5-(9,9,18,18,27,27-Hexahexyl-15,24-dithiophen-2-yl-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl)thiophene-2-carbaldehyde | 865347-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5-(9,9,18,18,27,27-Hexahexyl-15,24-dithiophen-2-yl-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl)thiophene-2-carbaldehyde
• CAS: 865347-71-3
• 化学式: C₇₆H₉₆OS₃
• 分子量: 1121.8
• InChiKey: UYDDPPHIKLJXQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  29.5
• 重原子数：
  80
• 可旋转键数：
  34
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(9,9,18,18,27,27-Hexahexyl-15,24-dithiophen-2-yl-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl)thiophene-2-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以94%的产率得到[5-(9,9,18,18,27,27-Hexahexyl-15,24-dithiophen-2-yl-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl)thiophen-2-yl]methanol
  参考文献：
  名称：

  梯度π共轭亚噻吩乙烯撑树枝状聚合物的固溶异质结光伏电池

  摘要：

  很好地合成了一系列基于5,5,10,10,15,15-六己基甲苯部分作为节点和不同长度的低聚亚乙烯基（OTV）单元作为支化臂的梯度π共轭树枝状大分子及其相应模型通过维蒂希-霍纳反应获得产量。所有新化合物的特征均是1 H和13C NMR光谱，元素分析和MALDI-TOF MS或ESI-MS。对它们的光物理性质的研究表明，梯度树突状支架不仅比其相应的模型化合物具有更高的摩尔吸收系数和更宽的吸收区域，而且相对于相应的OTV而言，还提高了PL量子产率。合适的HOMO和LUMO含量以及出色的成膜性能使这些分子成为有机太阳能电池的潜在候选者。使用这些树状聚合物作为供体，并用[6,6]-苯基-C 61丁酸甲酯作为受体，进行溶液处理的整体异质结太阳能电池的制备和测试。基于G0-4-2的设备的电源转换效率在空气质量1.5和100 mW cm -2的照度下，α为0.40％。这是迄今为止基于OTV的材料的最高记

  DOI：

  10.1002/asia.200900245
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 2,7,12-tri(2-thienyl)-5,5,10,10,15,15-hexa-n-hexyl-10,15-dihydro-5H-diindeno[1,2-a:1',2'-c]fluorene 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以46%的产率得到5-(9,9,18,18,27,27-Hexahexyl-15,24-dithiophen-2-yl-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  Nanosized Rigid π-Conjugated Molecular Heterojunctions with Multi[60]fullerenes:  Facile Synthesis and Photophysical Properties

  摘要：

  A series of large, rigid, new, well-defined, D-pi-B-A compounds with three chromophores(truxene moieties at the core, conjugated oligothiophenes as the branch bridges, and [60]pyrrolidinofullerene (C-60) segments as the end-capped groups) have been facilely developed in this contribution. Oligothiophene-functionalized truxene derivatives 1-29 are prepared by the Suzuki, the Sonogashira, and the Negishi cross-coupling reactions catalyzed by Pd(PPh3)(4) as well as the McMurry reaction, respectively. The 1,3-dipolar cycloaddition of the oligomers with C-60 and N-methylglycine yields a new family of star-shaped D-pi-B-A derivatives end-capped with pyrrolidinofullerene moieties as the active materials for photovoltaic devices in which one, two, three, or four C-60 moieties are allocated at the peripheral position of well-defined compounds, respectively. We also investigate the UV-vis and photoluminescence behaviors of these pyrrolidinofullerene-functionalized derivatives. The emission is obviously quenched after the inducement of the C-60 moieties. We also observe that the emission intensity is decreased with the increase in the number of C-60 moieties.

  DOI：

  10.1021/jo060097t

文献信息

• Novel highly fluorescent dendritic chiral amines: synthesis and optical properties
  作者：Hui Wang、Jin-Liang Wang、Si-Chun Yuan、Jian Pei、Wei-Wei Pei

  DOI：10.1016/j.tet.2005.06.068

  日期：2005.8

  An efficient approach to dendritic chiral amines through the allylation of optically active imines bearing chiral auxiliaries were developed. The addition of allylic zinc catalyzed by CeC13·7H2O to chiral imines derived from 2-thiophenecarboxaldehyde and α-amino acid esters conveniently and efficiently afforded the corresponding homoallylic amines with excellent diastereoselectivity. Such addition

  开发了一种通过带有手性助剂的旋光性亚胺的烯丙基化来制备树状手性胺的有效方法。CeC1 3 ·7H 2催化的烯丙基锌的添加衍生自2-噻吩甲醛和α-氨基酸酯的手性亚胺可​​以方便，有效地得到相应的具有非对映选择性的均烯丙基胺。使用多环芳族衍生物的二亚胺或三亚胺的这种加成反应也产生具有相似的非对映选择性的chhal多烯丙基树状胺。对它们的光物理性质（包括紫外可见吸收和荧光光谱以及圆二色性（CD））的研究表明，它不影响前体的吸收以诱导手性助剂。然而，整个分子表现出明显的CD行为。
• Nanosized Gradient π-Conjugated Thienylethynylene Dendrimers for Light Harvesting:  Synthesis and Properties
  作者：Jin-Liang Wang、Jia Luo、Liang-Hui Liu、Qi-Feng Zhou、Yuguo Ma、Jian Pei

  DOI：10.1021/ol0605427

  日期：2006.5.1

  [reaction: see text] A family of pi-conjugated dendrimers based on truxene and thienylethynylene units are synthesized via a mixed divergent/convergent growth approach. These dendrimers possess an intrinsic energy gradient from the periphery to the core through branches and thus show a broad absorption in the UV-vis range and an efficient energy transfer to the lower-energy center. The molecules hence

