3,6-bis(4-bromophenyl)-1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole-2,5-dione | 1379525-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3,6-bis(4-bromophenyl)-1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole-2,5-dione
• 英文别名: 3,6-Bis(4-bromophenyl)-1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole-2,5-dione
• CAS: 1379525-70-8
• 化学式: C₃₈H₃₄Br₂N₂O₂
• 分子量: 710.508
• InChiKey: HLITWSXBUWNZFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N'-di-t-butylphenyloxamide 在 五氯化磷 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 27.5h， 生成 3,6-bis(4-bromophenyl)-1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole-2,5-dione
  参考文献：
  名称：

  Deeply Colored Polymers Containing 1,3,4,6-Tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (IsoDPP) Units in the Main Chain

  摘要：

  Synthesis and characteristic properties of polymers P1-P4 containing 1,3,4,6-tetraarylated pyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP) units in the main chain are described. PI and P2 were prepared upon palladium-catalyzed polycondensation of 3,6-bis(4-bromophenyl)-1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole-2,S-dione (M1) or 1,4-bis(4-bromophenyl)-3,6-bis(4-tert-butylphenyl)pyrrolo[3,2-b]-pyrrole-2,5-dione (M2) and 2,2'-(9,9-dihexyl-9H-fluoren-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (M4), while P3 and P4 were synthesized upon polycondensation of 3,6-bis(5-bromothien-2-yl)-1,4-bis(4-dodecylphenyl)pyrrolo[3,2-b]pyrrole-2,5-dione (M3) and 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene (MS) or 9-(2-ethylhexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole (M6). Deeply colored polymers with molecular weights between 3.5 and 22, kDa were obtained. The polymers were soluble in common organic solvents such as dichloromethane, chloroform, and tetrahydrofuran. All polymers exhibit broad absorption bands with high extinction coefficients (epsilon > 2 x 10(4) L mol(-1) cm(-1)) but weak fluorescence, the quantum yields being below 1%. Although P1 and P2 are isomers, their optical properties are rather different. P1 with polyconjugated backbone exhibits an absorption maximum at 409 nm, while P2 has a maximum at 360 nm due to interruption of pi-conjugation at the lactam N atoms. The presence of thienyl-isoDPP units in the backbone causes a red-shift of the absorption to 489 nm (P3) and 435 nm (P4). All polymers exhibit nearly irreversible oxidation and reduction behavior. Bandgaps of the polymers with phenyl-substituted isoDPP units (PI and P2) are at about 2 eV, while those of polymers with thienyl-substituted isoDPP (P3 and P4) are at about 1.5 eV.

  DOI：

  10.1021/ma300483u

文献信息

• Deeply Colored Polymers Containing 1,3,4,6-Tetraarylpyrrolo[3,2-<i>b</i>]pyrrole-2,5-dione (IsoDPP) Units in the Main Chain
  作者：Irina Welterlich、Olga Charov、Bernd Tieke

  DOI：10.1021/ma300483u

  日期：2012.6.12

  Synthesis and characteristic properties of polymers P1-P4 containing 1,3,4,6-tetraarylated pyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP) units in the main chain are described. PI and P2 were prepared upon palladium-catalyzed polycondensation of 3,6-bis(4-bromophenyl)-1,4-bis(4-tert-butylphenyl)pyrrolo[3,2-b]pyrrole-2,S-dione (M1) or 1,4-bis(4-bromophenyl)-3,6-bis(4-tert-butylphenyl)pyrrolo[3,2-b]-pyrrole-2,5-dione (M2) and 2,2'-(9,9-dihexyl-9H-fluoren-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (M4), while P3 and P4 were synthesized upon polycondensation of 3,6-bis(5-bromothien-2-yl)-1,4-bis(4-dodecylphenyl)pyrrolo[3,2-b]pyrrole-2,5-dione (M3) and 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene (MS) or 9-(2-ethylhexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole (M6). Deeply colored polymers with molecular weights between 3.5 and 22, kDa were obtained. The polymers were soluble in common organic solvents such as dichloromethane, chloroform, and tetrahydrofuran. All polymers exhibit broad absorption bands with high extinction coefficients (epsilon > 2 x 10(4) L mol(-1) cm(-1)) but weak fluorescence, the quantum yields being below 1%. Although P1 and P2 are isomers, their optical properties are rather different. P1 with polyconjugated backbone exhibits an absorption maximum at 409 nm, while P2 has a maximum at 360 nm due to interruption of pi-conjugation at the lactam N atoms. The presence of thienyl-isoDPP units in the backbone causes a red-shift of the absorption to 489 nm (P3) and 435 nm (P4). All polymers exhibit nearly irreversible oxidation and reduction behavior. Bandgaps of the polymers with phenyl-substituted isoDPP units (PI and P2) are at about 2 eV, while those of polymers with thienyl-substituted isoDPP (P3 and P4) are at about 1.5 eV.