9,9-di(n-butyl)-7-(trimethylsilyl)-2-fluorenylboronic acid | 911304-21-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9,9-di(n-butyl)-7-(trimethylsilyl)-2-fluorenylboronic acid
• 英文别名: (9,9-Dibutyl-7-trimethylsilylfluoren-2-yl)boronic acid；(9,9-dibutyl-7-trimethylsilylfluoren-2-yl)boronic acid
• CAS: 911304-21-7
• 化学式: C₂₄H₃₅BO₂Si
• 分子量: 394.437
• InChiKey: WJTGEFUCUXWGGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,9-di(n-butyl)-7-(trimethylsilyl)-2-fluorenylboronic acid 在 palladium diacetate 碘 、 silver trifluoroacetate 、 potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 生成 1-phenyl-2-(4-tert-butylphenyl)-5-{3-[9',9'-di-n-butyl-7'-iodo-2'-fluorenyl]phenyl}-1,3,4-triazole
  参考文献：
  名称：

  Synthesis and Light-Emitting Properties of Bipolar Oligofluorenes Containing Triarylamine and 1,2,4-Triazole Moieties

  摘要：

  A facile approach for synthesis of bipolar oligofluorenes, TAZ-OF(n)-NPh, n) 2 or 3 end-capped with hole-transporting diphenylamino and electron-transporting triazole moieties by Suzuki cross-coupling as the key reaction has been developed. This novel bipolar oligofluorenes exhibited blue-emission, high thermal and morphological stabilities. The single-layer OLED based on TAZ-OF(2)-NPh exhibited superior device performance with a maximum luminance of 1128 cd m(-2) and luminance efficiency of up to 0.83 cd A(-1).

  DOI：

  10.1021/ol0615477
• 作为产物：
  描述：

  2,7-dibromo-9,9-dibutyl-9H-fluorene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 9,9-di(n-butyl)-7-(trimethylsilyl)-2-fluorenylboronic acid
  参考文献：
  名称：

  Synthesis and Light-Emitting Properties of Bipolar Oligofluorenes Containing Triarylamine and 1,2,4-Triazole Moieties

  摘要：

  A facile approach for synthesis of bipolar oligofluorenes, TAZ-OF(n)-NPh, n) 2 or 3 end-capped with hole-transporting diphenylamino and electron-transporting triazole moieties by Suzuki cross-coupling as the key reaction has been developed. This novel bipolar oligofluorenes exhibited blue-emission, high thermal and morphological stabilities. The single-layer OLED based on TAZ-OF(2)-NPh exhibited superior device performance with a maximum luminance of 1128 cd m(-2) and luminance efficiency of up to 0.83 cd A(-1).

  DOI：

  10.1021/ol0615477

文献信息

• End-Capped Terfluorene Derivatives: Synthesis and Structure - Functional Property Relationships
  作者：Mo Jun Xiong、Zhong Hui Li、Man Shing Wong

  DOI：10.1071/ch07025

  日期：——

  linear and non-linear optical properties, and fluorescence and electrochemical properties of the terfluorene derivatives are also investigated and discussed. The preliminary results show that end-capping of the terfluorene with diphenylamino groups, especially with dendrons, has been shown to offer advantages in terms of lowering the first ionization potential, enhancing thermal stability, and inducing

  基于三芳基胺和咔唑部分，OF(3)R´–R，R´ = Bu 或 Ph，R = H，NPh 或 EG，已通过以下方法合成了一系列单分散对称三芴使用钯催化的 Suzuki 交叉偶联或铜催化的 Buchwald 胺化作为关键反应的收敛方法。还研究和讨论了特芴衍生物的功能特性，包括热稳定性、线性和非线性光学特性以及荧光和电化学特性。初步结果表明，用二苯氨基，尤其是用树枝对四芴进行封端，在降低第一电离电位、提高热稳定性、
• 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。
• Highly Efficient Multiphoton-Absorbing Quadrupolar Oligomers for Frequency Upconversion
  作者：Xin Jiang Feng、Po Lam Wu、King Fai Li、Man Shing Wong、Kok Wai Cheah