  [反应：见正文]通过混合的发散/会聚生长方法合成了基于二甲苯和噻吩基乙炔基单元的π-共轭树状聚合物。这些树枝状聚合物具有从外围到核心通过分支的内在能量梯度，因此在UV-vis范围内显示出广泛的吸收能力，并且可以有效地将能量转移至较低能量的中心。因此，分子具有用作光收集材料的潜力。
• Solution-Processed Bulk-Heterojunction Photovoltaic Cells Based on Dendritic and Star-Shaped D-π-A Organic Dyes
  作者：Jin-Liang Wang、Zhicai He、Hongbin Wu、Haibo Cui、Yan Li、Qihuang Gong、Yong Cao、Jian Pei

  DOI：10.1002/asia.200900686

  日期：2010.5.6

  A series of D‐π‐A organic dendritic and star‐shaped molecules based on three various chromophores (i.e., the truxene nodes, triphenylamine moieties as the donor, and benzothiadiazole chromophore as the acceptor) and their corresponding model compounds are facilely developed. Their photophysical and electrochemical properties are investigated in detail by UV/Vis absorption and photoluminescent spectroscopy

  方便地开发了基于三种不同发色团（即，戊二烯节点，三苯胺部分作为供体，苯并噻二唑发色团作为受体）的一系列D -π-A有机树枝状分子和星形分子及其相应的模型化合物。通过紫外/可见吸收和光致发光光谱以及循环伏安法详细研究了它们的光物理和电化学性质。通过改变树枝状序列的三个生色团之间的各种共轭间隔基（即单键，双键和三键），它们的光物理性质（即单光子吸收范围和双光子吸收截面值）被有效地调制。全部Dπ-A共轭低聚物在薄膜中显示出从250到700 nm的宽而强的吸收带。使用我们的低聚物作为施主，PCBM作为受主，对溶液处理的体异质结光伏器件进行了制造和测量。通过改变施主与受主的比例以及施主与受主之间的共轭间隔基，在较长波长范围内相对吸收强度的提高，基于我们的低聚物的设备的功率转换效率从DBTTr不断提高到TRTD2A。基于TRTD2A的器件的功率转换效率在AM 1.5和100 mW cm -2的光照下为0
• Star-Shaped Donor-π-Acceptor Conjugated Molecules: Synthesis, Properties, and Modification of Their Absorptions Features
  作者：Zheng-Ming Tang、Ting Lei、Jin-Liang Wang、Yuguo Ma、Jian Pei

  DOI：10.1021/jo100388c

  日期：2010.6.4

  star-shaped donor-π-acceptor meta-conjugated systems with broad absorption features were constructed through facilely synthetic routes, in which triphenylamine (TPA) moiety as an electron donor and 2-dicyanomethylen-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) unit as an electron acceptor were introduced in various ratios. The investigation of the photophysical properties indicated that the absorption bands

  通过简便的合成途径构建了具有宽吸收特征的轮廓分明的星形供体-π-受体间共轭体系，其中三苯胺（TPA）部分作为电子供体，而2-二氰基亚甲基-3-氰基-4,5，以各种比例引入作为电子受体的5-三甲基-2,5-二氢呋喃（TCF）单元。对光物理性质的研究表明，这些化合物的吸收带覆盖了从300至800 nm的整个可见光范围。例如，D1A2T2的吸收起始点位于薄膜中约780 nm处，并在606 nm处达到峰值。稳态和瞬态发射光谱表明，这些化合物在这种情况下具有分子内能量转移。元共轭系统，这在我们的计算研究中得到了进一步的支持。我们系统的结构变化为我们提供了对D-π-A系统中光学性能的调节策略的见识，并为我们提供了一系列宽吸收分子。
• Solution-Processed Bulk Heterojunction Photovoltaic Cells from Gradient π-Conjugated Thienylene Vinylene Dendrimers
  作者：Jin-Liang Wang、Chengmei Zhong、Zheng-Ming Tang、Hongbin Wu、Yuguo Ma、Yong Cao、Jian Pei

  DOI：10.1002/asia.200900245

  日期：2010.1.4

  Solution‐processed bulk heterojunction solar cells using these dendrimers as donor and [6,6]‐phenyl‐C61 butyric acid methyl ester as acceptor are prepared and tested. The power conversion efficiency of the devices based on G0-4-2 is 0.40 % under illumination of air mass 1.5 and 100 mW cm−2. This is the highest record value for OTV‐based materials to date. Although the absorption band of dendrimer G0-4-2 is

  很好地合成了一系列基于5,5,10,10,15,15-六己基甲苯部分作为节点和不同长度的低聚亚乙烯基（OTV）单元作为支化臂的梯度π共轭树枝状大分子及其相应模型通过维蒂希-霍纳反应获得产量。所有新化合物的特征均是1 H和13C NMR光谱，元素分析和MALDI-TOF MS或ESI-MS。对它们的光物理性质的研究表明，梯度树突状支架不仅比其相应的模型化合物具有更高的摩尔吸收系数和更宽的吸收区域，而且相对于相应的OTV而言，还提高了PL量子产率。合适的HOMO和LUMO含量以及出色的成膜性能使这些分子成为有机太阳能电池的潜在候选者。使用这些树状聚合物作为供体，并用[6,6]-苯基-C 61丁酸甲酯作为受体，进行溶液处理的整体异质结太阳能电池的制备和测试。基于G0-4-2的设备的电源转换效率在空气质量1.5和100 mW cm -2的照度下，α为0.40％。这是迄今为止基于OTV的材料的最高记