并五苯-N-亚磺酰基-氨基甲酸叔丁酯 | 794586-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 中文名称: 并五苯-N-亚磺酰基-氨基甲酸叔丁酯
• 中文别名: 并五苯-N-亚磺酰基-叔丁基氨基甲酸酯
• 英文名称: Pentacene-N-sulfinyl-tert-butylcarbamate
• 英文别名: tert-butyl 23-oxo-23λ4-thia-24-azahexacyclo[10.10.2.02,11.04,9.013,22.015,20]tetracosa-2,4,6,8,10,13,15,17,19,21-decaene-24-carboxylate
• CAS: 794586-44-0
• 化学式: C₂₇H₂₃NO₃S
• 分子量: 441.551
• InChiKey: VQUHUWBRYQBGLV-UHFFFAOYSA-N

物化性质

• 熔点：
  >300°C
• 沸点：
  644.7±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)
• 溶解度：
  THF中的溶解度：1mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

制备方法与用途

用途：这是一种极易溶于非极性有机溶剂（如卤化溶剂、THF）的可光致图案并五苯前体。在薄膜（例如旋涂膜）中，通过在150℃氮气氛围下加热1小时可以转化为并五苯。

可以通过在光酸产生剂（如531014）存在下暴露于紫外线，然后进行短暂的加热处理（130℃下5分钟），并洗掉未转化的前体，来将旋涂的并五苯前体薄膜图案化。

采用该前体溶液加工制造的有机薄膜晶体管表现出迁移率为0.13 cm²V^-1s^-1和开关比为2×10⁵。

反应信息

• 作为产物：
  描述：

  氨基甲酸叔丁酯 在 [Pd(dppp)(PhCN)2](BF4)2 、 N-(chlorosulfinyl)imidazole 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 5.0h， 生成 并五苯-N-亚磺酰基-氨基甲酸叔丁酯
  参考文献：
  名称：

  A Photopatternable Pentacene Precursor for Use in Organic Thin-Film Transistors

  摘要：

  We demonstrate that modifying pentacene to incorporate an acid-labile moiety into its molecular structure leads to a new precursor that can be easily deposited, photopatterned, and processed via wet-chemical methods to produce organic semiconducting devices exhibiting good electrical characteristics. Acidic conditions produced by ultraviolet illumination of a co-deposited photoacid generator greatly accelerate the local conversion of this N-sulfinyl-tert-butylcarbamate pentacene adduct back to pentacene. Photopatterned thin-film transistors exhibit carrier mobilities in excess of 0.1 cm2 V-1 s-1, making this an attractive precursor for fabrication of large-area organic electronics via solution-phase methods.

  DOI：

  10.1021/ja045228r

文献信息

• PHOTOELECTRIC CONVERSION DEVICE AND SOLAR CELL USING THE SAME
  申请人：AKIYAMA Seiji

  公开号：US20120211082A1

  公开（公告）日：2012-08-23

  There is provides a photoelectric conversion device material which can be used as an electrode buffer material for a solar cell or the like and can improve durability while maintaining the interaction with an electrode and mobility; a photoelectric conversion device using the photoelectric conversion device material; and a solar cell using the photoelectric conversion device. A photoelectric conversion device containing a buffer layer and an active layer, wherein the buffer layer contains a compound represented by the following general formula (I), the active layer contains an n-type semiconductor, and the n-type semiconductor is a compound having a solubility in toluene of 0.5% by weight or more at 25° C. and having an electron mobility of 1.0×10 −6 cm 2 /Vs or more.

  提供了一种光电转换器件材料，可用作太阳能电池或类似器件的电极缓冲材料，可以提高耐久性，同时保持与电极的相互作用和移动性；使用该光电转换器件材料的光电转换器件；以及使用该光电转换器件的太阳能电池。光电转换器件包含缓冲层和活性层，其中缓冲层包含由下列通式（I）表示的化合物，活性层包含n型半导体，且该n型半导体在25℃时在甲苯中的溶解度为0.5%或更高，并具有1.0×10−6cm2/Vs或更高的电子迁移率。
• METHOD FOR PRODUCING ORGANIC PHOTOELECTRIC CONVERSION DEVICE AND ORGANIC PHOTOELECTRIC CONVERSION DEVICE
  申请人：Aramaki Shinji

  公开号：US20090308458A1

  公开（公告）日：2009-12-17

  The objects are to provide a method for producing a durable organic photoelectric conversion device by a coating process or to produce an organic photoelectric conversion device superior in photoelectric conversion characteristics to the conventional devices. In the production method for an organic photoelectric conversion device including a substrate, a pair of electrodes which are formed on the substrate and at least one of which is transparent, and an active layer formed between the pair of electrodes, the active layer is formed by coating; and the active layer contains a pigment
• US9136489B2
  申请人：——

  公开号：US9136489B2

  公开（公告）日：2015-09-15
• A Photopatternable Pentacene Precursor for Use in Organic Thin-Film Transistors
  作者：Kevin P. Weidkamp、Ali Afzali、Rudolf M. Tromp、Robert J. Hamers

  DOI：10.1021/ja045228r

  日期：2004.10.1

  We demonstrate that modifying pentacene to incorporate an acid-labile moiety into its molecular structure leads to a new precursor that can be easily deposited, photopatterned, and processed via wet-chemical methods to produce organic semiconducting devices exhibiting good electrical characteristics. Acidic conditions produced by ultraviolet illumination of a co-deposited photoacid generator greatly accelerate the local conversion of this N-sulfinyl-tert-butylcarbamate pentacene adduct back to pentacene. Photopatterned thin-film transistors exhibit carrier mobilities in excess of 0.1 cm2 V-1 s-1, making this an attractive precursor for fabrication of large-area organic electronics via solution-phase methods.