9-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole | 1334683-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
• 英文别名: 3,6-bis(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-9-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-carbazole；9-[2-[2-(2-Methoxyethoxy)ethoxy]ethyl]-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole；9-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole
• CAS: 1334683-10-1
• 化学式: C₃₁H₄₅B₂NO₇
• 分子量: 565.323
• InChiKey: FJWDTDNNCPZVNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,6-二溴咔唑 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 9-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
  参考文献：
  名称：

  聚（benzodithieno咪唑ALT -咔唑）基的π共轭共聚物：高选择性和灵敏的关断对Hg荧光探针2+

  摘要：

  在这项工作中，高发射性和可溶性的π共轭聚（benzodithieno咪唑ALT -咔唑）π共轭共聚物（P1和P2）已经通过的Pd（0）催化的合成Suzuki偶联由相应的单体聚合协议。为了在普通有机溶剂中增溶，已在苯并二硫代咪唑和咔唑单元的9位引入了庚基（在P1中）或2-（2-（2-（2-甲氧基乙氧基）乙氧基）乙基（在P2中）取代基。通过多核NMR光谱以及通过四检测器GPC研究显示分子量（M n）的16.5 kDa和14.3 kDa的多分散指数分别为1.36和1.31。作为分子荧光效应的关闭荧光探针，发射的π共轭聚合物对Hg 2+离子显示出显着的选择性和灵敏度，而不受其他竞争性金属离子的干扰。已进行了详细的光物理和传感研究，以了解聚合物与金属离子相互作用的见解，该现象与π共轭聚合物的选择性荧光猝灭有关。通过确定模型探针（M1）的前沿分子轨道和HOMO-LUMO能级，已经进行了DFT研究以了解

  DOI：

  10.1016/j.polymer.2018.10.069

文献信息

• Parameters influencing the molecular weight of 3,6-carbazole-based D-π-A-type copolymers
  作者：Yuanhe Fu、Jinseck Kim、Ayyanar Siva、Won Suk Shin、Sang-jin Moon、Taiho Park

  DOI：10.1002/pola.24877

  日期：2011.10.15

  AbstractCondensation copolymerization reactions of carbazole 3,6‐diboronate with 4,7‐bis(5‐bromo‐2‐thienyl)‐2,1,3‐benzothiadiazole (DTBT) only produce low‐molecular‐weight donor (D)‐π‐acceptor (A) copolymers. High‐molecular‐weight copolymers for use in optoelectronic devices are necessary for achieving extended π‐conjugation and for controlling the copolymer processibility. To elucidate the cause of the persistently low molecular weight, we synthesized three 3,6‐carbazole‐based D‐A copolymers using copolymerizations of N‐9′‐heptadecanyl‐3,6‐carbazole with DTBT, N‐9′2‐[2‐(2‐methoxy‐ethoxy)‐ethoxy]‐ethyl}‐3,‐6‐carbazole with DTBT, and N‐9′‐heptadecanyl‐3,6‐carbazole with alkyl‐substituted DTBT. We investigated several parameters for their influence on molecular copolymer weight, including the conformation of the chain during growth, the solubility of the monomers, and the dihedral angles between the donor and acceptor units. Size exclusion chromatography, UV–vis absorption spectroscopy, and computational studies revealed that the low molecular weights of 3,6‐carbazole‐based D‐A copolymers resulted from conjugation breaks and the resulting high coplanarity, which led to strong interactions between polymer chains. These interactions limited formation of high‐molecular‐weight‐copolymers during copolymerization. The strong intermolecular interactions of the 3,6‐carbazole moiety were exploited by incorporating 3,6‐carbazole units into poly[9′,9′‐dioctyl‐2,7‐flourene‐alt‐5,5‐(4′,7′‐di‐2‐thienyl‐2′,1′,3′‐benzothiadiazole)] prepared from 9′,9′‐dioctyl‐2,7‐flourene and DTBT. Interestingly, the number average molecular weight increased gradually with increasing 2,7‐fluorene monomer content but the number of conjugation breaks was a range of 6–7. The hole mobilities of the copolymers were studied for comparison purposes. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011
• Poly(benzodithieno-imidazole-alt-carbazole) based π-conjugated copolymers: Highly selective and sensitive turn-off fluorescent probes for Hg2+
  作者：Dipanjan Giri、Arindam Bankura、Sanjib K. Patra

  DOI：10.1016/j.polymer.2018.10.069

  日期：2018.12

  common organic solvents, heptyl (in P1) or 2-(2-(2-methoxyethoxy)ethoxy)ethyl (in P2) substituents have been introduced at benzodithieno-imidazole and 9-position of carbazole unit. The well-defined and soluble π-conjugated polymers have been characterized by multinuclear NMR spectra as well as by tetradetector GPC studies showing molecular weight (Mn) of 16.5 and 14.3 kDa with the polydispersity indices

  在这项工作中，高发射性和可溶性的π共轭聚（benzodithieno咪唑ALT -咔唑）π共轭共聚物（P1和P2）已经通过的Pd（0）催化的合成Suzuki偶联由相应的单体聚合协议。为了在普通有机溶剂中增溶，已在苯并二硫代咪唑和咔唑单元的9位引入了庚基（在P1中）或2-（2-（2-（2-甲氧基乙氧基）乙氧基）乙基（在P2中）取代基。通过多核NMR光谱以及通过四检测器GPC研究显示分子量（M n）的16.5 kDa和14.3 kDa的多分散指数分别为1.36和1.31。作为分子荧光效应的关闭荧光探针，发射的π共轭聚合物对Hg 2+离子显示出显着的选择性和灵敏度，而不受其他竞争性金属离子的干扰。已进行了详细的光物理和传感研究，以了解聚合物与金属离子相互作用的见解，该现象与π共轭聚合物的选择性荧光猝灭有关。通过确定模型探针（M1）的前沿分子轨道和HOMO-LUMO能级，已经进行了DFT研究以了解