1,3-diphenylnaphtho[2,3-c]furan | 18929-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1,3-diphenylnaphtho[2,3-c]furan
• 英文别名: 1,3-Diphenyl-naphtho<2,3-c>furan；1,3-diphenylbenzo[f][2]benzofuran
• CAS: 18929-57-2
• 化学式: C₂₄H₁₆O
• 分子量: 320.39
• InChiKey: ABHLELFSMPEUTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-diphenylnaphtho[2,3-c]furan 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 2,3-dicyano-1,4-diphenylanthracene
  参考文献：
  名称：

  Mono-Aromatic Ring-Fused versus Adjacently Di-Aromatic Ring-Fused Tetraazaporphyrins:  Regioselective Synthesis and Their Spectroscopic and Electrochemical Properties

  摘要：

  A method which preferentially produces adjacently di-aromatic ring-substituted tetraazaporphyrins (TAPS) has been developed, and their electrochemical and spectroscopic properties have been studied and compared with those of the corresponding series of mono-aromatic ring-fused TAPS. Mono-aromatic ring-fused TAPS show a split Q-band, and the splitting energy increases with increasing size of the aromatic ring. In addition, for the split Q-bands, the relative intensity of the band at longer wavelength decreases with increasing molecular size of the fused aromatics, compared with the shorter wavelength band. In the di-aromatic ring-fused TAPS, this kind of splitting is not seen, and only a shift of the band is observed. The intensity and band position of the split or unsplit Q-bands are quantitatively evaluated by simultaneous band deconvolution analysis, using both electronic absorption and magnetic circular dichroism spectra. The preparation of these TAP compounds has made it possible to adjust the Q-band position in a stepwise manner between ca. 600 and 750 rim. The first reduction and oxidation potentials of the TAP ring shift negatively with increasing number and size of the fused aromatics. The extent of the shift is found to be very small for the LUMOs but significant for the HOMOs. These spectroscopic and electrochemical properties are almost perfectly reproduced by molecular orbital calculations within the framework of the Pariser-Parr-Pople approximation. In particular, a small variation of the LUMO level and large destabilization of the HOMO level on ring expansion are rationalized from the extent of stretch of molecular orbitals: i.e., since the LUMOs are localized in the central TAP moiety irrespective of the molecular size, while the HOMOs have appreciable coefficients even over the fused aromatics, the HOMO level destabilizes while the LUMO level remains constant with increasing molecular size. In one CoTAP derivative, Co-III/II and the first ligand oxidation couples occur experimentally at the same potential.

  DOI：

  10.1021/ja012382u
• 作为产物：
  描述：

  1,3-dihydro-1,3-diphenylnaphtho[2,3-c]-furan-1-ol 在 溶剂黄146 作用下， 以72%的产率得到1,3-diphenylnaphtho[2,3-c]furan
  参考文献：
  名称：

  Synthesis and Photophysical Properties of Dihydroheptacenes:  New Blue-Emitting Materials

  摘要：

  7,16-Dihydroheptacenes (1-3) substituted at the 6, 8, 15, and 17 positions are synthesized as blue emitters potentially useful in organic light emitting diodes (OLEDs). The photophysical properties of 1 - 3 ( lambda(max) = 424- 428 nm, Phi(F) = 0.15- 0.21, tau(F) = 2.35 - 2.67 ns in CH2Cl2) are discussed. They are shown to be stable and efficient blue emitters in the solid state (Phi(F) = 0.37 - 0.44). The X-ray crystal structure of 1 is reported.

  DOI：

  10.1021/jo0601314

文献信息

• Synthesis and Optical Properties of Phenylene-Containing Oligoacenes
  作者：Rebecca R. Parkhurst、Timothy M. Swager

  DOI：10.1021/ja3043883

  日期：2012.9.19

  Synthesis of a new class of fully unsaturated ladder structures, phenylene-containing oligoacenes (POAs), using 3,4-bis(methylene)cyclobutene as a building block for sequential Diels-Alder reactions is described. The geometric effects of strain and energetic cost of antiaromaticity can be observed via the optical and electrochemical properties of the reported compounds. The resulting shape-persistant

  描述了使用 3,4-双 (亚甲基) 环丁烯作为连续 Diels-Alder 反应的构建单元合成一类新的完全不饱和梯形结构，即含亚苯基的低聚并苯 (POA)。通过所报道化合物的光学和电化学性质，可以观察到抗芳香性的应变和能量成本的几何效应。由此产生的形状持久梯形结构包含相邻的发色团，这些发色团彼此部分电子隔离，同时仍会降低材料的带隙。
• Solid‐State Generation of Diarylisonaphthofuran and Its Mechanochemical Diels–Alder Reaction with Epoxynaphthalene
  作者：Yoshifumi Wada、Keidai Tsuchihashi、Masayoshi Kanzaki、Toshiyuki Hamura

  DOI：10.1002/chem.202302660

  日期：2023.12.11

  A solid-state generation method for diarylisonaphthofurans using 1,3-diaryl-1,3-dihydronaphthofuranols has been developed. The generated reactive molecules were stable in the solid state and could be stocked without any precaution. X-ray analysis revealed a typical quinoidal structure. Furthermore, mechanochemical Diels-Alder reaction of 1,3-diarylisonaphthofurans with epoxynaphthalene gave synthetically

  开发了一种使用 1,3-二芳基-1,3-二氢萘呋喃醇固态生成二芳基异萘呋喃的方法。产生的反应分子在固态下是稳定的，可以在没有任何预防措施的情况下储存。 X射线分析显示出典型的醌型结构。此外，1,3-二芳基异萘呋喃与环氧萘的机械化学狄尔斯-阿尔德反应产生了合成上有吸引力的二环氧并五苯。
• Use of phenyl vinyl sulfoxide as an acetylene equivalent in Diels-Alder cycloadditions
  作者：Leo A. Paquette、Rudi E. Moerck、Bijan Harirchian、Philip D. Magnus

  DOI：10.1021/ja00473a044

  日期：1978.3
• Probing the spatial requirements for [60]fullerene–[60]fullerene π-stacking and the syn addition of [60]fullerenes across acenes
  作者：Glen P. Miller、Jonathan Briggs

  DOI：10.1016/j.tetlet.2003.11.010

  日期：2004.1

  The reaction between 2 equiv of [60]fullerene and 6,8,15,17-tetraphenylheptacene-7,16-quinone leads to both cis and trans-bis[60]fullerene adducts. This result contrasts sharply with the highly diastereoselective syn additions of [60]fullerenes across 6,13-diphenylpentacene and 6,8,15,17-tetraphenylheptacene. The importance of spatially dependent [60]fullerene-[60]fullerene pi-stacking interactions in promoting a syn addition of [60]fullerenes is discussed. (C) 2003 Elsevier Ltd. All rights reserved.
• Condensed cyclobutane aromatic compounds. XXX. Synthesis of some unusual 2,3-naphthoquinonoid heterocycles. A synthetic route to derivatives of naphtho[2,3-b]biphenylene and anthra[b]cyclobutene
  作者：Michael P. Cava、J. P. VanMeter

  DOI：10.1021/jo01255a012

  日期：1969.3