral and temporal response, and strong reverse saturable absorption and two-photon absorption in the visible and the near-IR region. As such, the complexes are useful for organic light-emitting diodes and optical-switching or sensing devices.

  提供具有非线性光学性质的铂(II)三齿或二齿配合物。这些配合物具有宽带谱和时间响应，以及在可见光和近红外区域具有强反饱和吸收和双光子吸收。因此，这些配合物可用于有机发光二极管和光开关或传感器装置。
• Organometallic complexes for non-linear optics XII syntheses and second-order susceptibilities of (neomenthyldiphenylphosphine) gold σ-arylacetylides: X-ray crystal structures of Au(C≡CPh) (nmdpp) and Au((E)-4,4′-C≡CC6H4CH=CHC6H4NO2)(nmdpp)
  作者：Ian R. Whittall、Mark G. Humphrey、Marek Samoc、Barry Luther-Davies、David C.R. Hockless

  DOI：10.1016/s0022-328x(97)00196-4

  日期：1997.10

  The series of complexes Au(C=CR)(nmdpp) (R = Ph (2), 4-C6H4NO2 (3), 4,4'-C6H4C6H4NO2 (4), (E)-4,4'-C6H4CH=CHC6H4NO2 (5), (Z)-4,4'-C6H4CH=CHC6H4NO2 (6), 4,4'-C6H4C=CC6H4NO2 (7), 4,4'-C6H4N=CHC6H4NO2 (8); nmdpp = (+)-neomenthyldiphenylphosphine) has been synthesized by reaction of AuCl(nmdpp) with the corresponding acetylene and methoxide in the presence of trace amounts of a phosphine oxide, and complexes 2 and 5 have been structurally characterized. Complexes 2-8 and analogous (triphenylphosphine)gold acetylides and precursor (phosphine)gold chlorides have been examined for their second-order bulk susceptibilities chi((2)) by the Kurtz powder technique, with the largest response (ca. 2 x urea) being that from 3. (C) 1997 Elsevier Science S.A.