Dimethyl-4-(5''-methyl-5'-(5-methylthiophen-2-yl)-[2,2';4',2''-terthiophen]-5-yl)phthalate | 1449607-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: Dimethyl-4-(5''-methyl-5'-(5-methylthiophen-2-yl)-[2,2';4',2''-terthiophen]-5-yl)phthalate
• 英文别名: dimethyl 4-[5-[4,5-bis(5-methylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]benzene-1,2-dicarboxylate
• CAS: 1449607-29-7
• 化学式: C₂₈H₂₂O₄S₄
• 分子量: 550.744
• InChiKey: MONKJXXYJDWDSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Dimethyl-4-(5''-methyl-5'-(5-methylthiophen-2-yl)-[2,2';4',2''-terthiophen]-5-yl)phthalate 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以31%的产率得到6-(5''-Methyl-5'-(5-methylthiophen-2-yl)-[2,2':4',2''-terthiophen]-5-yl)-2,3-di-hydrophthalazine-1,4-dione
  参考文献：
  名称：

  Consequences of hydrogen bonding on molecular organization and charge transport in molecular organic photovoltaic materials

  摘要：

  报告描述了一项系统的分子结构-性质关系研究，旨在评估分子电子供体之间专用氢键相互作用对小分子异质结有机光伏器件的分子组装、吸收、电荷收集和性能的影响。研究人员合成了三个支链四噻吩供体发色团家族，它们在分子分散状态下具有几乎相同的电子和光学性质，但能够或不能通过氢键（H键）进行自缔合。邻苯二甲酰肼官能化的四噻吩具有H键“活性”，在溶液中（通过1H NMR）以及纯薄膜和混合薄膜（与C60）中（通过IR）表现出H键促进组装的特征。与H键“关闭”的对照化合物相比，H键衍生物显示出红移薄膜吸收（纯薄膜和与C60的混合薄膜）、不同颜色的块状固体以及更高的分解和熔化温度。由H键供体分子与C60作为电子受体的混合物制成的光伏器件显示出更长的电荷收集长度和外部量子效率，与非H键对照相比，功率转换效率提高了两倍以上，从0.49%提高到1.04%。我们预计这种方法可以推广到其他具有较低光学间隙的供体发色团，以捕获更长的波长光子，实现更高的功率转换效率。

  DOI：

  10.1039/c3ta13529b
• 作为产物：
  描述：

  4,4,5,5-Tetramethyl-2-(5''-methyl-5'-(5-methylthiophen-2-yl)-[2,2':4',2''-terthiophen]-5-yl)-1,3,2-dioxaborolane 、 4-溴邻苯二甲酸二甲酯 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 甲苯 为溶剂， 以61%的产率得到Dimethyl-4-(5''-methyl-5'-(5-methylthiophen-2-yl)-[2,2';4',2''-terthiophen]-5-yl)phthalate
  参考文献：
  名称：

  Consequences of hydrogen bonding on molecular organization and charge transport in molecular organic photovoltaic materials

  摘要：

  报告描述了一项系统的分子结构-性质关系研究，旨在评估分子电子供体之间专用氢键相互作用对小分子异质结有机光伏器件的分子组装、吸收、电荷收集和性能的影响。研究人员合成了三个支链四噻吩供体发色团家族，它们在分子分散状态下具有几乎相同的电子和光学性质，但能够或不能通过氢键（H键）进行自缔合。邻苯二甲酰肼官能化的四噻吩具有H键“活性”，在溶液中（通过1H NMR）以及纯薄膜和混合薄膜（与C60）中（通过IR）表现出H键促进组装的特征。与H键“关闭”的对照化合物相比，H键衍生物显示出红移薄膜吸收（纯薄膜和与C60的混合薄膜）、不同颜色的块状固体以及更高的分解和熔化温度。由H键供体分子与C60作为电子受体的混合物制成的光伏器件显示出更长的电荷收集长度和外部量子效率，与非H键对照相比，功率转换效率提高了两倍以上，从0.49%提高到1.04%。我们预计这种方法可以推广到其他具有较低光学间隙的供体发色团，以捕获更长的波长光子，实现更高的功率转换效率。

  DOI：

  10.1039/c3ta13529b

文献信息

• MODULAR SUPRAMOLECULAR ACTIVE LAYER AND ORGANIC PHOTOVOLTAIC DEVICES
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：US20140345682A1

  公开（公告）日：2014-11-27

  A photoactive layer for an organic photovoltaic device has a supramolecular assembly of donors or acceptors formed from a plurality of units that are mixed with electron acceptors or electron donors, respectively, to form an ordered or semi-ordered bulk heterojunction structure. Each unit is formed from a plurality of sub-units that are combined and ordered by hydrogen bonding or other non-covalent interactions to form units that by π-stacking and, optionally, other forces are organized into the supramolecular assembly. Each sub-unit includes at least one electron donor or acceptor moiety, at least one non-covalent interacting moiety, and a linking moiety between the non-covalent interacting moiety and the electron donor or electron acceptor moiety of the sub-unit. The organized supramolecular assembly connects donors or acceptors through the thickness of the photoactive layer, and allows parallel continuous electron acceptor or electron donor phases through the thickness of the active layer.

