1,1'-bis(tert-butoxycarbonyl)-bis(6,6'-dibromooindolidene)-3,3'-dione | 1444613-29-9

• 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: 1,1'-bis(tert-butoxycarbonyl)-bis(6,6'-dibromooindolidene)-3,3'-dione
• 英文别名: di-tert-butyl 6,6'-dibromo-3,3'-dioxo[2,2'-biindolinylidene]-1,1'-dicarboxylate；(E)-di-tert-butyl-6,6'-dibromo-2,2'-dioxo-[3,3'-biindolinylidene]-1,1'-dicarboxylate；di-tert-butyl (2E)-6,6′-dibromo-3,3′-dioxo-2,2′-biindole-1,1’(3H,3’H)-dicarboxylate；bis-tBOC-6,6'-dibromooindigo；Di-t-butyl (2e)-6,6'-dibromo-3,3'-dioxo-2,2'-biindole-1,1'(3h,3'h)-dicarboxylate；tert-butyl (2E)-6-bromo-2-[6-bromo-1-[(2-methylpropan-2-yl)oxycarbonyl]-3-oxoindol-2-ylidene]-3-oxoindole-1-carboxylate
• CAS: 1444613-29-9
• 化学式: C₂₆H₂₄Br₂N₂O₆
• 分子量: 620.294
• InChiKey: VSGXSKHDPVZYJR-FMQUCBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1'-bis(tert-butoxycarbonyl)-bis(6,6'-dibromooindolidene)-3,3'-dione 以 甲苯 为溶剂， 生成 C₂₆H₂₄Br₂N₂O₆
  参考文献：
  名称：

  N，N'-二（叔丁氧羰基）靛蓝的可逆光化学异构化

  摘要：

  我们上的光物理报告Ñ，Ñ ' -二（吨氧羰基）靛蓝（叔BOC靛蓝），发现可逆光化学反式-顺和顺-反异构化反应继续进行具有高量子产率（0.10-0.46）。在500-600 nm范围内吸收波长会引起反式-顺式异构，而蓝光则导致反式的顺-反式过程。与其父母的靛蓝一样，反式-BOC靛蓝的荧光产量低（〜1×10 –3），而顺式的异构体没有可测量的发射。这些化合物是可光异构的靛类染料的第一个实例，其中光化学异构性有效地超过了辐射衰变过程。尽管靛蓝染料通常在有机溶剂中的溶解性较差，但tBOC靛蓝染料可以以高达8 w％的浓度溶解在常见的有机溶剂（如丙酮）中。此外，与其他可光异构化的靛蓝不同，tBOC靛蓝对质子和电子供体的猝灭不敏感。这些特征，再加上相对较低能量的光子（〜2 eV）引起的可逆光异构现象的高量子产率，使得tBOC靛蓝衍生物对于光致变色应用（如光机械致动材料）具有潜在的吸引力。

  DOI：

  10.1021/jp512346z
• 作为产物：
  描述：

  4-溴-2-硝基苯甲醛 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1,1'-bis(tert-butoxycarbonyl)-bis(6,6'-dibromooindolidene)-3,3'-dione
  参考文献：
  名称：

  An indigo-based polymer bearing thermocleavable side chains for n-type organic thin film transistors

  摘要：

  基于靛蓝的新型n型半导体聚合物被合成，并作为有机薄膜晶体管的活性层。该聚合物含有具有热裂解性质的叔丁氧羰基（t-Boc）基团。

  DOI：

  10.1039/c5tc00512d

文献信息

• An indigo-based polymer bearing thermocleavable side chains for n-type organic thin film transistors
  作者：Chang Guo、Jesse Quinn、Bin Sun、Yuning Li

  DOI：10.1039/c5tc00512d

  日期：——

  A new n-type semiconducting polymer based on indigo with thermocleavable tert-butoxycarbonyl (t-Boc) groups was synthesized and used as an active layer in organic thin film transistors.

