N,N'-bis(4-(trifluoromethyl)benzyl)-1,7-dibromo-perylene-3,4:9,10-bis(dicarboximide) | 1079757-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis(4-(trifluoromethyl)benzyl)-1,7-dibromo-perylene-3,4:9,10-bis(dicarboximide)
• 英文别名: 1,7-dibromo-N,N’-bis-(4-(trifluoromethyl)benzyl)-3,4,9,10-tetracarboxylperylene diimide；11,22-Dibromo-7,18-bis[[4-(trifluoromethyl)phenyl]methyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone；11,22-dibromo-7,18-bis[[4-(trifluoromethyl)phenyl]methyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• CAS: 1079757-48-4
• 化学式: C₄₀H₁₈Br₂F₆N₂O₄
• 分子量: 864.392
• InChiKey: BQNGCQSJMSVCMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  54
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,N'-bis(4-(trifluoromethyl)benzyl)-1,7-dibromo-perylene-3,4:9,10-bis(dicarboximide) 、 氰化锌 在 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以43%的产率得到N,N'-bis(4-(trifluoromethyl)benzyl)-1,7-dicyano-perylene-3,4:9,10-bis(dicarboximide)
  参考文献：
  名称：

  Organic n-Channel Transistors Based on Core-Cyanated Perylene Carboxylic Diimide Derivatives

  摘要：

  Five core-cyanated perylene carboxylic diimides end-functionalized with fluorine-containing linear and cyclic substituents have been synthesized and employed in the fabrication of air-stable n-channel organic thin-film field-effect transistors with carrier mobilities up to 0.1 cm(2)/Vs. The relationships between molecular structure, thin-film morphology, substrate temperature during vacuum deposition, transistor performance, and air stability have been investigated. Our experiments led us to conclude that the role of the fluorine functionalization in the air-stable n-channel operation of the transistors is different than previously thought.

  DOI：

  10.1021/ja074675e
• 作为产物：
  描述：

  3,4,9,10-苝四羧酸二酐 在 硫酸 、 溶剂黄146 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 65.0h， 生成 N,N'-bis(4-(trifluoromethyl)benzyl)-1,7-dibromo-perylene-3,4:9,10-bis(dicarboximide)
  参考文献：
  名称：

  迫使扭曲的 1,7-二溴苝二酰亚胺在固态下变平：原子会产生多大的变化

  摘要：

  在严重扭曲的 1,7-二溴苝二酰亚胺 (PDI) 的酰亚胺功能上引入低立体化学位阻的CH 2或 NH 间隔基，可以在固态下实现聚芳核意想不到的扁平化。粉末衍射和 DFT 计算提供了可靠的结构和能量细节，以及对稳定扁平 PDI 核的 π-π 相互作用的估计，抵消了扭曲的自然趋势。

  DOI：

  10.1002/anie.202310445

文献信息

• METHOD FOR PRODUCING ORGANIC FIELD-EFFECT TRANSISTORS
  申请人：Konemann Martin

  公开号：US20070259475A1

  公开（公告）日：2007-11-08

  A method for producing an organic field-effect transistor, comprising the steps of: a) providing a substrate comprising a gate structure, a source electrode and a drain electrode located on the substrate, and b) applying an n-type organic semiconducting compound to the area of the substrate where the gate structure, the source electrode and the drain electrode are located, wherein the n-type organic semiconducting compound is selected from the group consisting of compounds of the formula I wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, chlorine or bromine, with the proviso that at least one of these radicals is not hydrogen, Y 1 is O or NR a , wherein R a is hydrogen or an organyl residue, Y 2 is O or NR b , wherein R b is hydrogen or an organyl residue, Z 1 , Z 2 , Z 3 and Z 4 are O, where, in the case that Y 1 is NR a , one of the residues Z 1 and Z 2 may be a NR c group, where R a and R c together are a bridging group having 2 to 5 atoms between the terminal bonds, where, in the case that Y 2 is NR b , one of the residues Z 3 and Z 4 may be a NR d group, where R b and R d together are a bridging group having 2 to 5 atoms between the terminal bonds.
• US7910736B2
  申请人：——

  公开号：US7910736B2

  公开（公告）日：2011-03-22
• [EN] METHOD FOR PRODUCING ORGANIC FIELD-EFFECT TRANSISTORS<br/>[FR] PROCÉDÉ DE PRODUCTION DE TRANSISTORS À EFFET DE CHAMP ORGANIQUES
  申请人：BASF AG