  一种有机光伏器件的光活性层具有供体或受体的超分子组装，由多个单元混合电子受体或电子供体形成有序或半有序的杂化结构。每个单元由多个亚单元组成，通过氢键或其他非共价相互作用组合和有序排列，形成通过π堆积和可选的其他力组织成超分子组装体。每个亚单元包括至少一个电子供体或受体基团，至少一个非共价相互作用基团，以及连接非共价相互作用基团和亚单元电子供体或电子受体基团之间的连接基团。有序的超分子组装体通过光活性层的厚度连接供体或受体，并允许平行连续的电子受体或电子供体相通过活性层的厚度。
• [EN] MODULAR SUPRAMOLECULAR ACTIVE LAYER AND ORGANIC PHOTOVOLTAIC DEVICES<br/>[FR] COUCHE ACTIVE SUPRAMOLÉCULAIRE MODULAIRE ET DISPOSITIFS PHOTOVOLTAÏQUES ORGANIQUES
  申请人：UNIV FLORIDA

  公开号：WO2013119783A1

  公开（公告）日：2013-08-15

  A photoactive layer for an organic photovoltaic device has a supramolecular assembly of donors or acceptors formed from a plurality of units that are mixed with electron acceptors or electron donors, respectively, to form an ordered or semi-ordered bulk heterojunction structure. Each unit is formed from a plurality of sub-units that are combined and ordered by hydrogen bonding or other non-covalent interactions to form units that by π-stacking and, optionally, other forces are organized into the supramolecular assembly. Each sub-unit includes at least one electron donor or acceptor moiety, at least one non-covalent interacting moiety, and a linking moiety between the non-covalent interacting moiety and the electron donor or electron acceptor moiety of the sub-unit. The organized supramolecular assembly connects donors or acceptors through the thickness of the photoactive layer, and allows parallel continuous electron acceptor or electron donor phases through the thickness of the active layer.
• Consequences of hydrogen bonding on molecular organization and charge transport in molecular organic photovoltaic materials
  作者：Benjamin M. Schulze、Nathan T. Shewmon、Jing Zhang、Davita L. Watkins、John P. Mudrick、Weiran Cao、Raghida Bou Zerdan、Anthony J. Quartararo、Ion Ghiviriga、Jiangeng Xue、Ronald K. Castellano

  DOI：10.1039/c3ta13529b

  日期：——

  Reported is a systematic molecular structure–property relationship study to evaluate the consequences of dedicated H-bonding interactions between molecular electron donors on molecular assembly, absorption, charge collection, and performance in small-molecule bulk heterojunction organic photovoltaic devices. Three families of branched quaterthiophene donor chromophores have been synthesized with members that share nearly identical electronic and optical properties in the molecularly dispersed state but are either capable or incapable of self-association by hydrogen bonding (H-bonding). Phthalhydrazide-functionalized quaterthiophenes are H-bond “active” and show signatures of H-bond promoted assembly in solution (by 1H NMR) and in both neat and blended (with C60) films (by IR). Compared to control compounds with H-bonding “turned off”, the H-bonded derivatives show red-shifted thin film absorption (neat and as blends with C60), different colors as bulk solids, and increased decomposition and melt temperatures. Photovoltaic devices made from blends of H-bonded donor molecules with C60 as the electron acceptor show improved charge collection length and external quantum efficiency resulting in a more than two-fold enhancement in power conversion efficiency relative to non-H-bonding controls, from 0.49% to 1.04%. We anticipate this approach could be generalized to include other donor chromophores with lower optical gap to harvest more longer-wavelength photons and achieve higher power conversion efficiencies.

  报告描述了一项系统的分子结构-性质关系研究，旨在评估分子电子供体之间专用氢键相互作用对小分子异质结有机光伏器件的分子组装、吸收、电荷收集和性能的影响。研究人员合成了三个支链四噻吩供体发色团家族，它们在分子分散状态下具有几乎相同的电子和光学性质，但能够或不能通过氢键（H键）进行自缔合。邻苯二甲酰肼官能化的四噻吩具有H键“活性”，在溶液中（通过1H NMR）以及纯薄膜和混合薄膜（与C60）中（通过IR）表现出H键促进组装的特征。与H键“关闭”的对照化合物相比，H键衍生物显示出红移薄膜吸收（纯薄膜和与C60的混合薄膜）、不同颜色的块状固体以及更高的分解和熔化温度。由H键供体分子与C60作为电子受体的混合物制成的光伏器件显示出更长的电荷收集长度和外部量子效率，与非H键对照相比，功率转换效率提高了两倍以上，从0.49%提高到1.04%。我们预计这种方法可以推广到其他具有较低光学间隙的供体发色团，以捕获更长的波长光子，实现更高的功率转换效率。