  DOI：10.1002/chem.201002227

  日期：2011.2.18

  of quadrupolar oligomers PhN‐OF(n)‐NPh and PhN‐OF(n)‐TAZ‐OF(n)‐NPh, only the former exhibit remarkably intense and highly efficient multiphoton‐excited frequency‐upconverted deep blue lasing, which gives rise to record high lasing efficiency of 0.097 % and very narrow of full width at half‐maximum of the lasing spectra. Our findings suggest that quadrupolar‐type molecules/oligomers are superior for

  两个串联四极二苯基氨基封端的寡聚芴的，PHN-OF（Ñ）-NPh（Ñ = 2-5）和PHN-OF（Ñ）-TAZ-OF（Ñ）-NPh（Ñ= 1–4）具有一个吸电子的1,2,4-三唑（TAZ）部分作为中心核，并带有D–π–A–π–D结构基序（D =施主，A =受体），通过钯催化的9,9-二丁基-7-（二苯氨基）-2-芴基硼酸和相应的（1,2,4-三唑基）芳基卤化物的Suzuki交叉偶联合成。在用红外飞秒激光泵浦时，这些低聚物显示出非常强的多光子激发蓝色光致发光。相较于相应的d-π-A对应具有最高三光子吸收横截面的这些d-π-d和d-π-A-π-d的四极寡聚芴表现出优良的三光子吸收特性（σ 3）的高达2.72×10 −77  cm 6  s 2。尽管两种类型的四极低聚物PhN-OF（n）-NPh和PhN-OF（n）-TAZ-OF（n）-NPh具有相当的线性和多光子吸收特性，但只有前者表现出非常强
• Fluorene-Based π-Conjugated Oligomers for Efficient Three-Photon Excited Photoluminescence and Lasing
  作者：Xin Jiang Feng、Po Lam Wu、Hoi Lam Tam、King Fai Li、Man Shing Wong、Kok Wai Cheah

  DOI：10.1002/chem.200901460

  日期：2009.11.2

  π‐conjugated oligomers that includes extended oligofluorenes and oligothienylfluorenes has been synthesized by means of the palladium‐catalyzed Suzuki cross‐coupling of 9,9‐dibutyl‐7‐(diphenylamino)‐2‐fluorenylboronic acid and the corresponding 1,2,4,‐triazole‐based aryl halide as a key step. It was demonstrated that efficient two‐ and three‐photon excited photoluminescence and lasing in the blue region

  通过钯催化的Suzuki交联偶联反应9，合成了一系列新颖的二苯基氨基和1,2,4-三唑封端的芴基π共轭低聚物，包括扩展的低聚芴和低聚噻吩基芴。 9-二丁基-7-（二苯氨基）-2-芴基硼酸和相应的基于1,2,4，三唑的芳基卤化物是关键步骤。结果表明，通过在这些材料上泵浦近红外飞秒激光，可以在蓝色区域获得有效的两光子和三光子激发的光致发光和激光发射。尽管高荧光和延伸的低聚芴的吸收和发射最大值达到饱和极限，但在同源低聚系列中，对于最佳的三光子吸收横截面，仍存在有效的共轭长度。另一方面，在飞秒范围内已获得−77  cm 6  s 2，从而突显了该系列光子材料的潜力。无腔三光子上转换的蓝色激光光谱在半最大值处的优化全宽急剧缩小到大约6 nm，效率高达0.013％。
• Star-shaped oligofluorene truxene macromolecules – synthesis and properties as a function of alkyl chain length
  作者：Clara Orofino、Alexander L. Kanibolotsky、Peter J. Skabara

  DOI：10.24820/ark.5550190.p011.611

  日期：——