  公开号：WO2007128774A1

  公开（公告）日：2007-11-15

  [EN] A method for producing an organic field-effect transistor, comprising the steps of: a) providing a substrate comprising a gate structure, a source electrode and a drain electrode located on the substrate, and b) applying an n-type organic semiconducting compound to the area of the substrate where the gate structure, the source electrode and the drain electrode are located, wherein the n-type organic semiconducting compound is selected from the group consisting of compounds of the formula (I) wherein R¹, R², R³ and R⁴ are independently hydrogen, chlorine or bromine, with the proviso that at least one of these radicals is not hydrogen, Y¹ is O or NR^a, wherein R^a is hydrogen or an organyl residue, Y² is O or NR^b, wherein R^b is hydrogen or an organyl residue, Z¹, Z², Z³ and Z⁴ are O, where, in the case that Y¹ is NR^a, one of the residues Z¹ and Z² may be a NR^c group, where R^a and R^c together are a bridging group having 2 to 5 atoms between the terminal bonds, where, in the case that Y² is NR^b, one of the residues Z³ and Z⁴ may be a NR^d group, where R^b and R^d together are a bridging group having 2 to 5 atoms between the terminal bonds.
  [FR] La présente invention concerne un procédé de production d'un transistor à effet de champ organique. A cet effet, a) on prend un substrat comprenant une structure de grille, une électrode source, et une électrode collectrce située sur le substrat, et b) un applique un composé organique semiconducteur de type n sur la zone du substrat occupée par la structure de grille, l'électrode source, et l'électrode collectrice. En l'occurrence, le composé organique semiconducteur de type n est choisi dans un groupe constitué de composés représentés par la formule (I). Dans cette formule, R¹, R², R³ et R⁴ sont indépendamment hydrogène, chlore ou brom (à la condition que l'un au moins de ces radicaux ne soit pas hydrogène). Y¹ est O ou NR^a, R^a étant hydrogène ou un résidu organyle. Y² est O ou NR^b, R^b étant hydrogène ou un résidu organyle. Z¹, Z², Z³ et Z⁴ sont O. Toutefois, si Y¹ est NR^a, l'un des résidus Z¹ et Z² peut être un groupe NR^c dans lequel R^a et R^c forment ensemble un groupe en pont portant 2 à 5 atomes entre les liaisons terminale bonds. En outre, su Y² est NR^b, l'un des résidus Z³ et Z⁴ peut être un groupe NR^d group. Et enfin, R^b et R^d forment ensemble un groupe en pont portant 2 à 5 atomes entre les liaisons terminales.
• Organic n-Channel Transistors Based on Core-Cyanated Perylene Carboxylic Diimide Derivatives
  作者：R. Thomas Weitz、Konstantin Amsharov、Ute Zschieschang、Esther Barrena Villas、Dipak K. Goswami、Marko Burghard、Helmut Dosch、Martin Jansen、Klaus Kern、Hagen Klauk

  DOI：10.1021/ja074675e

  日期：2008.4.1

  Five core-cyanated perylene carboxylic diimides end-functionalized with fluorine-containing linear and cyclic substituents have been synthesized and employed in the fabrication of air-stable n-channel organic thin-film field-effect transistors with carrier mobilities up to 0.1 cm(2)/Vs. The relationships between molecular structure, thin-film morphology, substrate temperature during vacuum deposition, transistor performance, and air stability have been investigated. Our experiments led us to conclude that the role of the fluorine functionalization in the air-stable n-channel operation of the transistors is different than previously thought.
• Forcing Twisted 1,7‐Dibromoperylene Diimides to Flatten in the Solid State: What a Difference an Atom Makes
  作者：Konstantis F. Konidaris、Marco Zambra、Francesco Giannici、Antonietta Guagliardi、Norberto Masciocchi

  DOI：10.1002/anie.202310445

  日期：2023.11.6

  The introduction of CH2 or NH spacers of low stereochemical hindrance on the imide function of heavily twisted 1,7-dibromoperylene diimides (PDIs), enables, in the solid state, the unexpected flattening of the polyaromatic cores. Powder diffraction and DFT calculations provided reliable structural and energetic details and an estimate of stabilizing π–π interactions of flat PDI cores, counterbalancing

  在严重扭曲的 1,7-二溴苝二酰亚胺 (PDI) 的酰亚胺功能上引入低立体化学位阻的CH 2或 NH 间隔基，可以在固态下实现聚芳核意想不到的扁平化。粉末衍射和 DFT 计算提供了可靠的结构和能量细节，以及对稳定扁平 PDI 核的 π-π 相互作用的估计，抵消了扭曲的自然趋势。