3,6-di-tert-butyl-9-(4-iodophenyl)-9H-carbazole | 255829-32-4

• 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: 3,6-di-tert-butyl-9-(4-iodophenyl)-9H-carbazole
• 英文别名: 3,6-bis(tert-butyl)-9-(4-iodophenyl)carbazole；3,6-di-tert-butyl-9-(4-iodophenyl)carbazole；3,6-di-tert-butyl-9-(p-iodophenyl)carbazole；3,6-di-tert-butyl-N-(4-iodophenyl)carbazole；9H-Carbazole, 3,6-bis(1,1-dimethylethyl)-9-(4-iodophenyl)-；3,6-ditert-butyl-9-(4-iodophenyl)carbazole
• CAS: 255829-32-4
• 化学式: C₂₆H₂₈IN
• 分子量: 481.42
• InChiKey: YQYSNSRGPZHPPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  532.7±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,6-di-tert-butyl-9-(4-iodophenyl)-9H-carbazole 在 正丁基锂 、 硼酸三乙酯 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 27.5h， 以59%的产率得到(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)boronic acid
  参考文献：
  名称：

  High Triplet Energy Polymer as Host for Electrophosphorescence with High Efficiency

  摘要：

  We report the conjugated polymer P( tBu-CBP) as a host with high triplet energy ( E-T 2.53 eV) and suitable HOMO ( 5.3 eV) and LUMO ( 2.04 eV) energy levels. Upon doping with green and red emission Ir-complexes, it gives devices with high luminous and external quantum efficiencies for green emission ( 23.7 cd/A, 6.57%) and for red emission ( 5.1 cd/A, 4.23%), respectively, and low turn-on voltage ( 3 V). For both devices, the efficiencies are higher than those of the corresponding devices with the same backbone P( 3,6-Cz) as a host by a factor of 4, even though the latter has an E-T ( 2.6 eV) slightly higher than that of the former. The results reflect that, in phosphorescent devices, the difference in E-T between the host and guest is not the only factor that determines the device efficiency, and the present side group modification via the 9 position of carbazole also plays an important role, which allows a tuning of HOMO and LUMO levels to provide more balance in electron and hole fluxes and provides prevention from formation of excimer.

  DOI：

  10.1021/ja060936t
• 作为产物：
  描述：

  9-(4-溴苯基)-3,6-二-叔丁基-9h-咔唑 在 正丁基锂 、 全氟己基碘烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以65%的产率得到3,6-di-tert-butyl-9-(4-iodophenyl)-9H-carbazole
  参考文献：
  名称：

  Synthesis and Crystal Structures of Isolable Terminal Aryl Hexatriyne and Octatetrayne Derivatives: Ar−(C≡C)_nH (n = 3, 4)

  摘要：

  Unprecedented stability has been observed in terminal aryl hexatriyne and terminal aryl octatetrayne derivatives by judicious choice of a bulky, nonplanar headgroup [viz., 4-(3,6-di-tert-butyl-N-carbazolyl)phenyl] which hinders topochemical intermolecular interactions in the crystal lattice.

  DOI：

  10.1021/ol801121p

文献信息

• Evaluation of bis-cyclometalated alkynylgold(<scp>iii</scp>) sensitizers for water photoreduction to hydrogen
  作者：Zhen-Tao Yu、Xiao-Le Liu、Yong-Jun Yuan、Yong-Hui Li、Guang-Hui Chen、Zhi-Gang Zou

  DOI：10.1039/c6dt03044k

  日期：——

  conditions, hydrogen evolution took place through a photochemical route with the highest efficiency and with a turnover number (TON) of up to 1441.5 relative to the sensitizer over 24 hours. In the initial photochemical path, the reductive quenching of the excited gold(III) complex by TEOA due to the latter's greater concentration in the system followed by electron transfer to the catalyst species is proposed

  尽管有数十年的兴趣，但用于水生产氢气的明确定义的金敏化剂仍然极为罕见，目前仅限于基于钌，铱或铂络合物的系统。这份报告详细的串联中性环金属金（的合成和表征III类型[（RC ^ N ^ CR）的Au（C的复合物）CR'）]（R = H或叔丁基基团; R' （芳基基团）被认为是在光诱导的电子转移反应中充当收割材料的良好候选者。我们建立了在[Co（2,2'-联吡啶）3 ] Cl 2存在下使用这些金（III）配合物作为光敏剂（PSs）在可再生氢生产中的功效。或[Rh（4,4'-二叔丁基-2,2'-联吡啶）3 ]（PF 6）3作为H 2演化催化剂，而三乙醇胺（TEOA）作为牺牲电子给体在丙酮-水中解决方案。所有复合物均具有活性，并且在光催化H 2生成活性方面比其他候选化合物增加三倍以上。在最佳反应条件下，相对于敏化剂，在24小时内通过光化学途径以最高的效率和高达1441.5的周转数（TON）析氢。在
• One-pot two-step synthesis of N-arylcarbazole-based skeleton
  作者：Sheng Tao、Ning Liu、Bin Dai

