9,9-di(n-butyl)-2-(diphenylamino)-7-fluorenylboronic acid | 857144-40-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 9,9-di(n-butyl)-2-(diphenylamino)-7-fluorenylboronic acid
• 英文别名: 9,9-bis(n-butyl)-2-diphenylamino-7-fluorenylboronic acid；9,9-di-n-butyl-7-(diphenylamino)-2-fluorenylboronic acid；9,9-dibutyl-7-(diphenylamino)-2-fluorenylboronic acid；9,9-Bis(n-butyl)-2-diphenylamino-7-fluorenylboronic acid；[9,9-dibutyl-7-(N-phenylanilino)fluoren-2-yl]boronic acid
• CAS: 857144-40-2
• 化学式: C₃₃H₃₆BNO₂
• 分子量: 489.465
• InChiKey: QTIKUYXDNGFGED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.48
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,9-di(n-butyl)-2-(diphenylamino)-7-fluorenylboronic acid 、 2,5'''-dibromo-5,2';5',2'';5'',2'''-quaterthiophene 在 palladium diacetate potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 12.0h， 以67%的产率得到2,5'''-bis[2'-diphenylamino-9',9'-bis(n-butyl)-7'-fluorenyl]-5,2',5',2'',5'',2'''-quaterthiophene
  参考文献：
  名称：

  Ambipolar Diphenylamino End-Capped Oligofluorenylthiophenes as Excellent Electron-Transporting Emitters

  摘要：

  In addition to hole transport, diphenylamino-end-capped oligofluorenylthiophenes can exhibit efficient electron transport, in which the oligothiophene central core acts as an excellent electron-transporting moiety. The highly efficient undoped multilayer OLEDs using OF(2)TTP-NPh and OF(2)QTP-NPh as an electron-transporting emitter exhibited a maximum luminance of 19 800 and 11 800 cd m(-2) with a luminance efficiency up to 5.3 and 1.0 cd A(-1), respectively.

  DOI：

  10.1021/ol701561s
• 作为产物：
  描述：

  2-溴-9,9-二丁基芴 在 正丁基锂 、 硫酸 、 碘 、 铜 、 potassium carbonate 、 过碘酸 作用下， 以 四氢呋喃 、 三甘醇二甲醚 、 溶剂黄146 为溶剂， 反应 31.0h， 生成 9,9-di(n-butyl)-2-(diphenylamino)-7-fluorenylboronic acid
  参考文献：
  名称：

  具有增强的蓝光发射功能特性的二苯基氨基端基低聚芴：合成与结构-性质关系。

  摘要：

  已经开发了一系列新颖的单分散不对称和对称取代的二苯基氨基端基封端的芴，OF（2）-NPhR，R = H或An（An = 9-蒽）和OF（n）-NPh，n = 2-4，通过使用钯催化的铃木交叉偶联的收敛方法合成。已显示具有二苯氨基的低聚芴的封端在降低其第一电离电势，增强热稳定性和诱导良好的非晶态形态稳定性方面具有优势。通过调节二苯基氨基端基的数目和链长，已经确定了光学和发光性质的最佳共轭长度。在迄今为止报道的所有能够用作非掺杂蓝色发射体的寡芴中，OF（3）-NPh具有最佳的共轭长度，具有某些最佳的空穴传输和发蓝光性能。已经实现了7500 cd m（-2）的最大亮度和高达1.8 cd A（-1）的亮度效率。

  DOI：

  10.1002/chem.200401152

文献信息

• Low bandgap dicyanovinyl and tricyanovinyl oligothiophenes for solar cell applications
  申请人：Nano and Advanced Materials Institute Limited

  公开号：US08975419B2

  公开（公告）日：2015-03-10

  The invention relates to solution-processable, p-type, low-optical gap oligothiophene compounds for use in solar cell application, comprising at least one thiophene-containing group, at least one electron-withdrawing dicyanovinyl or tricyanovinyl group, and at least one electron-donating diphenylaminofluorenyl or N-alkylcarbazole group.

  这项发明涉及可溶解、p型、低光学能隙的寡噻吩化合物，用于太阳能电池应用，包括至少一个含噻吩基团、至少一个电子受体的二氰乙烯基团或三氰乙烯基团，以及至少一个电子给体的二苯胺基氟烯基团或N-烷基咔唑基团。
• Synthesis and photovoltaic properties of organic dyes containing N-fluoren-2-yl dithieno[3,2-b:2′,3′-d]pyrrole and different donors
  作者：Sunil Kumar、K.R. Justin Thomas、Chun-Ting Li、Kuo-Chuan Ho

  DOI：10.1016/j.orgel.2015.07.019

  日期：2015.11

  appended dithienopyrrole as electron rich linker, different arylamine/heterocyclic units as conjugating donors and cyanoacrylic acid as acceptor have been synthesized and characterized as sensitizers for dye-sensitized solar cells. The effect of different conjugated donors such as triarylamine, carbazole and phenothiazine on the photophysical, electrochemical and photovoltaic properties is investigated

