N-dodecyl-2,7-dibromodithieno[3,2-f:2',3'-h]phthalimide | 1301741-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-dodecyl-2,7-dibromodithieno[3,2-f:2',3'-h]phthalimide
• 英文别名: 4,14-Dibromo-9-dodecyl-3,15-dithia-9-azatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,11,13-pentaene-8,10-dione；4,14-dibromo-9-dodecyl-3,15-dithia-9-azatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,11,13-pentaene-8,10-dione
• CAS: 1301741-22-9
• 化学式: C₂₄H₂₇Br₂NO₂S₂
• 分子量: 585.424
• InChiKey: JGSRFNPUAONUIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-dodecyl-2,7-dibromodithieno[3,2-f:2',3'-h]phthalimide 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 溶剂黄146 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 48.0h， 生成 N-dodecyl-2,7-bis(5-bromothiophen-2-yl)dithieno[3,2-f:2',3'-h]-phthalimide
  参考文献：
  名称：

  Conjugated Polymers Based on a New Building Block: Dithienophthalimide

  摘要：

  A new fused-ring building block dithieno[3,2-f:2',3'-h]-phthalimide was synthesized and used in synthesis of conjugated polymers. On the basis of this building block, we designed and synthesized a series of conjugated copolymers containing electron-rich unit benzo[1,2-b:4,5-b']dithiophene (P1 and P2) or with electron-deficient unit 2,2'-bithiazole (P3 and P4) or benzo[c][1,2,5]thiadiazole (P5) and homopolymer (P6). P1 and P4 P6 have good solubility in common organic solvents, while P2 and P3 have poor solubility. P1-P6 exhibit good thermal stability with 5% weight loss temperatures of 193-417 degrees C. PI P6 in films exhibit absorption maxima of 482-532 nm with optical bandgaps of 1.88-2.25 eV and weak emission peaked at 597-721 nm. P1-P6 have estimated HOMOs of -5.3 to -6.2 eV and LUMOs of -2.8 to -3.4 eV. The optical properties and HOMO/LUMO levels are influenced by the comonomers. The polymer solar cells based on PI:P1:PC6IBM (1:1, w/w) exhibit preliminary power conversion efficiency of 0.30% under an AM 1.5 simulated solar light at 100 mW/cm(2).

  DOI：

  10.1021/ma2003097
• 作为产物：
  描述：

  3,4-dibromo-1-dodecylpyrrole-2,5-dione 在 iron(III) chloride 、 四(三苯基膦)钯 、 溴 、 potassium carbonate 作用下， 以 硝基甲烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 64.0h， 生成 N-dodecyl-2,7-dibromodithieno[3,2-f:2',3'-h]phthalimide
  参考文献：
  名称：

  Conjugated Polymers Based on a New Building Block: Dithienophthalimide

  摘要：

  A new fused-ring building block dithieno[3,2-f:2',3'-h]-phthalimide was synthesized and used in synthesis of conjugated polymers. On the basis of this building block, we designed and synthesized a series of conjugated copolymers containing electron-rich unit benzo[1,2-b:4,5-b']dithiophene (P1 and P2) or with electron-deficient unit 2,2'-bithiazole (P3 and P4) or benzo[c][1,2,5]thiadiazole (P5) and homopolymer (P6). P1 and P4 P6 have good solubility in common organic solvents, while P2 and P3 have poor solubility. P1-P6 exhibit good thermal stability with 5% weight loss temperatures of 193-417 degrees C. PI P6 in films exhibit absorption maxima of 482-532 nm with optical bandgaps of 1.88-2.25 eV and weak emission peaked at 597-721 nm. P1-P6 have estimated HOMOs of -5.3 to -6.2 eV and LUMOs of -2.8 to -3.4 eV. The optical properties and HOMO/LUMO levels are influenced by the comonomers. The polymer solar cells based on PI:P1:PC6IBM (1:1, w/w) exhibit preliminary power conversion efficiency of 0.30% under an AM 1.5 simulated solar light at 100 mW/cm(2).

  DOI：

  10.1021/ma2003097

文献信息

• DITHIENOPHTHALIMIDE SEMICONDUCTOR POLYMERS
  申请人：Noguchi Hiroyoshi

  公开号：US20140142265A1

  公开（公告）日：2014-05-22

  The invention concerns apolymer of the formula (I): wherein: M1 is an optionally substituted dithienophthalimide formula (II): wherein: X is N or C—R, wherein R is H or a C 1 -C 40 alkyl group, R 2 , at each occurrence, is independently selected from H, a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 1-40 haloalkyl group, and a monocyclicor polycyclic moiety, wherein: each of the C 1-40 alkyl group, the C 2-40 alkenyl group, and the C 1-40 haloalkyl group can be optionally substituted with 1-10 substituents independently selected from a halogen, CN, —NO 2 , OH, NH 2 , —NH(C 1-20 alkyl), N(C 1-20 alkyl) 2 , —S(O) 2 OH, —CHO, —C(O)—C 1-20 alkyl, —C(O)OH, —C(O)—OC 1-20 alkyl, —C(O)NH 2 , —C(O)NH—C 1-20 alkyl, —C(O)N(C 1-20 alkyl) 2 , —OC 1-20 alkyl, —SiH 3 , —SiH(C 1-20 alkyl) 2 , —SiH 2 (C 1-20 alkyl), and —Si(C 1-20 alkyl) 3 ; and the monocyclic or polycyclic moiety can be covalently bonded to the imide nitrogen via an optional linker, and can be optionally substituted with 1-5 substituentsindependently selected from a halogen, oxo, —CN, —NO 2 , OH, ═C(CN) 2 , —NH 2 , —NH(C 1-20 alkyl), N(C 1-20 alkyl) 2 , —S(O) 2 OH, —CHO, —C(O)OH, —C(O)—C 1-20 alkyl, —C(O)—OC 1-20 alkyl, —C(O)NH 2 , —C(O)NH—C 1-20 alkyl, —C(O)N(C 1-20 alkyl) 2 , —SiH 3 , —SiH(C 1-20 alkyl) 2 , —SiH 2 (C 1-20 alkyl), —Si(C 1-20 alkyl) 3 , —O—C 1-20 alkyl, —O—C 1-20 alkenyl, —O—C 1-20 haloalkyl, C 1-20 alkyl, C 1-20 alkenyl, C 1-20 haloalkyl, C 7-20 arylalkyl, C 6-20 aryloxy and C 7-20 arylcarbonyl. M 2 is a repeating unit comprising one or more cyclic moieties; and n is an integer between 2 and 5,000.
• US9006725B2
  申请人：——

  公开号：US9006725B2

  公开（公告）日：2015-04-14