  DOI：10.1039/c5ra26698j

  日期：——

  A highly site-selective, one-pot, sequential C–N and C–C bond forming process was developed, affording a carbazole-based skeleton that contains biphenyl and diarylacetylene cores. The success of this process is attributed to the use of fluorinated iodoarenes as the starting material, the fluorine group of which preferentially reacts with carbazole. The subsequent coupling of the intermediate iodinated

  开发了一种高度位点选择性，一锅，顺序的C–N和C–C键形成工艺，从而提供了含有联苯和二芳基乙炔核心的咔唑骨架。该方法的成功归因于使用氟化碘代芳烃作为起始原料，其氟基团优先与咔唑反应。中间体碘代N-芳基咔唑与芳基硼酸或芳基乙炔的随后偶联产生所需产物。在不存在芳基硼酸或芳基乙炔的情况下，将中间体与过量的氟化碘代芳烃进行Pd催化的Ullmann偶联，从而在一锅法中得到Ullmann偶联产物。
• Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure–properties relationship
  作者：Lukáš Kerner、Katarína Gmucová、Jozef Kožíšek、Václav Petříček、Martin Putala

  DOI：10.1016/j.tet.2016.09.063

  日期：2016.11

  We devised and synthesized a series of electron-rich compounds featuring diphenylamine, carbazole or dibenzo[c,g]carbazole connected via phenylacetylene linkers to an aromatic central unit. The key synthetic step was a high yielding cross coupling reaction between halogenated (bi)naphthalene and organometallic reagents prepared in situ from terminal alkynes (side-arms). By masking one of the iodo functions

  我们设计并合成了一系列具有二苯胺，咔唑或二苯并[ c，g通过苯基乙炔连接基连接到芳族中心单元上的]咔唑。关键的合成步骤是卤化（双）萘与由末端炔烃（侧臂）就地制备的有机金属试剂之间的高产率交叉偶联反应。通过在侧臂前体中用二乙基三氮烯基掩盖碘官能之一，我们有效地避免了双胺化副产物的形成。尽管延长了一步，但与直接偶联途径相比，这种方法导致最终炔烃的收率更高。由计算证据支持的光谱和电化学测量结果表明，在1,4-二取代的萘骨架中的共轭优于1,5或2,6取代的核。与咔唑类似物相比，二苯胺衍生物更容易被氧化。
• Copper/β-diketone-catalysed N-arylation of carbazoles
  作者：Fei Chen、Ning Liu、Enhui Ji、Bin Dai

  DOI：10.1039/c5ra07690k

  日期：——

  A copper/β-diketone-catalysedN-arylation of carbazoles with aryl iodides is developed with broad substrate applicability and moderate to good yields.

  使用铜/β-二酮催化剂对碳酰胺与芳基碘化物进行N-芳基化反应，具有广泛的底物适用性和中等至良好的产率。
• Synthesis and Characterization of Monodendrons Based on 9-Phenylcarbazole
  作者：Zhengguo Zhu、Jeffrey S. Moore

  DOI：10.1021/jo991167h

  日期：2000.1.1

  A series of 9-phenylcarbazole ethynylene monodenrons have been prepared by palladium-catalyzed coupling reactions creating well-organized arrays of redox centers. The tert-butyl groups attached to the 3,6-positions of peripheral 9-phenylcarbazole monomers provide adequate solubility to a limited degree. Trimer and 7-mer monodendrons were prepared using a monomer with 3, 3-diethyltriazene at its focal

  已经通过钯催化的偶联反应制备了一系列9-苯基咔唑乙炔基单denrons，从而形成了组织良好的氧化还原中心阵列。连接至外围9-苯基咔唑单体的3,6-位的叔丁基可在有限的程度上提供足够的溶解度。使用在其焦点处带有3，3-二乙基三氮烯的单体制备三聚体和7-聚一聚体。然而，为了促进纯化，合成15聚体单枝二烯需要在其焦点处带有3-羟基-3-甲基-丁-1-炔基的单体作为末端乙炔官能团的掩蔽基团。尽管溶解度受到限制，但是发现高世代单树枝容易溶于高极化率的溶剂二硫化碳。