sym-heptaphenylcycloheptatriene | 1835-56-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: sym-heptaphenylcycloheptatriene
• 英文别名: heptaheptylcycloheptatriene；1,2,3,4,5,6,7-Heptaphenyl-cyclohepta-1,3,5-trien；Heptaphenylcycloheptatrien；Heptaphenyl-tropiliden；Heptaphenyltropyliden；1,2,3,4,5,6,7-Heptaphenylcyclohepta-1,3,5-triene；1,2,3,4,5,6,7-heptakis-phenylcyclohepta-1,3,5-triene
• CAS: 1835-56-9
• 化学式: C₄₉H₃₆
• 分子量: 624.825
• InChiKey: OJFAIVHEAYHXBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  49
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.02
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  sym-heptaphenylcycloheptatriene 在 lithium aluminium deuteride 、 溴 作用下， 生成 Heptaphenyldeuterio-tropiliden
  参考文献：
  名称：

  Heptaphenylcycloheptatrienyl Anion¹

  摘要：

  DOI：

  10.1021/ja01088a019
• 作为产物：
  描述：

  二氯甲基苯 在 sodium tetrahydroborate 、 potassium tert-butylate 作用下， 以 乙醇 、 对二甲苯 、 苯 为溶剂， 反应 39.0h， 生成 sym-heptaphenylcycloheptatriene
  参考文献：
  名称：

  串联高压晶体学-光学光谱揭示了压致变色荧光分子转子的非共价相互作用

  摘要：

  为了开发具有可预测和刺激响应发射的发光分子材料，有必要将其几何形状、堆积结构和非共价相互作用的变化与其光学性质的相关变化联系起来。在这里，我们证明高压单晶 X 射线衍射可以与高压紫外可见吸收和荧光发射光谱相结合，以阐明结构的细微变化如何影响光学输出。对称七苯基环庚三烯 ( Ph 7 C 7 H )是一种压致变色聚集诱导发射体，在高压下其吸收和发射光谱显示出红移。平行 X 射线测量可识别压力引起的特定苯基-苯基相互作用的变化，从而导致压致变色现象。相邻分子的苯环对接近稳定苯二聚体的几何形状，而构象变化改变了与松弛激发态相关的分子内苯基-苯基相互作用。这种串联晶体学和光谱分析提供了关于微妙的结构变化如何与Ph 7 C 7 H的光物理性质相关的见解，并且可以应用于类似化合物库，以提供具有类似转子几何形状的荧光有机分子的一般结构-性质关系。

  DOI：

  10.1021/jacs.3c05444

文献信息

• Extended Conjugation Attenuates the Quenching of Aggregation‐Induced Emitters by Photocyclization Pathways
  作者：Andrew T. Turley、Promeet K. Saha、Andrew Danos、Aisha N. Bismillah、Andrew P. Monkman、Dmitry S. Yufit、Basile F. E. Curchod、Marc K. Etherington、Paul R. McGonigal

  DOI：10.1002/anie.202202193

  日期：2022.6.13

  Reactions to shorten and lengthen the conjugation between oligoaryl alkene units of aggregation-induced emitters toggle between rapid photocyclization and efficient photoluminescence properties. Trienes are resistant to photocyclization, giving them higher photoluminescence quantum yields, whereas nonconjugated aryl alkene units cyclize readily to form extended polycyclic frameworks.

  缩短和延长聚集诱导发射体的低聚芳基烯烃单元之间的共轭的反应在快速光环化和高效光致发光特性之间切换。三烯能够抵抗光环化，从而具有更高的光致发光量子产率，而非共轭芳基烯烃单元很容易环化形成扩展的多环骨架。
• Excited-State Aromatic Interactions in the Aggregation-Induced Emission of Molecular Rotors
  作者：Jiri Sturala、Marc K. Etherington、Aisha N. Bismillah、Heather F. Higginbotham、William Trewby、Juan A. Aguilar、Elizabeth H. C. Bromley、Alyssa-Jennifer Avestro、Andrew P. Monkman、Paul R. McGonigal