  基于靛蓝的新型n型半导体聚合物被合成，并作为有机薄膜晶体管的活性层。该聚合物含有具有热裂解性质的叔丁氧羰基（t-Boc）基团。
• A facile protection–deprotection route for obtaining indigo pigments as thin films and their applications in organic bulk heterojunctions
  作者：Eric Daniel Głowacki、Gundula Voss、Kadir Demirak、Marek Havlicek、Nevsal Sünger、Aysu Ceren Okur、Uwe Monkowius、Jacek Gąsiorowski、Lucia Leonat、Niyazi Serdar Sariciftci

  DOI：10.1039/c3cc42889c

  日期：——

  Indigo and its derivatives are industrially-important dyes known for centuries. The low solubility of these compounds limits their applications and hinders potential synthetic chemistry using indigo as a building-block. Herein we report attachment of the tert-butoxy carbonyl (tBOC) thermolabile protecting group to indigos, allowing their processing into neat thin films as well as mixed films with a semiconducting polymer. Photoinduced charge transfer is observed to and from these pigments and the polymer.

  靛蓝及其衍生物是几个世纪以来众所周知的重要工业染料。这些化合物的低溶解度限制了它们的应用，并阻碍了以靛蓝为基础的潜在合成化学。在此，我们报告了将叔丁氧基羰基（tBOC）热稳定保护基团附着到靛蓝上，从而将其加工成纯净薄膜以及与半导体聚合物混合薄膜的情况。在这些颜料和聚合物之间观察到了光诱导电荷转移。
• Nanowires of indigo and isoindigo-based molecules with thermally removable groups
  作者：Chunchen Liu、Wenzhan Xu、Qifan Xue、Ping Cai、Lei Ying、Fei Huang、Yong Cao

  DOI：10.1016/j.dyepig.2015.10.003

  日期：2016.2

  In this manuscript, indigo and isoindigo-based pi-conjugated molecules with thermal removable tert-butoxycarbonyl (t-Boc) side groups were designed and synthesized. It was noted that the t-Boc side groups can be eliminated in nearly quantitative yields after thermal treatment at 200 degrees C for 15 min, as confirmed by thermogravimetric analysis and Fourier transform infrared spectroscopy. From the thermal treated solution of isoindigo-based molecule DTIIC8C12 in the co-solvent of 1,2-dichlorobenzene/pyridine with volume ratio of 10/90, one-dimensional nanowires can be formed due to the hydrogen bonding assisted self-assembly. The afforded nanowires exhibited a moderate hole mobility of 1.3 x 10(-3) cm(2) V-1 s(-1), as estimated from the organic field effect transistors. These observations illustrated that the utilization of thermal removable side chain functionalized conjugated polymers can be an effective strategy for developing conjugated polymers-with impressive charge carrier transport. (C) 2015 Elsevier Ltd. All rights reserved.
• INDIGO-BASED POLYMERS FOR USE IN SWCNTS ELECTRONICS
  申请人：National Research Council of Canada

  公开号：US20210293734A1

  公开（公告）日：2021-09-23

  A compound of Formula (0): where Ar is one or more substituted or unsubstituted aromatic units, R is independently H, F, CN, a C 1 -C 20 linear or branched aliphatic group or a C 1 -C 20 linear or branched aliphatic acyl group, and n is an integer 3 or greater, is useful for sorting and dispersing carbon nanotubes (CNTs) and for producing printed electronic devices (e.g. CO 2 sensors, TFTs) in which the CNTs are functionalized with the compound.
• PHOTO-PATTERNABLE ORGANIC SEMICONDUCTOR (OSC) POLYMERS AND METHODS OF FORMATION AND APPLICATIONS THEREOF
  申请人：Corning Incorporated

  公开号：US20220119591A1

  公开（公告）日：2022-04-21

  A method, includes: reacting at least one donor group with at least one protected acceptor group to form a plurality of protecting group-containing OSC polymers; removing the protecting group from the plurality of protecting group-containing OSC polymers to form H-bonding sites; and fusing the H-bonding sites of a first OSC polymer backbone with H-bonding sites of a second OSC polymer backbone to form π-π interactions between conjugated OSC polymers.