  已经合成了新的有机染料，其含有芴附加的二噻吩并吡咯作为富电子连接体，不同的芳胺/杂环单元作为共轭施主，氰基丙烯酸作为受体，并被用作染料敏化太阳能电池的敏化剂。研究了不同的共轭供体，如三芳基胺，咔唑和吩噻嗪对光物理，电化学和光伏性质的影响。染料的光学和电化学性质受到共轭给体的强烈影响。包含吩噻嗪供体的染料表现出更长的波长吸收和低氧化电位。在染料模型上执行的随时间变化的密度泛函计算显示出电荷吸收特性，可以吸收更长的波长。J SC  = 14.01 mA cm -2）和高开路电压（V OC  = 738 mV）。
• Dye-sensitized solar cells based on organic dyes with naphtho[2,1-b:3,4-b′]dithiophene as the conjugated linker
  作者：Xiaoxu Wang、Lei Guo、Ping Fang Xia、Fan Zheng、Man Shing Wong、Zhengtao Zhu

  DOI：10.1039/c3ta12901b

  日期：——

  Naphtho[2,1-b:3,4-b′]dithiophene is used for the first time as the π-spacer for metal-free organic dyes in dye-sensitized solar cells (DSSCs). Four new donor–(π-spacer)–acceptor organic dyes using triarylamine or carbazole as the electron-donating group, cyanoacrylic acid as the electron-withdrawing anchoring moiety, and naphtho[2,1-b:3,4-b′]dithiophene as the linker were synthesized. The absorption, electrochemical, and photovoltaic properties of the dyes were investigated. DSSCs based on these dyes as sensitizers had efficiencies ranging from 3.98% to 4.60%. The highest efficiency was 4.60 ± 0.16% with a Jsc of 10.8 ± 0.4 mA cm−2, a Voc of 657 ± 5 mV, and a fill factor of 64.0 ± 0.2% under 100 mW AM 1.5 irradiation. The incident photon-to-current efficiency (IPCE) measurement showed that these dyes had high quantum efficiency over the visible range, and the long π-spacer of the molecule resulted in broader IPCE at long wavelength and high Jsc. Photovoltage transient was used to understand the electron recombination and the trends of the photovoltaic parameters (e.g. Voc and efficiency) of the DSSCs based on these organic dyes.

  首次采用萘并[2,1-b:3,4-b']二噻吩作为染料敏化太阳能电池（DSSCs）中不含金属有机染料的π-桥连单元。合成了四种新型供体-（π-桥连单元）-受体有机染料，分别使用三芳胺或咔唑作为电子供体基团，氰基丙烯酸作为电子吸引锚定部分，萘并[2,1-b:3,4-b']二噻吩作为连接单元。研究了这些染料的吸收、电化学和光伏特性。基于这些染料作为敏化剂的DSSCs效率范围从3.98%到4.60%。在100 mW AM 1.5辐照下，最高效率为4.60 ± 0.16%，对应的Jsc为10.8 ± 0.4 mA cm⁻²，Voc为657 ± 5 mV，填充因子为64.0 ± 0.2%。入射光子-电流效率（IPCE）测量显示，这些染料在可见光区域具有高量子效率，分子的长π-桥连单元导致在长波长处IPCE更宽，Jsc更高。使用光电压瞬态来理解基于这些有机染料的DSSCs的电子复合和光伏参数（如Voc和效率）的趋势。
• Synthesis and Structure - Property Relationships of Symmetric Ambipolar Quaterfluorene-Containing Oxadiazole as a Central Core and Diphenylamine as End-capping Moieties
  作者：Fan Yang、Xiao Ling Zhang、Mo Jun Xiong、Zi Jian Cao、Ping Fang Xia、Zhong Hui Li

  DOI：10.1071/ch07368

  日期：——

  A facile approach for the synthesis of the symmetric ambipolar quaterfluorene, OF(4)OX-NPh, with hole-transporting and electron-transporting moieties by Suzuki cross-coupling as a key reaction has been developed. This novel ambipolar quaterfluorene exhibits high thermal and electrochemical stabilities and is expected to possess potential application as a double charge-transfer and light-emitting material

  已经开发了一种通过铃木交叉偶联作为关键反应合成具有空穴传输和电子传输部分的对称双极四芴、OF(4)OX-NPh 的简便方法。这种新颖的双极性四芴具有很高的热稳定性和电化学稳定性，有望在单层有机发光二极管领域作为双电荷转移和发光材料具有潜在应用。
• Non-coplanar 9,9-diphenyl-substituted oligofluorenes with large two-photon absorption enhancement
  作者：Po Lam Wu、Ping Fang Xia、Zhong Hui Li、Xin Jiang Feng、Hoi Lam Tam、King Fai Li、Yong Jiao、Man Shing Wong、Kok Wai Cheah

  DOI：10.1039/b909909c

  日期：——

  The non-coplanar substituted phenyl rings at the 9-position of a fluorenyl unit can be involved in π-electron delocalization in which the resulting oligofluorenes exhibit a very large enhancement of two-photon absorption cross sections up to 2559 GM at 710 nm.

  芴基单元 9 位上的非共面取代苯基环可能参与了 π 电子析出，由此产生的低聚芴在 710 纳米波长下的双光子吸收截面有非常大的提高，最高可达 2559 GM。