  DOI：10.1021/jacs.7b08570

  日期：2017.12.13

  Small, apolar aromatic groups, such as phenyl rings, are commonly included in the structures of fluorophores to impart hindered intramolecular rotations, leading to.desirable solid-state luminescence properties. However, they are not normally considered to take part in through-space interactions that influence the fluorescent output. Here, we report on the photoluminescence properties of a series of phenyl-ring molecular rotors bearing three, five, six, and seven phenyl groups. The fluorescent emissions from two of the rotors are found to originate, not from the localized excited state as one might expect, but from unanticipated through-space aromatic-dimer states. We demonstrate that these relaxed dimer states can form as a result of intra- or intermolecular interactions across a range of environments in solution and solid samples, including conditions that promote aggregation-induced emission. Computational modeling also suggests that the formation of aromatic-dimer excited states may account for the photophysical properties of a previously reported luminogen. These results imply, therefore, that this is a general phenomenon that should be taken into account when designing and interpreting the fluorescent outputs of luminescent probes and optoelectronic devices based on fluorescent molecular rotors.
• SALTS OF THE HEPTAPHENYLTROPYLIUM ION AND THEIR STABILITY
  作者：Merle A. Battiste

  DOI：10.1021/ja01480a040

  日期：1961.10
• Synthesis, electronic spectra, and thermal behavior of bis(heptaphenylcycloheptatrienes)
  作者：James A. Harvey、Michael A. Ogliaruso

  DOI：10.1021/jo00883a008

  日期：1976.10
• Chromium and Molybdenum Carbonyl Complexes of C7Ph7H and C7Ph5Me2H and of C7Ph7H(CO), the Diels-Alder Adduct of Tetracyclone and Triphenylcyclopropene: Variable-Temperature NMR and X-ray Crystallographic Study
  作者：Lisa C. F. Chao、Hari K. Gupta、Donald W. Hughes、James F. Britten、Suzie Rigby、Alex D. Bain、Michael J. McGlinchey

  DOI：10.1021/om00003a015

  日期：1995.3

  The Diels-Alder reaction of tetraphenylcyclopentadienone (tetracyclone) with triphenylcyclopropene yields the adduct 2 with an endo hydrogen at C(7); thermal elimination of CO produces heptaphenylcycloheptatriene (la). This initially formed isomer with a pseudoequatorial phenyl substituent at the sp(3) position is sterically hindered and undergoes a conformational flip, forming Ib, which allows the phenyl group to occupy the favored pseudoaxial site. However, the remaining phenyls are sterically encumbered and slowed rotation of these rings can be monitored by H-1 and C-13 NMR spectroscopy. The intermediacy of conformer la is shown by the formation of isomers of C-7(p-tolyl)(2)Ph(5)H, arising via a series of [1,5] hydrogen shifts that are possible only for 1a and not for 1b. Similarly, use of 2,5-dimethyl-3,4-diphenylcyclopentadienone yields C(7)Me(2)Ph(5)H, 3, in which [1,5]-hydrogen shifts occur. 1 crystallizes in the triclinic space group P $($) over bar$$ 1 with a = 9.8320(10) Angstrom, b = 10.0260(10) Angstrom, c = 19.166(2) Angstrom, alpha = 92.194(1)degrees, beta = 90.57(1)degrees, gamma = 108.94(1)degrees, and V = 1785.2(3) Angstrom(3) for Z = 2. 2 crystallizes in the monoclinic space group P2(1)/n with a 12.829(4) Angstrom, b = 16.456(2) Angstrom, c = 18.226(3) Angstrom, beta = 110.06(1)degrees, and V = 3614.3(13) Angstrom(3) for Z = 4. The reaction of Cr(CO)(6) with C(7)Ph(7)H leads to incorporation of a Cr(CO)3 group on a peripheral phenyl ring rather than on the seven-membered ring. However, the tricyclic ketone 2, which is the precursor to 1, reacts with Mo(CO)(6) to give the pi-allyl complex (eta(5)-C(5)Ph(4)OH)Mo(CO)(2)(eta(3)C(3)Ph(3)H(2)) (10), in which the triphenylcyclopropene ring has been opened. 10 crystallizes in the triclinic space group P $($) over bar$$ 1 with a = 13.265(3) Angstrom, b = 13.561(3) Angstrom, c = 13.635(4) Angstrom, or 71.84(2)degrees, beta = 65.04(2)degrees, gamma = 61.20(1)degrees, and V = 1930.3(12) Angstrom(3) for Z = 2.